the CEO is obsessed with me and wants me to be his emotional support

by Alison Green on April 26, 2022

A reader writes:

Please help me understand what is going on with my role as an executive assistant to the CEO of my company. I’m struggling to understand if this sort of thing is normal and I wasn’t prepared for it or if something is actually wrong here. Some days are okay but I’m feeling increasingly uncomfortable, isolated, and smothered by my boss.

This will be long but I think anecdotes might add additional context, so I will format in bullet points for easy skimming.

• I was hired in 2019 as an administrative assistant. I quickly became close work buddies with the HR generalist. The CEO began to join our conversations and eventually our smoke breaks, though he doesn’t smoke. We became a friendly little triangle, though I occasionally felt that my boss did not approve of the amount of time that would get wasted while entertaining each other.

• After Covid shut down the offices and we all worked from home, the CEO continued to work from the office and would make very long video calls or start virtual meetings several times a day, to one or both of us at a time. This quickly became an annoyance and at one point I had spent over three hours in one day engaged in some sort of call or meeting with him. These meetings and phone calls were never work-related.

• He became obsessive and would call first thing in the morning, before I had even started working, and usually toward the end of my work day, often past my clock out time.

• Eventually there was a huge blow-up when it was discovered that the HR generalist was a pathological liar who was spreading horrible rumors, trying to get me fired, and committing tax fraud. She was let go.

• In July of 2020, I was approached by the CEO to undergo “career counseling” and he would be my mentor. We had one very strange meeting in which he spoke a lot about brutal honesty, holding nothing back, and advised me that this would be a painful but necessary process, while asking very personal questions about my childhood and family.

• During this time I was struggling with some things in my personal life and I disengaged from him as much as I was able to while remaining employed.

I now see this is going to be WAY TOO LONG if I type out all the history, so I’m going to fast forward to current day and get to the root of my issues.

• My CEO talks a lot about the role of an executive assistant, specifically that they are the one person who is focused entirely on the CEO and always has their eyes on them, and that he waited for years before I came along and he chose me.

• He requires more and more quality time with me, time in which we aren’t working but still during work hours, as part of the “emotional caretaking” that I am supposed to perform as his executive assistant.

• He makes me go on every single business trip he goes on, whether or not I have a professional task or reason to be there. We are currently at odds over a trip that would interfere with an important event in my personal life. He wants me to go on this trip with him even though I have no reason to be there and I would rather attend an induction ceremony to an honor society I was just invited to join.

Are these normal functions of an executive assistant? What does the relationship with an executive assistant and their executive look like? At this point I am so exhausted from managing my relationship with him that I have nothing left for my marriage. I’m very confused because he constantly talks about how lucky we are and how good we have it, which may be true for him, but I’m miserable.

Get out get out get out.

None of this is normal. I don’t know what’s driving your CEO’s behavior, but a lot of it sounds like grooming, some of it sounds like the way cults brainwash people, and none of it sounds like a normal CEO/assistant relationship. None of it.

Do some CEOs cross boundaries with the people who work for them? Sure. Some CEOs waste people’s time with overly social calls, not realizing or not caring that their employees won’t feel comfortable kicking them off the phone. Some CEOs are inappropriately demanding of their employees’ time in other ways too, like keeping them on the phone past the end of their workday.

But this goes way, way beyond that. Things that are huge red flags in your situation:

* You feel his interest in you has become obsessive and he needs to talk with you for hours a day, rarely for work reasons.

* He tried to rope you into a highly personal and highly suspect counseling process with him in which he wanted you to “hold nothing back” and talk about extremely intimate topics. This is not normal; if you described this in other contexts, it would sound similar to quite a few cult indoctrinations. (It’s also interesting to note that although he described it as “painful but necessary,” he doesn’t seem to have ever explained why such a thing would be necessary at work … and that’s because it never would be.)

* He has tried to convince you that it’s an inherent part of your job to give him intense and constant personal attention, when it’s not. Look at how much of the attention he wants from you has nothing to do with work, like those hours of phone calls on non-work topics. This isn’t about work; it’s about something obsessive within him, but he is trying to manipulate you into thinking your job requires it of you.

* His statement that he waited for years before you came along and he chose you … this is frankly rather frightening, particularly in the context of the rest of it, and again very culty.

* You’re feeling that he’s leaving you with nothing left for your marriage. That on its own would be a signal to get out. Combined with everything above, it’s likely exactly what he wants.

None of this is normal. All of it is alarming.

You asked what the relationship between an executive assistant and their executive should look like. To function well, that relationship does need to be a fairly close one — but it’s a work relationship, not a personal one. In a normal EA relationship, you’re supporting the exec’s work by doing things like ensuring they have the right material to prep for meetings, managing their calendar, triaging their work, ensuring action items aren’t dropped, dealing with administrative burdens so they don’t have to, being someone they can delegate tasks to, and sometimes helping them take the pulse of leaders and teams beneath them and sharing insights the executive might have missed.

There is a certain amount of emotional intimacy in the relationship when the job is done well, but it’s stuff like “I know she’s annoyed by how long her meetings go with Jane so I’m going to knock on the door and rescue her at 4” or “he always has a blind spot about how the sales folks will react to stuff like this, so I’m going to flag X concern for him.” It’s intimacy in service of the work. It’s all toward the goal of enabling the exec to be as productive and effective at their job as possible. It’s not about their emotional well-being.

What your CEO is asking of you isn’t in service of the work. He wants you to be his emotional caretaker because of his own emotional needs, to a point that sounds more reflective of something sick within him than anything having to do with his job.

But even if none of that convinces you (and people like him are very good at planting self-doubt in their targets): You are miserable. That alone is reason enough to get out.

Please leave as soon as you possibly can. Be prepared for a ton of resistance from him when you do; assume it will happen and don’t be deterred when it does. This is a situation where you should strongly consider blocking his number when you leave and not letting him know what you’ll be doing next (in fact, consider saying you’re moving out of the area) because he sounds like he may try to hold on even after you leave, and the more you can protect yourself from that, the better.

Read updates to this letter here and here.

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{ 591 comments }

{ 591 comments… read them below }

    1. Thin Mints didn't make me thin*

      Get whatever help you need — a therapist, your spouse, supportive friends — and get your resumes out there. This is not OK.

      1. GammaGirl1908*

        Run SCREAMING into the night. Flee. Immediately. Save yourself.

        ALLLLLLL the red flags ae waving wildly.

    2. Anonym*

      And pick up a copy of Gavin de Becker’s “Gift of Fear” while you’re at it. (It’s imperfect for several reasons, but valuable and relevant, not least in identifying ways in which this situation might escalate.)

      This is not hyperbole, OP. Your situation is genuinely alarming.

      1. irene adler*

        Yes to this! Cuz part II- the stalking by former boss- will happen. He’s not gonna go away easily.

      2. oranges*

        This book, yes.
        In a lot of ways, the strategies of leaving an abusive relationship in your personal life will be needed here. (Commit to leaving and enlist your support network to hold you accountable, expect to be love bombed, expect to be manipulated, be vigilant about your safety [even if you “don’t think he’d ever do something like that”], do not look back and BLOCK BLOCK BLOCK.)

        Good luck, LW. Run far and fast away from this job.

          1. UShoe*

            Holy moly, finally an explanation of my previous company and what made me stay for SO DAMN LONG.

          2. Dana Whittaker*

            O. M. G.

            Thank you for explaining five whole years of my life.

            This is revolutionary.

      4. emmelemm*

        Yes. Again, this book/author is not perfect, but it contains some absolute life-saving information. When you read it, if you’ve never thought about things this way before, it will open your eyes very, very wide. A lot of things that didn’t make sense will suddenly make sense.

      5. L'étrangere*

        Oh and don’t overlook ‘why does he do this’ by Lundy Bancroft. Less about stranger danger, excellent about manipulation by someone close. You want to really understand what’s going on here so you never get tangled into another variation again. Good luck LW, and please keep us updated!

      6. Salymander*

        Maybe check out Captain Awkward, too. Lots of good advice there for situations like this.

        And seriously? I was hearing screeching violins the whole time I read this letter. The CEO’s behavior is very, very concerning and I wouldn’t trust anything he has to say. CEO sounds like a cult leader. The HR person might have done the things she was fired for, but she may have just objected to something CEO did, or tried to set better boundaries. Maybe the CEO is trying to isolate OP from a potential support person. Unless OP knows for certain that HR person was actually toxic and did tell lies and start rumors and try to get OP fired, I would be really sceptical.

        1. wittyrepartee*

          Cult leader for like… the lamest cult. He’s not even the reincarnation of Pele or anything.

        2. Reluctant Mezzo*

          Maybe the CEO was jealous of any time the LW spent with her. And maybe the LW’s spouse needs to take precautions, too. No, I’m not kidding.

      8. No thanks*

        Maybe don’t give your money to a prominent AIDS denier who argues that survivors of domestic violence choose to be abused. If you truly think you may be in danger, there are quite a few resources out there written by survivors and experts to help you make a safety plan.

        1. wittyrepartee*

          Wait, he… denies AIDS? As someone who works in Disease Control, that’s friggin wild.

        2. Working Hypothesis*

          The book can still be a useful resource even if the author’s an asshole. Buying used is a good way to get the information while still avoiding giving your money to the author.

      9. Retrotardigrade*

        100%

        That “we’re so lucky” bit at the end absolutely screamed “forced teaming” to me.

    3. Popinki (she/her)*

      Yes, RUUUUUUUUUUUN!

      A) You don’t actually know why the woman from human resources was fired for. She might have been doing bad things, or she might have been telling him to back off of you.

      B) That’s classic abusive behavior, trying to make you think you depend on him, then taking steps to isolate you from your support network. He’s already driving a wedge between you and your husband.

      C) This is about the creepiest letter I’ve ever read on this site, and it started off creepy as fluff and got exponentially creepier as it went on.

      So RUUUUUN! And after you’re out of there block this whacko on social media, block his calls and emails, and be on the lookout for stalker type behaviors.

      And remember you’ve done nothing wrong, this isn’t normal, and you deserve to feel safe and respected at work.

      1. Puggles*

        Agreed. This is the most worrisome letters I’ve read on this sight. LW please follow Allison’s advice and do not tell him where you’re going, don’t connect w him on social media or anything like that. We are worried for your safety. Stay alert around him.

      2. Slow Gin Lizz*

        Point A is a really good one. He may also have been annoyed that she was around to provide another person for you to have a work relationship with. For all you know, *he* is the pathological liar and the one committing tax fraud (classic projection) and she was just calling him out on that.

        100% agree with everyone here: get out, OP, and stand your ground about not going on the trip that interferes with your ceremony. Maybe he’ll fire you for that, which would be SUCH a blessing.

        1. miss chevious*

          Or (and this is complete speculation) maybe the HR lady was the first “one he had been waiting for” and was pushed out when OP came along. I’ve seen this kind of fixated abuser “trade up” in personal relationships before, and suddenly, when the new person gets hooked, the original support is a liar or worse.

          None of this changes the advice: run, OP. RUN.

          1. Slow Gin Lizz*

            Oh yes, hadn’t thought of that before but you’re absolutely right, that could be the case. But yes, advice doesn’t change. GET OUT OP.

          2. GreenDoor*

            Came here to say the same thing. He was probably eyeing them both and figured the Admin was the better bet (typically paid less, not as much authority in the hierarchy = more depended on him) as opposed to an HR person (far more likely to have the ear of the HR Director, more likely to know how to use employment laws to stop his behavior/get him fired).

          3. Salymander*

            That is a really good point. I grew up in a fundamentalist christian sect that was really just a cult, so this was not all that unusual and I saw it happen a number of times. Abuser grooms and manipulates one person, but then a different one comes along that abuser prefers. Abuser then drops the first victim like a hot rock and swoops down on victim number 2. The people I saw who did this were all powerful men who had been grooming one woman but then decided to trade her in for a younger woman. A couple of times it was one man and a group who he dropped in favor of a new group. It was always the same basic scenario, though. The split from the original victim/s was always savage, cruel, and involved a lot of character assassination of the original victim/s and white knighting and displays of superiority from the abuser. It was brutal.

          4. Tara*

            Man. This letter gave me extreme anxiety. I was glad to see Allison mention that it’s very cult-like because that was exactly what I thought as I was reading it. I have no advice but I hope the letter writer can get away safely. This is terrible.

        2. Popinki (she/her)*

          I just had a “duh” moment as to why he’d want to get rid of the HR person:

          Because it’s not only isolating her from a work friend, this one was from HR, which would be the logical place for OP to start looking for help within the organization. Not to mention this HR person knew her and knew that she didn’t initate the relationship with Mr. Creepy. Now HE can go to HR and tell them that she seduced him, he’s innocent in all this, and it’ll be the CEO’s word vs a “lowly” assistant.

          She’s not lowly, nor is any other professional assistant, but Mr. Creepy obviously thinks of her that way.

      3. gmg22*

        Chiming in YEP on Point A. If LW only knows what happened with the HR generalist via the CEO’s version of events, that’s a red flag, because his behavior strongly suggests it might not be a trustworthy version of events.

        1. Salymander*

          Plus, CEO’s behavior toward the HR person shows what happens to people when CEO no longer has a use for them. He doesn’t just drop them, he drop kicks them, cuts off their contact with anyone in CEO’s orbit, and annihalates their reputation. I am really glad that the OP sees what a messed up situation this is, because many people are won over by this kind of intensity and fail to see how dysfunctional and abusive it is. If you don’t realize it is messed up, it comes as a horrible surprise when you are in past the point of escape or you are booted out of the circle and your life is torpedoed. Thank goodness OP knows this is terrible, and is just seeking confirmation that their instincts are correct and advice about how to handle that.

      4. Elizabeth West*

        All of this. ALL of it. And everything Alison said too.

        My eyebrows are in my hair now!

      5. Irish Teacher.*

        That very much occurred to me about the woman from human resources. I wondered if the LW had actually seen this behaviour – the human resources person lying about her, etc – or if the CEO had told her about it, because it seems odd that two people in this group would be engaging in very bizarre and quite different behaviour. Both have abusive/manipulative elements in different ways and yikes, if the LW does know for certain about both, she is very unlucky to have to deal with both.

        If she is just taking his word or the word around the company, I’d be concerned it could be another form of manipulation/way of gaining her full attention – “your other friend didn’t like you really. She was spreading lies about you. I’m the only one you can trust here.”

        1. Salymander*

          Exactly. Was CEO just trying to isolate OP? Was CEO done with HR person and gave her the boot while spreading lies about her? Who knows? It would be wise to view anything the CEO says or does with extreme scepticism.

      6. Phoenix*

        I had completely forgot about the earlier comments about the HR, focusing solely on that look at this combination

        “ occasionally felt that my boss did not approve of the amount of time that would get wasted while entertaining each other” aka, he didn’t approve of your relationship, especially with “ The CEO began to join our conversations”—aka, didn’t want you two (or just you) to have an independent relationship. This combined with “HR generalist was a pathological liar who was spreading horrible rumors, trying to get me fired” seems like it was more to break you two specifically up, WHILE possibly making himself a shoulder for you to cry on since your *great work friend he never trusted* betrayed you

        Also, where did you get this intel (tax fraud, pathological liar, rumors about you) from, from him, from others? Committing tax fraud is pretty serious and it could be he felt these ways because of the investigation going on prior. But if you have to work there while continuing to look for another job—try to see about making other friendships and how he reacts to those.

        1. Worldwalker*

          I don’t think the OP should work there while looking for another job — IMO, if this guy finds out that she’s looking, he could become physically dangerous. One of those work trips … “she came on to me” ….

          GET OUT! And while you’re preparing your escape plan, document document document.

      7. IndustriousLabRat*

        Agreed on all of this except one point:

        I think it may be wiser NOT to block his emails. Go ahead and send them to a “Creepy Ex Boss” folder, and generally disengage from them, but if this becomes a legitimate stalking situation- and I think the chances of that are non-zero – it is good to have a paper trail if you need to get legal help dealing with him in the future.

        1. Sarah M*

          +1,000,000! OP please please please document as much as possible! This is the kind of person who will 100% try to sabotage you once you *do* leave.

          I’m so sorry this is happening to you.

        2. Dasein9*

          Yes. And you can have someone else read the contents of the Creepy Ex Boss folder, too. You don’t have to put yourself through that.

        3. L'étrangere*

          Excellent point LabRat! In fact, if the LW can scrape up every email from the work account right now that may be helpful too, as it’s likely laced with toxic personal stuff. And start right now to keep a diary of interactions, with timing and topic of off-work blather (diary which you do not keep at work). Even if you don’t end up sharing it with the police, it should get you unemployment if your efforts to liberate yourself land you on the sidewalk prematurely

          1. Anita Brake*

            Agreed…keep all records of interactions and other CYA stuff at home, so that if he throws you out, you still have access to them at home.

            1. JessaB*

              Exactly, remember that he’s the boss, he can get IT to change things or delete things at will. You could end up locked out with no way to get to the paperwork.

              1. Marzipan Shepherdess*

                And – as retro as it may sound! – printing out material which could be blocked or wiped by IT and taking them home with you would be a good first step. After all, IT can’t block you from accessing a sheaf of papers in your own home filing cabinet!

                1. Migraine*

                  This is very smart, and probably less detectable than forwarding emails to a non-work account from a work account. Just make sure you have a reason to be printing out a lot of docs and make sure you collect them first.

        4. fleapot*

          In addition to the filter, I might suggest setting up an automatic forward to a trusted friend or family member.

          I’ve done this with an abusive family member; I’ve gone no-contact with him, but in the past he’s tried to stir things up in a way that actually did require my attention. Now, when this person emails me, it goes to a specified folder and is also forwarded to a friend that I trust to do triage. If he’s sending me (unwanted) birthday or holiday greetings, I don’t need to know about it. If he’s threatening something legal or financial, she’ll tell me about it so that I can protect myself.

          It would have to be a *really* trusted friend or relative, obviously, but it’s an arrangement that gives me peace of mind. (Also ensures that there’s documentation with a third party, which could be helpful if things escalate.)

          OP, I’m really sorry that you’re in this situation, and I hope you’re able to extract yourself safely.

      8. Petty Betty*

        Point A is so true. I was really side-eying all of the CEO’s relationship interference between the HR generalist and LW and then when I read the “reason” for HR’s dismissal, my eyebrows decided to take an impromptu vacation north of my hairline.

        The CEO seems very practiced at wedging himself between his targets, isolating potential victims, removing potential allies, and generally being an emotional vampire and sucking the life and soul out of a person.

      9. Mr. Shark*

        I tend to sometimes think that commenters over react to work situations on this site, even Alison, when they recommend quitting or give the advice to RUN.

        But in this case, I hole-heartedly agree. RUN. NOW.

        This guy sounds like he’s, frankly, obsessed with you. He’s taking all your time, cutting out your husband, got rid of the HR person who might’ve actually been on your side. He sounds abusive and stalker-ish to me, and honestly, I’m afraid for your safety.

        Quit now. Tell him you’re moving. Block his number, block him on social media. Don’t worry about getting a recommendation from him for your next job–you don’t want it.

      10. Nina Bee*

        Might be worth changing your address on your employee file and also check all your locks at home.. leaving may create worse behaviour. The boss sounds like they’re trying to start a cult! In ‘Conspirituality’ podcast episode 6 they talk about how cults use personal information for getting people sucked in and also using it to emotionally manipulate them later. Run run run

      1. Frank01*

        Absolutely the scariest! I hope to hear a positive follow-up from the OP… and soon. Even if she’s jobless, that’s more positive than staying with this cult leader.

    5. FrenchCusser*

      If you can POSSIBLY afford it, just don’t go back. Resign by email.

      Like, if you can pay your rent and live off of pasta and tuna until you find another job, just get out. NOW.

      Don’t answer his calls, don’t answer the door if he shows up at your house. I’m sincerely afraid for you.

      1. Crumbledore*

        I can’t stop thinking about how OP stopped and fast-forwarded in the middle of the post – this is only *part* of the story, and still we are unanimously horrified for them. I hope you are able to get far away from this CEO, OP, and quick. You don’t owe us an update, but I hope you’ll be comfortable sending one, because lots of folks are worried about you.

        1. SeluciaMD*

          Exactly! if this is how horrified we all are right now, what else could be lurking in that “fast forward” section? I’ve been in an unhealthy EA role with a person who relied on me far too much for personal stuff and it was toxic as hell. It was still nowhere near as creepy, scary and cringe-inducing as your story is OP.

          There is not one single thing in your letter that is normal or OK for this kind of professional relationship. Keep listening to the instinct that encouraged you to send this letter in the first place because it’s the one that is serving you well – it is telling you this is not normal and not OK. I know it can be really helpful to get external validation in these kinds of situations (if for no other reason than because the person causing you harm has worked VERY hard to make you doubt yourself, your “interpretation” of your experience, their “intentions”, etc.) but now you know: that instinct was right, everything about this situation is wrong, and there is no other option than to GET THE EFF OUT RIGHT NOW.

          If there is any chance you can quit without having another job lined up, this is one of the few circumstances where I’d strongly encourage you to do that. Even if it means eating ramen for a few weeks, I think your safety is absolutely worth it. This guy is dangerous and every minute you stay in this job is one more opportunity he has to hurt you – physically, mentally and/or emotionally.

          GET OUT GET OUT GET OUT GET OUUUUUUUUUT

          And please send an update when you have so we know you are OK! Sending you Jedi hugs and support and hope that very, very soon you will be free of this monster.

        2. Anita Brake*

          Good point Crumbledore! I had forgotten that part. Definitely get out, or don’t even go back if you can even possibly make that work.

      2. Worldwalker*

        The OP is married, which may provide some social/financial backup and make resigning by email possible. And with the employment environment right now, finding another job will be easier than it was a year ago.

        Again: There is nothing normal going on here. GET OUT NOW!

      3. OhNoYouDidn't*

        Agreed. Even make up some medical emergency that means you have to stop working immediately if you have to. But, if you can in any way afford it, quit immediately. This is super creepy and alarming.

    6. old curmudgeon*

      OP, I endorse what everyone else is saying to run like heck NOW-NOW-NOW and don’t look back, but I also urge you to check in with your state’s unemployment insurance agency. Some states in the US (the one I live in, for example) allow UI benefits to be paid if an employee quits with good cause attributable to the employer, and having a stalker boss grooming you this way would definitely fall under that heading.

      This may not be the case in your state, I realize, and interrupting one’s income (and potentially health insurance) abruptly can carry all manner of consequences, but please do yourself a favor and check into it. If you are fortunate enough to live in a state where that is true, you’d have at least a little income to keep things ticking over until you line up your next (better, healthier, nontoxic) job.

      Sending all manner of good wishes, and I hope very much that you escape safely and soon. We’d all love an update at some point if that feels safe, but only after you escape. Take care of yourself!

      1. Autumn*

        This is very good advice, If this is the case, find out what the burden of poof for this is, so that you can collect it. Also forget 2 weeks notice, when you pull the plug do everything you can do to disappear like a pebble in a pond

      2. B*

        Yes!! I have quit a job before, but it was for a specific reason, and I had documentation to back it up and I was approved for unemployment no problem (I’m in IL). This is worth exploring!

        1. MigraineMonth*

          This is very smart, and probably less detectable than forwarding emails to a non-work account from a work account. Just make sure you have a reason to be printing out a lot of docs and make sure you collect them first.

          1. MigraineMonth*

            Sorry, nesting fail. What I was going to say is that I worked for a company that was so notorious for constructive firings that you didn’t even need documentation to collect UI benefits.

      1. Nina Bee*

        what I thought too, sounds like their playbook although a lot of cults use personal information to gain control :(

    10. Worldwalker*

      This situation has more red flags than a Chinese flag factory.

      It resembles an abusive marriage to a disturbing extent — and like an abusive relationship, the greatest danger to you (and it’s possible that this may include physical danger) is when you leave. Be prepared for that. Be prepared for him to try to trash your reputation around the industry. Be prepared for him to go all ahead whackjob. But remember one thing: the longer you wait, the *worse* that will be — and it’s inevitable. The only way out of this job without him doing something like that would be if he got run over by a bus. It’s going to happen; just be prepared.

      This is one of the rare cases when you should quit with no other job to go to, because this guy is not normal, this job is not normal, this situation is not normal, and it’s only going to get worse from here. GET OUT NOW!

  2. Cube Farmer*

    Yiiiiikes. It sounds like even going to HR wouldn’t work, because it’s the CEO.

    I hope LW gets some support outside of work after all this goes down, because I wonder if that CEO is going to try and retaliate. Put up cameras around your house, put a dashcam in your car, etc.

    2. Azars*

      It almost reads like the CEO forced out the HR generalist for puffed up reasons, possibly because they were close to the OP.

      1. NoMoreOffice*

        Now I’m even more thoroughly creeped out. I hope OP is ok. This sounds like the back story from some stalker thriller.

        1. WillowSunstar*

          Me too. This sounds like the CEO has developed an unhealthy romantic interest (to a married person, no less!) Soap opera like, even.

          1. Elizabeth West*

            I’m not getting a romantic vibe; I could be wrong, but I’ve seen this kind of codependency in families where one must be loyal to a narcissistic parental figure who needs to control everything.

            Regardless, it’s super, super inappropriate and all kinds of nope.

            1. Wombats and Tequila*

              However, it doesn’t seem like a coincidence that it sounds like OP’s marriage is suffering. If I were OP’s spouse, I’d be over it–if nothing more than for the amount of time and energy this creep demands of her.

              OP, you should probably download and print anything you can so that the CEP can’t set you up for some trumped up legal charge. Maybe even consult a lawyer first. Not to scare you, but CYA.

      3. Jam on Toast*

        Yes!!! Who told the OP the HR generalist was a liar who was threatening her career? To me, that sounds like a total fabrication on the CEO’s part or trumped up charges that are so ‘fireable’ that it would justify their disappearance from the company. I think it’s much more likely that the HR generalist was derailing the CEO’s ability to monopolize the OP, much like an abuser increasingly isolates an intimate partner. “Don’t talk to your sister. She’s coming between us.” I can’t imagine living like this. It is absolutely frightening and I hope the OP can find the support and resources to get out as soon as they possibly can. Also, is she expected to use a company phone or other devices? Because if this individual is already so controlling, I would want to know if the OP’s technology is being monitored or tracked, by apps or other intrusive means, like a tracker, audio recorder or remote viewing of cameras, emails, messaging etc.

        1. knitcrazybooknut*

          I have lived like this. It is terrifying. But you can get out, OP. I had to draw on all my friendships, but I moved out in a day. You can do this, and you have this entire commentariat sending good thoughts your way. Take care of yourself.

        2. L'étrangere*

          Your local domestic abuse agency should be able to help diagnose such tracking on both a work and home phone. It wouldn’t be a bad idea to ‘forget’ the work phone at work outside of working hours, if there’s one

      5. Everything Bagel*

        I was wondering how an HR generalist commits tax fraud, unless that means in her personal taxes.

      6. Seeking Second Childhood, CTA*

        I honestly wonder if the HR generalist was not fired at all, but instead quit because he was doing this to her before.
        CEO would certainly want to prevent these two women talking if that’s the case.

      7. Irish Teacher.*

        Yup, “she’s telling lies about you. Don’t trust her. I’m the only one you can trust here” seems to fit the general pattern. That was my thought too and honestly, I’m not sure whether I hope I’m wrong or not. It’s even creepier if it is true, but if it’s not, the LW had to work with two unbalanced people who are, in different ways, targetting her.

      8. Cube Farmer*

        I hadn’t even considered this, but yeah, definitely could be the case and if so, double yikes!

    3. Observer*

      I hope LW gets some support outside of work after all this goes down, because I wonder if that CEO is going to try and retaliate. Put up cameras around your house, put a dashcam in your car, etc

      I think that it’s extremely likely that this boss will retaliate.

      2. Stinky Socks*

        Am I being ridiculous in thinking she should consider moving? 100% certain he knows her address.

        Sheesh, just reading that letter has me on edge and jumpy.

        1. paxfelis*

          If you’re being ridiculous for saying she should consider moving, I’m being ridiculous for thinking she should get a lawyer now. I wouldn’t be surprised if this boss tried to get everyone else to blackball OP so OP has to come crawling back.

        2. Mama Sarah*

          Maybe we’re all totally ridiculous? I thought getting a lawyer or a restraining order could be a good idea. Or get out of the country for a bit (or Hawaii!)?
          Maybe the boss isn’t totally over the top, but I wouldn’t chance it.

          1. Working Hypothesis*

            I think all of the above are good ideas, at least to consider. Moving takes time, and might not be necessary… but I would definitely get out of the area for a few weeks (go on vacation, stay with friends or family, etc) and set up security cameras before leaving the house. Email my resignation from wherever I already have left for, so that I’m not directly reachable when he sees it.

            Before they go back, they should check the cameras to see if anybody was there who shouldn’t have been while they were gone.

            Lawyer, definitely a good idea. Block on all social media and send all emails to a file where she doesn’t have to see them but where a trusted friend can check them to see if there’s anything dangerous in them. And apply for an order of protection if either the emails or the security cameras turn up anything alarming.

  3. Alexander Graham Yell*

    Oh, OP, this is so creepy and weird and just….I’m so glad you wrote in so you can see how completely not normal this is. Hoping we get an update from you that involves a new job ASAP.

    1. Pants*

      So so so with you. This is a Red Flag Factory. RUN!

      While Allison was comparing it to cult-mind (which it is), all I could think was that this is classic grooming behaviour.

  4. Littorally*

    My hair started standing straight up as soon as I read the title and it only got worse as I kept reading.

    Holy socks OP, get out now. This is the kind of thing that heads into “quit with nothing lined up” territory. And I would say, be prepared to take some defensive measures when you do — lock down your social media and have your spouse lock down theirs, etc. This guy is already tromping all over your boundaries and leaving will probably send that behavior to 11.

    1. EPLawyer*

      HEADS INTO? Yeah it already entered that territory and is half way through it (not attacking you, Littorally, just had the perfect line for this).

      QUIT NOW. Do not look back. Also once you have quit, BLOCK him, eveyrwhere. Social media, phone, zoom, whatever you had to do. He will not leave you alone just because you left. So be prepared to take steps, up to and including getting a protective order if he harrasses you.

      1. MsM*

        Yes. I sincerely hope he “confines” himself to a lot of guilt-tripping and/or threatening bad recommendations at worst when you submit your resignation, OP. But if he does escalate, you don’t need to treat this as a work disagreement: you can engage legal mechanisms to protect yourself.

    2. LadyByTheLake*

      Agree agree agree! If you can afford it, quit now even without anything lined up — if you can’t, it’s still a great market for executive assistants (and remote opportunities), so start applying today — now. And I agree with others that this guy is behaving so bizarrely that he may engage in stalkerish behavior when you leave so lock everything down.

    3. Keymaster of Gozer (she/her)*

      My best friend is an executive assistant of some 20+ years experience and once had a boss who started with the ‘you’re my emotional support!’ and gradually segued into ‘I own you so you have to let me into your house at any time/meet me in hotel rooms when I’ve had a fight with my wife/listen to me talk about every disturbing thought that enters my brain’

      She up and quit (which is rare to do on the spot in the UK) when he told her to do something absolutely inappropriate and basically said he’d wreck her career if she said no.

      1. Venus*

        I’m surprised that Alison only mentioned cult, and not that the CEO was interested in OP physically or at best an emotional affair. The whole thing screams of the CEO wanting a relationship with OP, same as your “meet me in hotel rooms when I’ve had a fight with my wife”. Not that cultish behavior can’t involve a physical relationship, and whatever thoughts are driving the CEO don’t really matter because all of it screams that the OP is going to be quitting soon, either because of Alison’s response or because the CEO says something absolutely inappropriate.

        1. Hills to Die On*

          That’s what it seemed to me – grooming OP for a relationship to get them away from their marriage.

          1. EPLawyer*

            The why doesn’t really matter. He is doing it. That’s all that matters.

            I don’t think it is sexual (only). By saying oh he wants a sexual relationship with her really triviliazes it. Well just remind him you are married, it will be fine. Or, full of yoruself aren’t you that of course every man wants you.

            Nope, this is about control pure and simple. WHY he wants control is irrelevant. OP needs to get out of his control. PERIOD.

            1. socks*

              I don’t think speculating about why he’s doing this is helpful, but I don’t think it’s trivializing to suggest he wants a sexual relationship. There’s nothing trivial about sexual harassment, and no one here is bringing up the possibility as a way to dismiss the LW’s concerns.

        2. bamcheeks*

          and not that the CEO was interested in OP physically or at best an emotional affair

          I suspect most people’s minds went there but I think it’s good that Alison didn’t say that, precisely because all of this is alarming enough on its own. We’re all kind of attuned to the dangers of sexual harassment, and sometimes that can mean alarming stuff slides under the radar because it’s clearly not sexual even though it’s still coercive and creepy af.

          1. quill*

            Yes. The context doesn’t need to be sexual or romantic for someone to be in an abusive relationship. Friendships and work relationships can be abusive too.

        3. Observer*

          Actually, that’s the first thing Alison said. She says “but a lot of it sounds like grooming, some of it sounds like the way cults brainwash people, and none of it sounds like a normal CEO/assistant relationship”, indicating two possibilities.

      2. Pants*

        I was a PA to a woman who decided I was her emotional support. I was a paid hostage and a poorly paid one at that.

    4. Hills to Die On*

      This is a case where you don’t need something lined up and maybe also okay to not give a 2-week notice. Just go.

      1. Really?*

        Agreed. Talk to your husband, clue him into what’s going on if he hasn’t already figured it out, and leave immediately for “personal reasons” and block him. Just reading this frightens me. If you need a reference, suggest you see if first boss will provide one, quietly. If you have prior jobs with good references, don’t use anyone in this company as a reference. This deeply disturbing.

      2. RabbitRabbit*

        Something lined up would be awesome because OP is NEVER getting a recommendation from this guy, ever, but that should still not be a hindrance to plans to GTFO. This guy scares me.

      1. publicsectorprincess*

        Document, document, document. Save all of the things(emails, texts, call logs) you possibly can. Keeping a diary might help in a few ways 1. keeping track of the overwhelming amount of inappropriate things & dates so you can be specific if requesting something like a restraining order 2. It will help you to realize how much is going on, and how valid your feeling around this are…I get the sense from your letter that just trying to summarize was reminding you of more & more issues.

        *And run as far and as fast from this as you can, as soon as you are able.

      1. Beany*

        Let’s not go overboard here. I’m thinking more The Hand the Rocks the Cradle/Single White Female/Pacific Heights/Fatal Attraction …

    2. OyHiOh*

      Mine too. It’s horrifying from start to finish, and I have a boss who can be bad at boundaries sometimes. On the plus side, related to my boss, they’ve recently started therapy and have said that boundaries is one of the things they’ll be working on. Personal growth and self awareness go a long way, as does the fact that my boss respects the hell out of my boundaries, even if they don’t always do it as well in return (I know way more about their multiple dating partners than I ever want or need to know. Just shut up already!).

  6. Alton Brown's Evil Twin*

    If the CEO paid you at going rates for a therapist, you’d be sitting on quite a nest egg. 3+ hours a day, every day, is absurd.

    This has nothing to do with his “emotional needs”, and everything to do with him trying to trap you into something.

    Get out.

    1. Southern Ladybug*

      I’d also say this is a situation where you do NOT give 2 weeks notice. When you resign – leave immediately.

      I hope you have other supports around you. And do not feel you need to protect this person. Factually state the expectations he had of you – he is the problem.

        1. Keeley Jones, The Independent Woman*

          Exactly. Send a resignation email and then immediately block any and all emails/phones/socials. Black hole this guy, make sure you have security cameras set up. There’s no such thing is going overboard in this situation.

          1. Venus*

            Depending on the CEO’s personality, there may be a benefit to automatically forwarding all his emails to someone OP trusts to keep them as documentation in case they are needed in future. Unfortunately it seems that all his comms are by calls that can’t be easily recorded, but in these cases documentation can be vital.

            OP: Strongly suggest that you make notes of as many of these situations as possible. Write down when they happened, and at minimum a vague description of inappropriate comments. Keep all emails that are inappropriate, and store them someplace outside of work. You likely won’t need this information, but if you do then it is valuable.

          2. Worldwalker*

            Yeah. This guy won’t *become* a stalker — he already *is* a stalker, but doesn’t have to act on it because he has the OP, by virtue of her job, always at hand. When he doesn’t, his stalking is going to escalate.

      2. Princesa*

        I would not show up again, send a resignation email, and block him from everything! It’s not like he’ll give OP a good recommendation anyway, even if she gives her two weeks. He’ll probably be too angry that she left. Also, OP, I hope everything goes well and that you stay safe :) so sorry that you’re dealing with a psycho like this.

        Is it rude to request an update letter whenever everything is said and done?

      3. Suzy Q*

        Yes, and when you quit, have your husband or another person waiting for you outside (this is, if you’re back in the office) so this creep can’t try to stop you from leaving.

        1. Cthulhu's Librarian*

          DO NOT QUIT IN PERSON.

          This boss is so firmly in the “socially acceptable to ghost” them territory, that I would argue for not quitting at all… just stop showing up, and block all their means of contacting you. However, since they’d probably start coming to your residence (or sending the cops) as a wellness check, you probably should resign – it gives you a bit of protection to be able to show the cops a document saying “no, he has no cause to ask you to visit me.”

          So, send a resignation letter via certified post, or courier, or email with read receipt – whatever you feel most comfortable with, and then NEVER go back near this guy. NEVER NEVER NEVER.

          OP, focus on your safety first. You ARE in danger, though you may not realize it yet. Do everything you can to keep yourself safe – and that means never being alone with this terrifying specimen of humanity again.

        2. Insert Clever Name Here*

          OMG absolutely do not quit in person. Quit by email. Any company property you have can be mailed to the office. And if you have not returned to the office and have personal belongings…I’d abandon them.

          1. ferrina*

            And when you quit by email, make sure to CC several other people (HR, COO and IT perhaps?). In your email, tell them what you are doing with the company property you have (i.e., you are sending your company laptop by certified mail to the office). Don’t ask, tell, and tell everything you need to in order for that email to be your last one.
            You don’t want the CEO claiming that you never quit and trying to reach out to you under some pretense of “well before you quit, you need to….” No. You just get to quit.
            He will 100% look for excuses to reach out to you. Do not engage, and if you think you might be roped back in, go no contact. Do not respond to him. If you respond to his 50th email, then he knows that he needs to email you 50 times to get a response out of you (I think Gift of Fear has something about this in the book?)

    2. Venomous Voice*

      I think you really need to document what you can with dates, save emails, take all your personal items home -say your going to clean them or bring in different things for a fresh new style or some BS in an effort not to trigger him-, and wipe any digital personal info. I would go so far as to try and make sure you delete any saved emails with personal info that’s not officially on file with the company. Then I would go to HR to report this, but quit then and there in the meeting with HR. This really sounds like it could quickly escalate into a dangerous stalker situation, so I would not even give notice. I would also talk to law enforcement to report your concerns. They probably can’t do anything just yet, but the paper trail could turn out to be critical if things get weirder.

      I would not even tell the CEO you are quitting or give notice, just take it to HR, but do it literally ON YOUR WAY OUT THE DOOR. And have your spouse or something else you trust waiting for you right outside the front door. This is creepy as hell, getoutgetoutgetout.

        1. starsaphire*

          LOL! I thought about that but I was afraid no one would get the quote if I changed it too much. :)

    5. Sylvan*

      They’re coming from inside the house, and a true crime documentary in a couple of years is going to open with a black-and-white photo of the house. I’m only half joking. Get outta there. Don’t travel with this guy.

    6. Jora Malli*

      You know that episode of Buffy the Vampire Slayer where the monster of the week dissolves into a whole swarm of bugs? That’s OP’s boss. He’s made entirely of bees.

    7. DrRat*

      Btw, letter writer, if you don’t get the reference, please go to Captain Awkward and search for “the house of evil bees.” It’s shorthand for “you’re in a horror movie, get out now.”

  9. Kiseki*

    This sounds like a horror movie… OMFG, get out! This CEO is sick in the head and exhibiting stalker like behaviour. You do not want to stay and find out what else they have planned for you.

    1. Yvette*

      It sounds like the kind of psychological thriller where soon the husband would start having car trouble and compain that the coffee from his favorite coffee shop tasted funny.
      In all seriousness, pleas listen to Alison and get out. Start quetly removing any personal effects you have at work, if you think he might notice replace them with things you don’t care about. “Oh, the cute mug with my cat’s picture? I took it home to give it a good bleaching and it broke.”
      Document all the crazy long phone calls, the business trips, the whole counselling thing and all the stuff you left out here. It may come in handy.

    2. The New Wanderer*

      I would watch that movie/read that book but oh my, OP, don’t live it! I think this is absolutely a quit-immediately situation, if you can get on your spouse’s insurance and live on one salary/savings for a bit. There are much healthier jobs out there for you, I hope you find one ASAP.

  10. Audrey Puffins*

    OP, you knew the answer before you even finished writing the letter, and yes, we’re all going to confirm it for you. This is not normal. Get out. Take care of yourself.

    1. Hare under the moon with a silver spoon*

      + 1
      Jedi hugs to you OP from London, know the whole AAM community is behind you.

  11. MishenNikara*

    “(in fact, consider saying you’re moving out of the area)”

    Hell, considering your address is gonna be on file and he’s the CEO you might even make this a reality.

    Run.

    1. KoiFeeder*

      If it’s feasible to move to an area that’s inconvenient for him to access, I’d strongly advise going that far, although I know that’s going to depend on your financial situation and you/your spouse’s ability to find a job in such an area. But this is a horror movie, and you need to Get Out.

    2. Collarbone High*

      A potential way to avoid that problem: rent a mailbox at a place like Mailboxes Etc. They give you an actual street address (not a PO Box) that the LW could submit to HR/payroll as a change of address and the place to send any final documents. That would remove the LW’s actual address from their files and reduce the chances of the CEO getting it by asking someone.

      1. Working Hypothesis*

        Assuming that the obsessive CEO isn’t already keeping all of LW’s information in a private shrine or something, apart from the regular files.

  12. WomEngineer*

    Even if he wasn’t CEO, it wouldn’t be acceptable for any manager (or coworker!) to treat OP this way. It’s so… invasive. The power imbalance makes it all that worse.

    1. Lily Rowan*

      Yeah, I once had a boss (a mid-level manager) who liked for me to sit in her office while she worked for no good reason, and that was bad enough! She found my presence soothing.

      1. DivineMissL*

        Ok, Lily Rowan, this is really creepy too. She was taking you away from your regular duties to…sit there? While she worked?

        1. JLP*

          Body doubling is a valid way of getting things done for folks with ADHD (and possibly others). Basically, ask a friend to come over and hang out while you clean. The friend does nothing but sit there. From a work perspective, there are various virtual spaces where folks hop on a call together, all go on mute, and work.

          Not saying that’s what Lily Rowan’s boss was doing; just offering a potential reason that is less creepy – still a waste of company resources but less creepy.

          1. Lily Rowan*

            Yeah, at the time I figured, if that was her assignment for me, OK, sure. From various other observations, I would say she was likely not neurotypical, so yeah, it was genuinely helpful for her, but still weird for me.

          2. pancakes*

            It’s pretty creepy to treat someone as a prop or “body double” without even telling them what’s going on, let alone getting their consent, even if it does help one person concentrate. People who meet up online for that purpose are clear about what they’re doing. Someone told to sit in a room for no particular reason is not.

          3. Pay No Attention To The Man Behind The Curtain*

            I think this might be what my grand boss is doing virtually these days. She’ll call my boss on Teams to a video “meeting” but it’s her just working through her thoughts and spreadsheets out loud with him as witness. There’s no input or task for him but to sit and listen.

          4. Mallory Janis Ian*

            I’m hearing about body doubling just now for the first time, but in retrospect I’ve done it.

            First there was a neuro atypical person in my womens group who said she was having trouble focusing on and completing her taxes. She was finishing her PhD in physics and was basically exhausted with anxiety. I asked if it would help if I came over and sat with her while she did the taxes just to provide some moral support, and she said it would. She didn’t really need any help with it, she just kind of talked herself through the 1040EZ with me sitting there and chiming in minimally.

            Also my daughter is helped by me just sitting with her while she completes paperwork that would otherwise stress her the heck out. She has anxiety and it spikes through the roof over simple routine forms (ie. 1040EZ, the housing form for college dorms, etc. Like, forms that just ask for basic information that one knows about oneself, but it’s stressful to encounter it in a paperwork intake format). It’s blowing my mind that this is a named thing; I just thought I’d encountered a couple of people who were helped by a calming presence while they did something that’s stressful to them but that doesn’t bother me.

            1. I take tea*

              Oh. I always prefer to have company while doing some stressful things, because it helps me to focus to get things done and not get overly anxious. I did not know that was a thing, I just figured I’m bad at adulting. I learn such a lot from this space!

              To OP: adding to the chorus of “no, not normal and please get out as soon s you can”.

              1. JESUS IS THE MAN!*

                I just learned this too! High five!

                I am *much* more likely to put away my clean laundry if my spouse is sitting there for moral support.

    1. Emotional support capybara*

      This this this this. If ever there was a Real Winners Quit situation this is it get out get out get ooooouuuuut.

        1. SloanGhost*

          Actually this is a GREAT point. OP should consider getting all their financial/tax/whatever docs on the DL and then they should just peace out WITHOUT giving notice.

  14. Snarkus Aurelius*

    Your boss asked for a: wife, assistant, therapist, nurse, consultant, 24 hour crisis line, and best friend.

    You are only one of those things. You shouldn’t be anything else. It’s unhealthy and unprofessional.

    To quote the EA in my office, “My goal is to get as much done for Boss so I can see and hear as little from him as possible and never on a weekend.” (Boss is horrible.)

    1. drpuma*

      I love your Boss’s EA’s stated goals and think they are job goals for most of us! OP, this awesome EA has the right idea and hopefully shows you a real-life example of how far out of whack your CEO’s expectations are.

    2. Liz*

      Heck, I’m an EA to a boss I genuinely like and enjoy working for, and those are still my professional goals.

  15. fposte*

    To be even more emphatic about what Alison was addressing in the last comment: you do not need his consent to leave this job. Assume you will not get it and that you will leave without it.

    2. Anonym*

      And don’t worry about reference from him. There is no reference to be had. He would likely only use it as an attempt to manipulate your life. There is no bridge to save (or burn). Please get out ASAP. This situation is scaring a lot of us here for you.

      1. ferrina*

        This. He may try to claim that he’ll give you a good reference if you only just [SOMETHING]……but that will be an ever shifting goal post that you will never be able to attain. Even if he claims you can use him as a reference, be prepared for him to undermine you every step of the way. His only goal is to keep you there, by any means necessary. If that’s by leading you on about a reference, he’ll do that.

      2. Jora Malli*

        If you use him as a reference, I’m 99.9999999% certain he will badmouth you to everyone who asks in an attempt to ruin your chances at working for anyone but him. Do not give his contact information to any potential employers.

      3. Snakebite*

        For real! Any bridges just give the CEO access to you, which jeapordizes your safety, OP. Just remove yourself without being in person and keep your safety and that of your family as the number one priority. I would caution against communicating with anyone still working there for a while even. I really hope this all just a distant memory for you very soon!

    3. Slow Gin Lizz*

      Yes! “No” is a full sentence. So is, “I quit.” Neither one deserves any further explanation.

    4. Working Hypothesis*

      You also, in this situation, should not give standard two weeks’ notice. That’s two weeks in which he can work on ways to manipulate you into staying, and some of that manipulation can get outright scary. Don’t put yourself in that position, LW. Nobody HAS to give notice, at least not if you’re in the United States (even elsewhere, IIRC the worst you can incur is a financial penalty and it would probably be worth it) and you could be in real danger if he escalates out of panic at the thought of losing you.

      Change your address of record (somebody else described how to get a real-looking address via a mailbox), quietly, without telling anybody why. Then take your things home from the office when he doesn’t see you doing it, send an email to HR (NOT to the obsessive boss!!) announcing your resignation effective immediately, and don’t go in again even once.

      You should also write down the WHOLE story you didn’t have space to tell us, with as many details and specifics as you can remember (dates, places, and *exactly* what happened) so that, if he starts to stalk you, you’re prepared to ask the courts for an order of protection. And block him on every form of device and social media account you have.

      I know we all probably sound pretty dramatic, LW; but please trust us — this situation, just from what you’ve told us so far, really is that extreme!!! This man is so obsessive about you as to be truly dangerous and you need to get away from him NOW, and protect yourself and your family.

      Please, please give us an update after you’ve left. I hope all goes well for you.

      1. ferrina*

        Yes, do all of this!

        Writing it down is so, so helpful for when he gaslights you and everyone around you- you know the truth before he started burying it. Giving same day notice is essential- I’ve done the long goodbye with someone who exhibited similar behavior, and it’s an awful process. It started with guilting (“It’s so hurtful to me that you would do this! And without letting me know in advance- I trust you!”) love bombing (compliments, gifts), future faking (making promises that he would keep for a couple weeks, maybe a month, but would never truly come through- look for a promise of a raise or different responsibilities or “I won’t ask you to do X again”), then telling me how scary the world would be and how I would never be accepted (which I blocked out at the time but still creeps up in my psyche on bad days), then threats (never anything I could take to the police, more showing up places with vague excuses so I knew he could always find me, making vague comments about how I’d regret leaving)

      2. Mama Llama Drama*

        I wonder if something can be turned into the police/courts (or maybe some sort of agency/watchdog group/association or local news or something) now in order to prevent anyone else being hired by this creepy person. LW, your first priority is yourself – get out and get safe. Once that’s done, if there’s any way to shut it down so that this creep doesn’t ever hire another “assistant”.

      3. LMB*

        We all sound dramatic because this letter is truly scary. Everyone has made really good points about documenting things and taking precautions but I’m really worried that won’t be enough. This guy is not going to react well to loosing her.

        1. Working Hypothesis*

          Leaving is always the most dangerous stage of an abusive relationship, but all you can do is prepare as well as possible and then stay well surrounded by safe people and in as secure a location as you can. There have been some really good suggestions made about how to do those things. It’s not completely risk-free… but it’s a lot more dangerous to stay, because eventually they’ll *still* have to leave and meantime they’ll be risking all the continued abuse of staying in this guy’s power, too.

          I really hope we get an update that says “I’m out of that job and safe, and he hasn’t been bothering me / doesn’t know where to find me now,” though. I’m going to be worried about this LW’s safety till we hear how the departure process went.

  16. HannahS*

    This sounds really frightening. This guy wants to possess you. I don’t mean in a supernatural way, but he wants you to be *his* in an intensely creepy, unhealthy way. I don’t know if he also wants to sleep with you or hurt you or rescue you and have you adore him forever but something intensely weird is happening. Your instincts are correct. Get out.

    Look for a new job. Do not tell him you are doing so. Once you find a new job, cut all connection from him.

    1. Morticia(she/her)*

      I think this might be a case where the LW shouldn’t wait that long. Leave first, get the job after. Document any weirdness you have access to (emails, phone logs), and cut and run. Also, and this might be weird in a work context, but this is a weird work context, recommended reading would definitely be Lundy Bancroft’s Why Does He Do That.

      1. HannahS*

        Yes, that’s fair. If the OP can afford to leave without another job lined up, she should consider it.

  17. CatCat*

    100% get out. Clear anything you have from the office before you give notice if you still have anything there and download anything you may need (HR records, pay stubs, work samples). He may flip out and dismiss you immediately (might be a GOOD thing in this instance so you can then go ahead and block him).

    I’d still give two weeks notice if he doesn’t have a reputation of letting people go immediately, but if he does anything inappropriate/creepy during that notice period, nip it in the bud and go. “Two weeks notice was a courtesy. However, [X thing he just did/said/is trying get you to do] is not professionally appropriate. Therefore, I am leaving my position effective immediately.” And GO.

    1. CatCat*

      I’ll add that two weeks notice are for your benefit, not his. So you can honestly say you gave two weeks notice if it ever comes up. But the moment he steps out of line (and I bet he WILL), get out.

    2. Daisy*

      I would ask and get approved for two weeks vacation before giving two weeks notice at the very end of the last day. Because I wouldn’t feel safe being there two weeks.

      2. Working Hypothesis*

        I might try that, but frankly that’s the ONLY way I would be giving any notice in this situation. Yes, better for LW to have given it than not, in looking at future jobs… but better that she do without than that she put herself in his sphere of control for even one more day after she’s let him know that she’s leaving. That’s likely to trigger a massive meltdown and quite possibly a dangerous one.

      3. Mama Llama*

        Or ask and take your vacation (i’d be surprised if he would even approve of the time off) and give your notice before you come back or even mid vacation. But either way just cut it off fast and do it over email.

    3. The Hippest Underground Marching Band in Brooklyn*

      This situation sounds terrifying. Please consider quitting without notice, (after having cleared out your things, downloaded your HR documents and work samples, etc., as others have suggested.). The behaviors the CEO is exhibiting sound a lot like the behaviors of abusers in personal relationships. The most dangerous time for someone who’s the target of that kind of abuse can be when they’re trying to leave the relationship.

    4. sara*

      I would definitely not give notice, or would give notice but either WFH for the notice period or be on vacation for the notice period. I think not being in the same place with this person after giving notice is very key. Or having a plan for that to be possible. Just major unsafe vibes happening here.

  18. Amber Rose*

    My skin started crawling a quarter of the way through this letter and now I just have a litany of NONONONONO going on in my head. This is so creepy and weird and wrong and NOT OK and just…

    OP, get the heck out of there. Dude sounds like the type of guy who stars in horror movies called Psycho or Skin Suit or something. D:

  19. grubsinmygarden*

    OP, after you hopefully leave, please change your phone number if the CEO was calling you on your personal phone.

    1. Ama*

      Yes, go ahead and get a new number now and start transitioning all of the contacts you want to keep to that number (and do not give it to any coworkers). CEO sounds like the kind of person who will figure out you’ve blocked him/got a new number and coerce one of your coworkers into calling you and then take over the call.

      I am not normally this paranoid but this guy’s behavior is so far beyond normal that you should take all precautions to completely cut him off once you leave.

      1. Keeley Jones, The Independent Woman*

        New email too. I know changing emails and phone numbers can be a major hassle, but this is the rare instance it’s necessary.

        2. quill*

          And if possible, do NOT allow social media profiles / old contact lists to associate themselves with your phone, as it is possible for people to get your phone number from two factor ID out of a social media service, especially if they pay someone. (I would consider wiping your facebook out and starting fresh with that new email. Or if you don’t use facebook anymore, just wiping it out point blank.)

      2. MsM*

        And make sure everyone you give the new number to is a) told that you’re keeping it confidential for safety reasons, and b) is someone you can trust to respect that.

      3. L'étrangere*

        Better to get a new phone and number, and carefully filter the ail, so evidence is preserved. I agree that he’s likely to be enraged by her departure, and having a record could be very helpful

  20. Oxford Common Sense*

    Run don’t walk. This isn’t normal and you don’t deserve it. And absolutely be prepared for backlash. Wishing you all the best! Please let us know how this progresses.

  21. Excel Jedi*

    This dude thinks he’s Tony Stark, and you’re Pepper Potts. Next he’s going to get you a 10 foot stuffed bunny.

    That’s not how the real world works. At all. As Alison said, RUN.

    1. Teekanne aus Schokolade*

      OH MY GOSH YES!!! This is the exact analogy! I’m sure that’s what he’s thinking, and even their relationship was so freaking off. (Pepper having to kick his sexcapade partners out of his bed every morning after he’d abandoned them for example). I don’t want to make OP paranoid, but they should consider ways he might already be monitoring them and consider preparing the means for a restraining order in case their boss flips out.

      1. quill*

        It is not cute, #relationship goals, or healthy to be the only thing keeping Arrogant Rich Guy (or Arrogant Smart Guy, etc,) afloat as a functioning adult. No matter what kind of super suit he’s built.

  22. Antilles*

    “Eventually there was a huge blow-up when it was discovered that the HR generalist was a pathological liar who was spreading horrible rumors, trying to get me fired, and committing tax fraud. She was let go.”
    I really wonder about this. I’m guessing OP heard this from the CEO and if so, I don’t believe a word of this.
    In light of everything else in the letter, this almost strikes me as the way that abusers try to separate people from their support network – you shouldn’t stay friends with Generalist, she’s terrible, you can’t trust her, you can only trust me…

    2. Amber Rose*

      Compare and contrast with the earlier statement: “I occasionally felt that my boss did not approve of the amount of time that would get wasted while entertaining each other.”

      Suspicious as heck.

    4. Yvette*

      Excellant point, any way to confirm it or to reach out to her? Because abusers tryu to separate dtheir victims from any support, emotional or otherwise. CEO is already interfering with the LW and husband’s relationship.

      2. Slow Gin Lizz*

        Good point, Yvette. OP, if you have any contact info for her, see if she’d be willing to give you her side of the story. As long as you feel safe doing so, of course.

    5. MsM*

      To be fair, I would not be entirely surprised if toxic CEO also attracts other toxic employees. Including people who turn even more toxic when they realize he’s got a new favorite.

    6. Azars*

      Yup, I thought so too! They’re friendly with the OP and suddenly get fired for being a pathological liar who’s trying to get the OP fired? It read to me like clearing away the OP’s support network and removing an easy line of communication to HR.

    7. BigHairNoHeart*

      I’m guessing that either this story about the HR person is fake and was concocted by the CEO to isolate the OP or that it really happened, and the CEO used it to their advantage (talking about it to OP at length and possibly exaggerating details, etc.) to isolate the OP. So, the result is the same regardless of the intention.

    8. Putting the Dys in Dysfunction*

      OP, this very possibility should encourage a course of action you should already considering before you leave: document the obsession. Emails that show the abuse and the control, and other relevant digital or hard copy material you can lawfully take with you.

      This CEO might not stop with a bad reference, but might try to fabricate some kind of bogus allegation of *your* (supposed) illegal behavior, either as a means of maintaining control over you or in retaliation. If you have documented evidence of the CEO’s horrific treatment of you that will go a long way in either preventing or defending against such actions.

      Another suggestion: consult an employment attorney ASAP. A few hundred bucks spent on a consultation now may save you lots of heartache and money in the future.

    9. This sounds familiar. . .*

      I find it interesting that she mentioned “trying to get me fired”. That sounds like his way of insuring a clean break between the two without her talking to this person again.

      2. Worldwalker*

        Yes.

        And if that’s what the CEO wants, that’s a very good reason to do the exact opposite. Locate the ex-HR person and hear her side of events.

    10. quill*

      Also, personal experience? “She’s trying to sabotage your career” sounds an awful lot like “she’s mocking you behind your back,” which was one of the wedges between me and all my school friends when I was in an abusive friendship. The abrupt nature of the “reveal” and the adding in something personal to the OP to an already overwhelmingly varied list of badness certainly seems like the CEO might as well be saying that OP’s judgement is flawed, she ‘needs’ him to ‘mentor’ her and keep her safe.

    11. hbc*

      Oh, my bet is that she was spreading something around, and that it was horrifying. As in, “CEO is being really inappropriate with OP, and it’s really hard to watch” and “I’m not sure if it’s mutual, but I’ve never seen an EA travel with their executive half so much and *not* having a sexual relationship revealed eventually.” Sometimes truth is the nastiest gossip of all.

      And I wouldn’t be at all surprised if the tax fraud having something to do with inappropriate business expenses, perhaps unknowingly putting things through for the CEO and then getting thrown under the bus.

  24. Smithy*

    First run.

    Second, run like this is highly abnormal. While it’s very possible that the HR generalist who was let go was engaged in tax fraud and problematic behavior due to what’s likely a problematic workplace where other’s have room or lack of guidance to engage in their own problematic behavior – it’s also very possible that the HR generalist was targeted to appear problematic on their way out. Maybe they were 100% responsible for the tax fraud, but maybe they just followed bad guidance or were part of a larger group making that decision. Or they had nothing to do with it, but became an easy target when they were targeted to leave.

    If you have work equipment – make sure it’s not only ready to return but completely cleared of any personal information, materials, saved passwords, history, etc. Particularly if you have a work phone where the mix between work and personal use would have been normal or perhaps even encouraged. If there are digital chats or emails that indicate the most problematic of behaviors – screen shot them, save them on your own devices before giving notice. If there are any workplace policies or guidelines that you signed, make sure you have copies of those at home. Clear out any personal effects from the office before giving notice and do so in a subtle way. When you give notice, have nothing left if in the office you wouldn’t mind losing.

    Basically, truly assume the absolute worst.

  25. Trek*

    One of the hardest things I had to learn without being told as a leader is that I am no longer ‘one of the team’ and I cannot just hang out with them even if we get a long well. My team needs their space even at work, they need time to collect their thoughts and not sensor themselves, they need to not have me or our company as their main focus all the time.
    Your CEO has to know this by now but he is violating so many lines that it’s bazaar. I don’t know if HR could help in this situation-use your best judgement. I would loop them in once you plan to give your notice as you are worried about retaliation or at least more bazaar behavior. Bottom line you need to leave ASAP, even without a job lined up if possible but I understand it rarely is possible.
    I’m curious when his behavior crosses the lines on harassment and/or hostile work environment. I would consult someone on that with the additional details/experiences and see if they can offer advice/solution.

    1. UKDancer*

      Yeah this hit me when I moved to a management job. I’m not part of the team, I don’t get to go to the informal pub sessions. I need to give them space without me so they can relax.

      I socialise informally with the other managers who are at the same level and have built my network out that way.

    2. WellRed*

      I feel like he crossed the line way back in 2019 when he, the CEO! Started joining them for smoke breaks.

        1. JustaTech*

          Yes, this! Once, once I (a committed non-smoker) joined a coworker (peer) on her smoke break. The weather was lovely, the wind blew the smoke away from me, but it was still weird (as a non-smoker) and she never invited me again.

          Maybe it’s more normal for folks who grew up with smokers/ smoking in public, or in an area where smoking is very common, but this is very much a “weird/off/ trying too hard” flag. (It’s tiny compared to the neon sign of all the CEO’s other behavior, but it establishes a pattern going way back.)

          Also, when is the CEO getting any work done? Commentariat, would there be any value to the OP reporting the CEO’s non-work to the board on their way out? (Probably not.)

          1. quill*

            There are enough businesses where the CEO is just an overpaid walking signature that I don’t think it would help.

          2. L'étrangere*

            Don’t be so weird about the smokers. I once worked at a very unfriendly place where it turned out the few nice people were smokers. Did I make it a habit to stand outside (upwind) with them? You bet, that was the only time we had to ourselves. They laughed about it a bit, but nobody minded

            1. Middle of HR*

              Yeah I made friends in college this way, as non smoker. But I made a point to find something else to do if people seemed not to want company, and also I was, y’know, a classmate who already knew these folks a bit, not like the Dean of the college trying to chill.

    3. Observer*

      One of the hardest things I had to learn without being told as a leader is that I am no longer ‘one of the team’ and I cannot just hang out with them even if we get a long well.

      This applies to his joining the chats. But the rest? That’s so far out of normal behavior that no one needs to “learn” about it.

    4. WantonSeedStitch*

      Yeah, I was promoted from an individual contributor role into a management role where my direct reports were my former peers. We had a great relationship, and often hung out together when we were at conferences. But when I became a manager, I remember needing to be conscientious about chatting with them for a bit at a conference reception and then saying, “well, I’m going to head over to see [folks I knew from another organization]. You guys have a great evening!” I didn’t think they should have to deal with having their manager around while they were trying to unwind and have fun, even if we did like one another!

    5. Another_scientist*

      I thought that Alison did such a good job capturing where there are moments of appropriate emotional support between an exec and a support staff. Sometimes the exec is dizzy with deadlines and is blind to an obvious option to postpone or delegate something. Sometimes I can sense uneasiness or reluctance about a project, and I can tease out what’s the matter and that leads to a resolution. Or sometimes we cheer together for a big milestone or I just say “well done with that big presentation”. Execs are people too. People skills are important to achieve good work.
      But OP’s CEO is in a different dimension! Red flags everywhere.

  26. Mehitabel*

    LW – please please please, for your own health and safety, get out of there. Now. And don’t bother giving notice, because trust me, the guy will make your life unbearable if you try to keep working once you’ve told him you’re leaving. Don’t be alone with him when you tell him, either. Either quit in writing, or have your spouse with you, or something, because this guy is unhinged.

    And be prepared just in case the guy goes into stalker mode because that is absolutely within the realm of possibility. Block him on your phone, email and social media and do some research on other measures you can take to protect yourself. I’m not saying he will turn into a stalker, but I am saying that he might. Be prepared.

    1. AllTheBirds*

      Agree 100%. Can your spouse accompany you to the office as you walk out for the last time?

      2. I am The Lola*

        Take your partner, your dad, your partners best friend, the local football team and any sumo wrestlers or bouncers you might know. Let him know you are THAT protected and the only one who will get hurt if he comes after you is him! Please update us, because I promise, even though we don’t ‘know’ you, every last one of us is concerned for your welfare!!!!

          1. AllTheBirds*

            Yeah, I take back my suggestion… it would NOT be safe to go into the office (ever again, though I realize it might not be feasible for OP for reasons).

            1. Working Hypothesis*

              Yup. No need to go in again. Quietly change the address of record on file with HR (there’s advice on how to do this on one of the content threads above). Equally quietly, bring your personal things home from the office, including wiping any personal data off any computers that belong to the company. Then leave for the last time.

              AFTER all that, send a letter to HR (not to the CEO boss) resigning effective immediately. Don’t give a reason, but do make it clear that the decision is final and you don’t wish to hear from the company again except to have your last paycheck mailed to your address on file (which, by this point, should be a normal-looking street address which is actually a mailbox at a mailbox company).

              Block your boss and all other company members (in case he pressures them to get in touch with you on his behalf, or to let him use their phones or accounts to reach you), and stay clear of that area of town for several weeks at least, especially if you’re not accompanied.

              Also, make sure you keep written records (even if it’s just writing down all the facts you remember — doesn’t require external evidence, though keep that too if you happen to have any) of everything you recall that you would have put in this email to Alison if you had had unlimited space to write it in. You might need those documents to justify later action… an order of protection if you need it, or supporting evidence if your boss tries to deny you unemployment coverage. You are leaving voluntarily, but given the circumstances you might be able to get unemployment anyhow, because leaving due to horrific circumstances is often considered constructive dismissal.

        2. quill*

          Also if you have a large and not obviously friendly dog, a friend who is a veteran (preferably a male friend, because that’s going to make a bigger impression on this CEO) or a friend who is a cop, firefighter, or any other profession known for toughness.

          Creepy men are most easily run off by large numbers of other men they assume can take them in a fight.

          Though this only applies if you absolutely have to go there. If you don’t? Stay the heck away and write off your office cardigan as collateral damage.

      3. Dinwar*

        Marines are pretty good for this sort of thing as well. A few friends of the family went into the Marines, and during some rough times my sisters were able to ask them to accompany them. It’s hard to act big and intimidating when there’s someone who just came back from an actual war zone in the room. The ones I’ve met at work (a surprising number go into field geology) look for opportunities to help people in distress, so I’m pretty confident this is a consistent thing in the Corps.

        Police are another good option. An off-duty cop airing out the uniform or trying on a new vest tends to forestall aggression. And pretty much everyone knows that police take a very dim view of harassing or harming an officer, on duty or off.

        Though honestly, this is pretty much a last-resort sort of thing. You’re preparing for combat at that point and it’s not unlikely that the CEO will respond in kind. The better option is to preclude conflict totally–block the CEO, send everything via courier or ship it back in some way you can track, and include your resignation letter. If you can bear to part with them, leave the stuff in the office and chalk it up to yet one more thing the CEO took from you.

        1. pancakes*

          Why not make your third paragraph the first? It really isn’t a good option to plan on having a physical showdown with this guy. Speculating about whether marines or cops would be better company is beside the point.

          1. Dinwar*

            I have some experience with this which may be useful should the LW decide to go this route. I don’t advocate for it, but it’s the LW’s decision. I’m a consultant; ultimately it’s my job to tell clients “If you do X, here are the possible ways to do it and the potential problems from each, tell me which way you want to go.”

            Second, I understand the desire to fantasize about what one would do in these situations. Once you realize you’ve been violated in some way (and abuse is a violation) some people react rather violently, at least in their minds. It’s normal human behavior–not particularly helpful, but normal. I’m making more of a conscious effort to not condemn normal behavior. It’s part of what’s wrong with social media, and with society at large, and I’m trying to do my small part to reverse this trend.

            Third, a common writing style/rhetorical tactic is to put the most important thing at the end, since that’s what most people remember (or at the beginning, for the same reason). Usually it’s seen with longer works than a comment to a blog post, but it’s definitely a common style. It’s one I tend to favor.

            1. pancakes*

              Ok, but you’re a commenter here like the rest of us, not a consultant, and there is no reason to believe the letter writer or any other person you know nothing about has burly, uniformed friends or family waiting in the wings to physically defend them. And I don’t like the implication that those of us who haven’t “been violated in some way” need to just look the other way when people who have are talking about violent fantasies on account of that being normal. Normally people don’t mistake those fantasies for actionable advice. “Normal” also doesn’t mean “needs to be continuously normalized at every conversational opportunity.”

              I think you have taken my remark about making your third paragraph the first very literally. I was trying to politely say it doesn’t need to be there at all because as you yourself acknowledge, it isn’t advisable for the letter writer to plan on having a showdown or “combat” with this dude. To the contrary, that would probably be a needless risk.

      4. Archivist*

        I had a situation where my husband had to accompany me to the office at 6 am to hand in my resignation letter (leave it on a prominent spot-I didn’t resign in person). If you don’t have a spouse or boyfriend have a friend that looks intimidating accompany you. I recommend writing a list of personal items at the office. Also, unfollow and block him on linkedin.

    2. Dramatic Intent To Flounce*

      Yes. Block him everywhere, and document EVERYTHING you can. Expect that when you leave there might be an extinction burst where the bad behavior intensifies. Don’t let that stop you from getting the hell out of dodge, just make plans to address that. (It actually might not be a bad idea to have all his emails be dumped directly into a Potential Evidence folder, where you don’t see them but if things do escalate you or a trusted third party who has nothing to do with this job can look through them and decide if it’s progressed to ‘active threat.’ Do NOT reply to those emails, regardless. He will want to know he’s getting under your skin with those, and to get your attention even if it’s negative. Discuss them with a therapist if you need to. If you’re not seeing a therapist right now, that should be a priority right below ‘GET OUT GET OUT GET OUT.’)

      I’m not advocating ‘file a restraining order’, because even if you get one that still means having to see this creep in court. Best case scenario for you is you lock him out of your life and he eventually stops trying to harass and creep on you. But prepare for the fact that this behavior is so WILDLY dysfunctional – professionally, socially, on EVERY level – that it will likely get worse when you get out, and give yourself some contingency plans for that. What do you do if he keeps trying to get through your blocks? If he tries to accost you in person? At what point would his escalation make it worth the risks to involve law enforcement or take legal action? Hopefully none of that contingency planning will be necessary, but better to have those ahead of time and not need them than have to decide when you’re already freaked out.

      And seriously, if you’re not in therapy already, prioritize that. If you are and haven’t told them about this, do so. If your spouse doesn’t know just how bad things have gotten, tell them – you want the people you trust most in your life in your camp, as horrified by this as we internet strangers are and helping you figure out how to get the hell away from this CEO and get back to having a creep-free life. This is not your fault. This is squarely on the CEO – Allison was right to compare tactics here to grooming and cult recruiting. Anyone who hears this and thinks it reflects badly on you rather than him is telling you something important about themselves.

      GET OUT OF THERE.

      1. pancakes*

        That is not entirely correct in my state with regard to restraining orders. A partial excerpt from NY Family Court FAQs:

        “When you arrive at court, notify a court officer in the part (room) where your case is being heard that you are afraid to see the respondent. The officer can arrange for you to stay in a place away from the respondent until the Judge calls your case. One possibility is the Safe Horizon Reception area in the courthouse – ask the court officer where that can be located. Make sure that a court officer knows you are there and where you are waiting. You can ask a court officer to escort you from one location to another or to help keep the respondent away from you . . .”

    3. Worldwalker*

      He won’t turn into a stalker — he is ALREADY a stalker. Just one who has his victim right at hand, so he doesn’t have to do any of the more dramatic stalker things. But when he doesn’t, he will.

  27. Meghan*

    Oh my god. Please get out. Please update when you’re safe (or before if you need more help). This is an incredibly damaging situation for you to be in. Best wishes, OP.

    1. EPLawyer*

      THIS. Please let us know you are safe. OR if you need help. This community is pretty good about helping people, if we can.

  28. I'm A Little Teapot*

    OP, you might find some of the resources meant for domestic violence victims to be helpful, at least in terms of helping you think through specific steps you should take. Normally they don’t apply to work situations, but this isn’t a normal work situation.

    The Gift of Fear and Why Does He Do That are two books that might be helpful. Basically, I’m pointing you towards abuse/dysfunction/manipulation/mental illness type resources because they seem applicable. If they don’t help, ok. But if it does help, great.

    1. my cat is prettier than me*

      I agree with the Gift of Fear suggestion. I worry that if OP gives notice, the CEO will retaliate.

      1. Venus*

        I disagree with some of his stuff, but the part about never, ever responding to a creeper is very useful. If someone finally gives in to the 27th phone call and answers just to yell at them, then the creeper learns that they get what they want after 27 calls.

        1. I'm A Little Teapot*

          Yeah, the book definitely isn’t perfect, but there’s a lot of good stuff in it.

    2. Keymaster of Gozer (she/her)*

      This is good advice. A lot of the help I got when I did escape an abusive relationship was concerned with removing/blocking the power he had over me and getting out from under his control. Which would be applicable here too – this guy IS controlling and it’s getting worse.

    3. SJ (they/them)*

      This is what I was coming here to say. OP, I’m so, so sorry you’re dealing with this. It’s so frightening and extremely not okay.

      I would especially recommend reading up on safety plans for those existing abusive situations. This is a known process that exists, safely leaving someone who is obsessed with you, and there are resources to help you think through your plan ahead of time, lock down your information, and so on.

      Some of the common tips include: do not give any hints that you are leaving. Get your ducks in a row, wait until he’s out of town, and disappear.

      I second the recommendation for Why Does He Do That. Really changed my outlook and has a lot of good material on the relationships between mental illness and abuse, how someone can genuinely need you and also still be abusive and also *you still get to leave*.

      It is always okay to leave.

      You mentioned your marriage. I sincerely hope that your partner is someone you can be honest with about this, that you are in a distressing situation and need help getting out.

      I will be rooting for you with all my heart.

  29. GooglyMooglies*

    I got halfway through and had to skip straight to Alison’s reply to make sure I wasn’t making up the panic I was feeling for OP. “Get out get out get out” no kidding. You MUST be aware that Alison’s range of replies go from “you’re out of line” to “this sucks and I’m sorry, leave when you can” to “evacuate immediately” and this is beyond option three. Honestly: quit, tell them you can’t talk about your next move, and block their numbers.

    1. Lexi Lynn*

      If you are concerned about losing the income, you may want to speak to your local unemployment office. This is terrifying enough that you should qualify, but keep documentation for when he fights the claim

  30. Jane Bingley*

    Oh, this is SO horrifying. I’m so sorry.

    EA here with a wonderful relationship with a great CEO. In addition to Alison’s examples, some ways my CEO and I are close include things like:

    He’ll vent to me about a frustrating meeting or difficult conversation. He’s cautious to protect my relationships and friendships at work, and never speaks badly about other employees – the focus is on his feelings and the challenges he needs to overcome, not targeting the person.

    He’ll give me a heads up when family and work life cross (eg: his wife’s schedule will be crazy for the next few months because of a new project at work; please make sure he can always drop the kids off at school and no early morning meetings til Q3).

    We’ll share polite, surface-level updates about our families and friends (I’m seeing my BFF this weekend, his kids are feeling better after a week of bad colds).

    He keeps me looped in about his personal preferences and quirks when it comes to his travel, because I book it for him (making sure there’s a pool at the hotel because exercise is a key part of his routine; always booking an exit row seat because he’s quite tall).

    Our work is still mostly remote, but when we need to meet in person, he’ll typically buy me a coffee or meal, pay for my parking, and other small kind acts that aren’t required but are greatly appreciated. He also gives generous but very bland or neutral gifts for my birthday and Christmas – typically a card with a kind note about how much he appreciates me and a gift card for a store/restaurant he knows I like.

    We are far closer to one another than anyone else in the office; we meet for many hours every week, and I know things the other members of the executive team and the board would never know. But it’s just an intimacy around WORK. Our personal lives stay largely personal, no more intimate than a typical work friend.

    I love my job, because he’s a lot of fun to work for – he has a good sense of humour, he sets high standards but gives me a ton of freedom to work in whatever way makes sense for me, and we do just get along. In an alternate universe we’d be pretty good friends, and I think that’s a good trait for an EA and CEO to have. But in this universe, he’s my boss, I’m his employee, and we’re as close as a boss and employee should get.

    1. BritSouthAfricanAmericanHybrid*

      I totally echo this! I worked as an EA for 8 years for a CEO. And you are right about perhaps being friends if you weren’t in the boss/employee situation. I left my EA position in 2017 and in the intervening years my husband and I have formed a close relationship with my former CEO boss and his wife. We just get along.

    2. BigHairNoHeart*

      Thank you for providing a really good picture of what a close but professional relationship between an EA and a CEO should be. I hope OP is able see this as a useful model if they decide to find EA work elsewhere — they DON’T want to fall into old unhealthy patterns just because it’s what they’re used to from working with this weirdo.

    3. Southern Ladybug*

      I just want to say I think this is a really helpful response to show what a positive, appropriate close relationship with a CEO/EA looks like for the OP to have as a comparison (and for the future once she’s safe).

    4. Jane Bingley*

      (Thanks for the kind remarks!)

      I would also add: while my boss was upfront in my first interview that this is not always a 9-5 job with typical hours, he is extremely respectful of my time.

      He encourages me to keep consistent hours when I can, and is incredibly accommodating of flex time use around appointments and commitments. He doesn’t track my hours and is focused on my job tasks, not time spent at my desk.

      He’s clear about times when I’ll be needed outside regular business hours and gives me lots of notice. When something unexpected pops up, he’ll try to solve it himself first, and if he needs to call me on an evening or weekend he’s always apologetic and appreciative. If something takes up a big chunk of my evening or weekend, he encourages me to take an equivalent amount of time off.

      He has never interrupted a vacation or sick day, ever, even though I’ve encouraged him to if something urgent comes up. I’ve occasionally come back from a few days off to discover drastic news he could have really used my help with, but he goes out of his way to handle anything that comes up on his own.

      I feel incredibly fortunate to work for him. I wouldn’t have guessed being an EA would be my “dream job”, but as Alison so often says, it’s hard to spot a dream job ahead of time because it depends on the people and the culture.

    5. Elizabeth West*

      What a great picture of how this work relationship should actually function. Your boss sounds awesome.

    6. Hakky Chan*

      Yes, as an experienced EA, this is the type of relationship you should be expecting between you and your executive. The core of my job is to take care of the details so that my executive can focus on the big picture, but that means making sure important conversations don’t fall off the radar, and making sure all the details for a business trip are compiled for them to easily access as needed.

      Yes, you do occasionally get to hear some frustration, but like as Jane Bingley mentioned, it should never be personal.

      OP, I mirror the message of everyone else. This is so unhealthy, and I hope you can leave the situation safely.

    7. Mallory Janis Ian*

      I was an EA and yes, all the above describes what the relationship was like. All the closeness was around work, and sometimes I was privy to things that others weren’t precisely because I wasn’t one of the affected parties. All the personal chit chat was surface level pleasantries and things I needed to know for scheduling.

  31. BritSouthAfricanAmericanHybrid*

    I echo allllll of the above. I worked as an EA for 8 years for a high-powered executive and I can tell you from personal experience NONE OF THIS IS NORMAL!! I had (and still have) a great relationship with the CEO of the company I worked for, but the lines were not blurred. He has his family, I have mine – we all know each other because of the type of work we were involved in, but he would never in a month of Sundays try and mentor me in the way you describe. And three hour calls that aren’t about work?? Where is the CEO finding time for that? Mine was on the go all day long, there just wasn’t time for long leisurely personal calls.

    RUN FORREST RUN.

  32. Keymaster of Gozer (she/her)*

    Regardless of the level of management – local team, department director, CEO or even owner of the firm – it does not give them the right to be creepy.

    Fishing for personal information, demanding you take on emotional labour, wanting you at their side constantly is not normal.

    My best friend is the executive assistant for a senior director at a large (UK) firm and I read this out to her. She went red and practically shouted ‘do NOT be alone with this guy or give him any personal data about your life and home. He’s escalating’

    Also she quit a job about 10 years back as an executive assistant when the boss basically stated that her job was to do ANYTHING he wanted. Like sleeping with him. So she’s got a good danger radar these days for creeps.

    Look for another job but in the interim do the ‘work to rule’ thing. Which doesn’t involve early morning/evening phone calls where he tries to make out your his therapist.

    1. Sara without an H*

      What Keymaster said. Now is the time for OP to set up very clear boundaries and give Creepy CEO absolutely NO personal information at all.

      I know I harp on the need to keep off-site documentation of questionable behavior, but now is also the time to start a file on a personal account and download copies of email, pay stubs, and any other documentation.

      Given the bizarre nature of the situation (I’m still shuddering), OP may also want to consider getting some legal advice. Not with the idea of filing a law suit, necessarily but to get a sense of what her options are if (when) Creepy tries to retaliate on learning that she’s leaving.

  34. HugeTractsofLand*

    Please be careful when (not if!) you leave this company. Enlist your spouse’s support and/or friends/family members, because your boss likely has deeper hooks in your mental state than you realize. If your boss threatens to blacklist you or not serve as a reference- GOOD! His judgement is so skewed, I wouldn’t trust any reference from him. Try to use someone else that you’ve worked if you need a reference. Also, I wish you the very best recovering from your time with this man. None of this is your fault- it sounds like you’ve even tried to set boundaries before- but please, please take some time for yourself to decide what you want your post-crazy boss personal life and work life to look like. Good luck and take care!

  35. President Porpoise*

    OP, this wouldn’t be appropriate for someone pursuing you romantically or socially, either. This is super not-normal, and you and your spouse both need to come up with an action plan that details exactly how and when you’ll leave. You may want to at least temporarily leave the area – take two weeks and go and explore a different state or country (you clearly need an actual vacation, and it would probably be good for your relationship with your spouse). I will say, given that you’ve been there for a while, you might want to line up any other reasonable job before you go, so that there’s no real expectation of talking to references at your current job – because you don’t want this guy getting wind of it and blocking you, and you never, ever, want him to act as a reference to you.

    Be safe.

    1. Insert Clever Name Here*

      This is an excellent point — there is literally no relationship where this type of behavior is normal or ok.

    2. Jora Malli*

      And OP, when you get a new job and new insurance and find your feet financially, get yourself into therapy. You worked closely with a manipulative abuser for an extended period of time, and that’s done some things to your brain that you’re going to want to unravel.

  36. UKDancer*

    Yikes this is deeply inappropriate and really intrusive. Run now and don’t look back.

    In my experience executive assistants work well when they work with the boss as a team, so they will deal with things that make the team happier (e.g. organising reward and recognition activities for the boss) or make work run more smoothly (meetings, making sure the boss has the information needed to take decisions and be most effective in meetings).

    The closest I’ve ever seen to being involved in their personal life is when we had an uber boss with a very serious nut allergy. As we did not want him going into anaphylactic shock the EA took her role as making sure any catering provided a separate meal very seriously. She would make sure we had ordered a special meal and that his meal was wrapped separately and uncontaminated. That’s the closest I’ve ever seen to someone being personally involved.

    In my career I’ve never known anyone be as demanding and personally intrusive as the boss described by the OP.

  37. Sabina*

    PLEASE RUN, before he is breaking into your house and boiling your bunny. I wish I was kidding…

        1. President Porpoise*

          Oh, good. That’s somewhat better than something Sabrina had seen irl.

          Clearly I need to go watch that movie. Sheltered childhood and all that.

          1. Hlao-roo*

            Fatal Attraction is a good movie and an apt reference for this letter. It’s not about a work relationship and the gender dynamic is flipped (the movie is about a woman stalking a man), but it is a very good look at how one person feeling entitled to another person’s time and attention escalates from annoying but manageable to scary and dangerous.

          3. Seeking Second Childhood, CTA*

            It may be one of the ones where you just want to read the spoilers on Wikipedia. No need to give yourself nightmares.

  38. The Original K.*

    “His statement that he waited for years before you came along and he chose you … this is frankly rather frightening, particularly in the context of the rest of it, and again very culty.”

    This was the part that sent chills up my spine. Quit, give no notice, leave no contact information and block him in the places he has access to.

    1. SMH*

      Agreed 1000%. This came across as an indication that he has been planning to control/manipulate someone for years and believes OP is the perfect person. I would be curious if OP had contact with prior EA for this CEO if their stories would be very similar.

    2. londonedit*

      Yep that was the bit where my brain just went NOPE NOPE GET OUT GET OUT GET OUT. I was quite pleased to see that Alison’s first line was exactly that response!

  40. cecildeville*

    Run, OP.

    That out of the way, how would one handle the running, in this situation? It’s often the case that you might not want your current boss to know when job you’re hunting. But here, where it sounds like OP is a good EA but new to the role, how would they go about finding a new job at another company when it sounds like their boss must not know they’re leaving and can’t be depended on to give a good reference, and their whole job is working closely with their boss?

    I mean, this situation is so dire I’ve resigning effective immediately is on the table, even if you have to take an entry level job to tide you over but. Again: Run, OP.

    But I’m curious how the commetariat would make their run in a case like this.

    1. LadyByTheLake*

      Luckily the market is good, so I think that OP should be able to find something. As for the reason for leaving, I think the OP could simply say, “my boss wants me to travel with him for work and it was more travel than I wanted.” The notion that an EA would routinely travel with the boss is just . . . no. If anything, you need the EA back at “home” holding the fort down. Just that fact will tell any interviewer everything they need to know about why OP is leaving.

    2. MsM*

      Honestly, I don’t think it would be out of line to say “I left because it no longer felt like a safe working environment, and unfortunately, former boss was a significant factor in that. If you need a reference who can speak to my work there, here’s contact information for [coworker/client/other professional contact who can be trusted not to give boss updates].” If wherever you’re interviewing isn’t going to take that seriously, do you even want to be working there?

      1. AnotherLibrarian*

        While I agree that OP needs to GET OUT, I would be really careful about the phrasing, because, honestly, as an interviewer you never know if the person interviewing is really in a bad situation or is just a weird person who finds someone telling them they need to show up on time a personal attack (yeah, I worked with a guy like this once, he was a much of a delight as you can imagine.) So, I would instead get a colleague to act as a reference and use bland language about why I was leaving. If the job wanted to talk to my manager, I might use something like, “My manager isn’t aware I’m job hunting; however, I have several other colleagues who can speak to my work.”

    3. misspiggy*

      One option would be agency work. Temp cover for EA absences can be well paid and can help cover one’s tracks.

    4. Critical Rolls*

      I would quit remotely and with no notice if it were me, because I can’t imagine the stress of trying to secretly job hunt under these circumstances, and I agree with other comments that there’s no way of predicting how this lunatic is going to react.

      Regarding the search, she might not even be asked, and can put a standard “seeking new opportunities” type explanation. But, if needed: “The expectations at my last job shifted dramatically in ways I was very uncomfortable with. But I did get very proficient with X, which looks like it’s a central component of New Job.” I’d go with something like that, and hopefully the interviewer will be able to read the “yikes on bikes” between the line and not dig further (in fact, it’ll tell you something if they won’t drop it).

    5. Working Hypothesis*

      I would:

      – Document everything that he ever did that felt off in any way (because I didn’t feel sure I could tell which ones were and which ones weren’t by now). Save evidence where possible, on private devices that have nothing to do with the company.

      – Quietly change the official address that’s on file in the office records, without telling my boss I’m doing it, to a post office box. The kind where the address doesn’t LOOK like a post office box, it looks like a street address, so he can’t tell.

      – Quietly bring home all personal items that I have at the office. Wipe all personal documents or other data from office devices.

      – Tell my husband that I’m about to be leaving and why. Warn him that the sh*t is REALLY likely to hit the fan hard, and we probably want to be someplace else for a few weeks at least.

      – Leave the house for this few weeks. Go on vacation with my husband if possible; if his employment doesn’t permit, then stay locally with family or friends for a bit. Leave security cameras on at my house, so I’ll have data about anyone who might come around while we’re gone.

      – Send in a letter of resignation, by email, not giving any indication in that email that would let them know you’re currently anyplace except at your own house. If there’s anybody to send it to besides the boss (a new HR person, for example) then do that. Don’t communicate directly with the boss if at all avoidable. Don’t give any reason why you’re leaving; just make clear that this decision is final and you do not wish to hear from anyone at the office again except to be sent your final paycheck, which should go to (insert the post office box that you already set as your official address in your office file).

      -IMMEDIATELY block boss on everything. Social media, phone, LinkedIn, whatever. The one exception: leave him free to email you, but set up an automatic folder into which those emails go, without your having to see them at all. Delegate a trusted friend or family member to look at that folder every once in a while to see if there’s anything there which they feel you need to know about for your own safety.

      – Start looking for a new job. The answer to why they left the last one should be, “The job description changed and I was being asked to do things which I wasn’t comfortable with.” Try to line up references that aren’t at that employer… because even if your references are other employees from there besides your boss, if they know how to reach you or your (former, by this stage) boss thinks that they might, they will be under enormous pressure to yield up your contact info. Also, you saw what was said about the HR rep… assume that’s the kind of thing the other staff will be told about you after you depart.

      – After two or three weeks, if the emails in your “Creepy Boss Folder” don’t turn up anything truly scary, send someone (maybe your husband, maybe a friend) to your house to examine the property and the footage from the security cameras. If everything looks safe, you can probably go home, though you’ll want to keep good home security for quite a while.

      – If there are scary things either on the security footage or in the emails, contact the police. If there are nasty things in the email, or threats to your career but not stalkery/violent stuff, contact an employment lawyer.

      -Regardless of what happens afterwards, find a therapist if you don’t already see one, and start to work on untangling the mess this guy has made of your head. That’s all unfortunately likely side effect of this kind of abuse, and it may take a while to sort it out. Professional help if a good idea.

      -UPDATE ASK A MANAGER BECAUSE EVERYBODY THERE IS SO WORRIED ABOUT YOU AND WILL WANT TO KNOW THAT YOU’RE OKAY!

  41. LolaBugg*

    Your resignation can simply be the gif from mean girls of Regina George saying “why are you so obsessed with me?”

    I kid, but that’s what was going through my head when I read this. I would be so deeply uncomfortable and creeped out. You are not alone feeling that way. I hope you can get out soon.

  42. teensyslews*

    If I were you I’d document all of this, package it up nicely, then write up a resignation letter with no notice period (that specifically states not to contact you after your last day) and and submit it to HR directly with the package. BCC your personal email. This guy is absolutely gonna lose it when you resign and the most distance you can put between you two in that resignation and the more you can make sure HR has proof of his obsessive behaviour (and state explicitly that this is why you are leaving and that you are not comfortable) will hopefully make the transition more smooth. Failing that, you will at least have a good paper trail to fall back on with the company if you need to take legal action. Best of luck to you!

    1. AllTheBirds*

      All excellent advice, and perhaps contact an employment lawyer and give her a copy of the HR packet as well, ASAP.

    2. InfoGeek*

      Do not BCC your person e-mail from your work e-mail.

      Assume that the company has access to your work e-mail.

      I know that the recipients can’t see who is BCC’ed, but the company should have access to her e-mail as SENDER, so they can see where it goes.

      Also, don’t transfer things to home by sending it to your person e-mail from your work e-mail.
      Assume that CEO can access everything — things on the computer you’ve been using, your work e-mail, texts on a work phone, Teams messages, etc.

      2. Worldwalker*

        Get a burner Gmail account, send it all there, forward from there to a personal email.

      3. SoloKid*

        Saving the original sent message to a flash drive can also work. This shows sent date, sender, recipient etc.

        Gmail -> Sent folder -> “More” (three vertical dots) -> Show Original. It’s basically a text file.

  43. Eggo*

    RUN. I was an EA for my boss for 4 years and I did things like take his dog to the vet/groomer and other personal/family tasks that were *outlined* when I was hired. We rarely communicated outside of M-F, 8-5pm. He never pushed me to do things that I was uncomfortable with (There was a talk about me going to his townhouse in AZ to accept delivery on some new household appliances but I shut that down quickly). Your boss is SO FAR out of line!

  44. londonedit*

    This is. Creepy. As all. Hell.

    If you can at all afford to do so financially, I’d quit now. Do not pass Go etc. If not, you need to be seriously job-hunting with the aim of getting out as soon as is humanly possible. This has literally given me cold shivers down my spine – it’s so far away from normal that I don’t even know what else to say apart from RUN.

    1. Keymaster of Gozer (she/her)*

      I had to take one of my calming meds after reading this because it is so, so close to the dawning horror that was my ex. Getting away from him involved not only changing my number (and being very selective who gets it) but also reformatting my computer and anything else he’d had opportunity to put tracking stuff on.

      Granted, I am extremely paranoid IRL anyway but I’d recommend OP at least get a new phone number for personal use and not give it to her boss.

  45. Anonforhere*

    Not to scare the LW out of running, because you definitely need to RUN, but I feel like the replies are kind of glossing over just *how* alarming this really is? If this guy were a spouse instead of a boss he’d turn violent when his victim tried to leave, and I’d guess there’s a decent chance he still might. Please alert anyone you can trust to be sensible about it that your boss may be stalking you. And maybe an organization that helps domestic abuse victims could also help in this circumstance?

    1. Meep*

      A million times this.

      My former boss is a woman and had a lot of these red flags and the same strange mannerisms with me (also a woman). If she wasn’t a VP and I wasn’t an engineer, I could say I wrote this. It was definitely abusive. I suffer from C-PSTD as a result and I was terrified of her showing up to work and shooting me when I reported her, because she had threatened it before – on top of going out of her way to find my address when I moved. So much this.

    2. quill*

      YES. The main thing that will make this easier for LW than escaping a partner is that he does not have access to her home / possessions. But that doesn’t mean that he won’t try to escalate when she leaves, just that leaving doesn’t have to include finding a new place to live right away.

      Actually, OP, if you could resign while he’s out of town on that trip… it might be easier, practically, to do so and therefore get a head start. (Don’t postpone leaving for that trip! But if it’s coming up and you need a date where all your ducks for resignation with evidence of his creepiness and absolutely no way that he can bring legal consequences on you without making a judge laugh, definitely hurry so that it’s all ready when he’s not in the office.)

  46. Dom S*

    It’s a pity comments are text only, as I was definitely going to pop up the movie poster for Get Out….

      1. ShysterB*

        Frankly, I’m surprised someone hasn’t already posted it as a comment to the AskAManager Twitter post.

        I hope OP gets out quickly, and safely, and lives their best life after this.

      2. Ali + Nino*

        My inner monologue alternated between “Girl, you in danger” and “NOOOOOOOOOO!!!”

  48. Bernice Clifton*

    Leave as soon as you are financially able to do so. This boss will take your resignation as a Betrayal no matter what or when, so best to do it now.

    As for what a good vs bad EA/Exec Relationship looks like, Alison’s examples are good. It can be a social relationship, like showing him a picture of a couch you’re buying if that’s his thing or him asking about your weekend or how a trip went. It is NOT monopolizing your time or telling you to reveal personal info about your background.

  49. Radical Edward*

    YIKES ON TRIKES

    If at all possible, don’t even wait for another opportunity. Give notice *immediately*. The story about relocating is a good one – it’s ostensibly something you can’t control and makes ‘changing contact information’ more plausible.

    You need to ghost this person and you need to accept that that might mean ghosting anyone who’s sympathetic towards them too.

    I saw a version of this go south very quickly once the victim made the effort to disengage entirely. They were safe, but the aggressor ended up causing a massive public scene. You need to mentally prepare yourself for the possibility that this person will become angry and/or full-on stalker-y. Inform multiple people you can trust and make sure they understand that you’re getting out. Give them as much detail as possible; you might need corroboration later on.

    Good luck, be safe, we’re rooting for you.

  50. Dona Florinda*

    OP, this is predatory behavior. He is trying to isolate you in everything possible way, and so far he’s being successful.
    Get out, now.

  51. Not Tom, Just Petty*

    I saw this job on a Bored Panda post.
    Assistant to CEO. Make sure he stays focus on his tasks, make sure he takes time for himself. Make sure he eats and exercises. Prepare food, clean up, do laundry. Make sure he is prepared for and attends all meetings. Make sure he has time to be the innovator we need him to be.

    People laughed, like how could this ever manifest into a real position?
    Using the same techniques as all cult leaders, I see.

    OP, I cannot stress this enough. GTFO. Once you are far enough away (professionally, like a year into your next job) block him and the company from everything.

    1. CoveredinBees*

      Many people believe that they can turn an executive assistant into a personal one as well. There may be some personal aspects involved (“My sister is very ill please book me a flight to Des Moines ASAP.” or “Please make sure June 10th is blocked off from 5 pm because it is my anniversary.”) Some people will keep pushing this boundary until they are stopped.

      1. Not Tom, Just Petty*

        My first thought reading your reply was “Indeed.”
        That made me think of the job search site.
        I know there’s a pun in here somewhere!

      2. quill*

        This is more than I did as a babysitter, granted I only ever sat for kids who could tell me when they were hungry, and use the bathroom by themselves.

        This CEO doesn’t require a babysitter, they require the court of Louis XVI. To constantly shower them in attention even while they poop.

      3. SoloKid*

        lol now there’s a job for all those people that put “working parent” on their resume.

    3. Ruby*

      I immediately thought of that posting too.

      Is this some new weird tech bro stuff? They all think Pepper Potts is real life?

      1. Anon and on an on*

        Agreed. And I after this letter, I believe that if that position gets filled, the reality there will be worse than the posting.

  52. Meep*

    As someone who was there for five years, don’t try and work through it. It won’t work. Just find a new job and move on.

  53. The Rafters*

    The entire thing from start to finish is as creepy AF. My hair is standing on end. I’m going to address the HR person even though they’re gone, because everyone else has already given you their *get out* advice with regard to the CEO. Most of the HR folks I know go out of their way to be friendly, but not “friends,” or “work buddies.” This is to protect everyone from even the appearance of misconduct, cover-ups, etc., so that was bonkers on its own. In the future, you should keep friendships with HR in check as well.

    1. Not Tom, Just Petty*

      This just formed random nagging thoughts into a coherent question:
      CEO began grooming two staff members. As their twisted initiation continued, they became friends.
      Now one is gone.
      The one who was a pathological liar. The one who was committing fraud.
      I believe OP believes this. I believe OP was told this.
      I also believe that OP made it to the inner circle.
      HR person did not make the cut and is now being blackballed.
      Why believe anything this guy is saying?

  54. Karen Wiseman*

    Get out.
    Do EVERYTHING you can think of to stay safe even if it feels like you are being silly. FAR better to look back in a few years – remember when we changed all our phone #s and went out of town for a few weeks? than to wish you had. I was an EA – NONE of this is normal.

  55. Carcarjabar*

    Oh goodness…. this is the start of a horrible Netflix movie that I can’t seem to turn off… OP- please don’t be the star of this movie. There is *absolutely* nothing good that can come out of this situation. Once you get out and have a chance to decompress, seriously consider talking to a professional about what you experienced, and how it affected your marriage. Marriage counseling might even be warranted. Don’t let this experience damage your marriage or your future jobs.

  56. IT But I Can't Fix Your Printer*

    YIKES. In case you need another reason to leave, this is not doing anything for your resume. Putting “listening to everything the CEO says for hours and hours” and “attending business trips where I had no tasks to do” are not demonstrating any accomplishments that will get you a reasonable administrative job in the future. I hope you can move on quickly!

  58. Liz T*

    This is genuinely scary. Like, consider moving and not telling him your new address, and then sending in your resignation like that intern who got a dick drawn on her cast.

    I’m genuinely alarmed for you and want you to be able to leave quietly today and never return.

    1. UKDancer*

      This so much. I’ve never known an EA travel with the boss. I mean they usually make the travel arrangements but never actually go. That strikes me as deeply creepy and inappropriate and reminds me of the opening of an episode of Criminal Minds or CSI. So many red flags.

      2. MsM*

        I’ve had a few situations where the EA tagged along on CEO trips. But we’re talking small nonprofits where the EA also functioned as a member of the fundraising team, and was there to help prep for donor visits and coordinate last minute event arrangements. And of course, the EA wasn’t expected to be glued to the CEO’s side outside of meetings, let alone be there just to be there.

    2. BA*

      This.

      There are certainly times when people have to travel at times that conflict with other things, but those are to events where the person’s presence is NEEDED and IMPERATIVE. Not to be a travel buddy for their infantile boss. A good boss would even try to make arrangements so you don’t need to travel if there’s a personal milestone event you want to attend.

    3. Em*

      I’m thinking of this awful story where a college age woman’s boss at a home and garden center was obsessed with her and killed her while they were at a wedding that he coerced her into attending with him… shudder.

    4. Keymaster of Gozer (she/her)*

      Absolutely. He is not safe.

      And if he comes up with some ‘but I have to have you there otherwise I forget details/need a confidence booster/I absolutely have to have someone with me when travelling because (insert whatever medical or other conditions here)’ reasoning as to why you have to go just offer a printed itinerary/checklist instead.

  61. Bagpuss*

    I agree with everyone else that this is definitely so far from normal that you should be urgently looking for a new job and leaving as soon as you can, and maybe have conversation with your spouse and agree a timescale for you to leave even if that means leaving before you have a new job, if that’s possible with your family finances etc.
    You don’t say how big the company is, so I don’t know whether it’s large enough that you would still be able to get HR to provide a reference, or whether there is anyone else who might be able to provide a reference.

    As others have said, this goes well beyond the normal role of an EA – I have a friend who sued to work as an EA / Personal Assistant to a very successful creative person – my friends role was very varied due to the nature of boss’s job – definitely not just 9-5, but didn’t demand anything like the thing you are describing. For instance, when her boss suffered a personal bereavement her role was about booking travel, cancelling and postponing bosses planned appearances etc, not providing ’emotional caretaking’. It did sometimes involve calls before or after normal working hours but they were always work related and almost always due to boss being in a different time zone. And her pay reflected those job requirements.

    2. londonedit*

      Yeah I’ve had a couple of friends who were EAs and the sort of things they told me about that I thought were crazy were things like having to stay in the office with the boss and the rest of the team until 1am working on something super important (if I remember rightly the boss ordered pizza in the evening and the company paid for them all to take taxis home) and a time where my friend got a call from the boss at 5am because he was on a work trip and there was a problem with his flight. OP’s description makes those examples sound like the most boring 9-5 office job in the world. None of this is in any way normal or acceptable.

  63. BA*

    This is straight up creepy behavior from your boss, and I’m sorry you’re having to go through it. You don’t need to be granted permission to leave, so don’t phrase your resignation as anything other than a closed statement. Don’t offer 2 weeks. Career-wise, you don’t need to worry about how this looks for your reputation. You’re exiting a toxic and abusive relationship. You don’t need to fight through a terrible two weeks just to secure a good reference. When you move on to your next role, you’re going to not want the new employer to contact him anyway, and can explain that it was an abusive relationship and you don’t want your old boss to know where you are working. Any new company worth a darn will understand.

    I don’t know about the legalities of this, so someone may be able to help fill in the blanks, but you may want/need to consider some sort of no-contact order that gets presented to the boss, as well. Their actions lead me to believe that you won’t stop hearing from them after you quit.

    1. Tib*

      Yes, don’t worry about burning this bridge; it’s already exploded with mushroom clouds. Just get yourself out, now. Can you temp if you need an immediate income?

  64. HumbleOnion*

    The OP doesn’t specify a gender (unless I missed it?) but how many of us imagined a woman writing this? It’s scary and abusive. I really hope the OP makes it out soon.

    1. learnedthehardway*

      I thought it was a man, and the EA was a woman, and the only thing that surprised me is that the letter didn’t detail that the CEO was trying to get the EA to move in with them / have a sexual relationship with them.

      In other words, OP – get out and put this FAR behind you as fast as possible. The whole thing is extremely unhealthy.

      2. Scrotes be mad*

        I’m sure the part where he demands a sexual relationship or move in with him is coming but just hasn’t happened yet. Not exactly original material here but your right, more red flags here than a Chinese parade.

      3. quill*

        The travel sounds like his chance at escalating something. Alone in a new place and dependent on him for the return trip? Extra double triple NOPE.

    2. Scrotes be mad*

      I don’t think it even needs to be said. We all have seen this play out a million times with men in power over women. You never see the opposite.

      1. Isben Takes Tea*

        I would like to gently push back on your last sentence: I agree that it is a fairly safe assumption to think the CEO is a man and the EA is not, but this situation does in fact also happen in other gender combinations, where there is often an added layer of others not taking the situation seriously because it’s not the expected dynamic.

        This behavior is supremely alarming regardless of genders.

        1. Scrotes be mad*

          This is two different things. You can’t just swap the genders in this scenario and pretend it’s the same thing. One of the scenarios is a well documented frequently occurring phenomenon, the other is not. One puts the emotional and physical well-being of the woman at risk and the other does not. One has been historically supported by the patriarchy and the other is not. Are there stripeless zebras and black swans, technically yes. With that being said I concede that “never” is a very slight overreach. The way that men use women for emotional labor versus the way that women use men occur on two vastly different levels with vastly differing levels of harm.

          1. Isben Takes Tea*

            I 100% agree with you that it’s not the same thing, and didn’t mean to imply that different gender combinations don’t have different dynamics. I agree wholeheartedly that it is usually men taking advantage of women, and that women are usually the most at risk (especially physically), and that it is a very serious problem.

          2. Alpacas Are Not Dairy Animals*

            Women doing this to other women is also well-documented and can cause tremendous damage, it’s just usually dismissed as “bullying” or “drama” because abuse by women towards women is seen as childish and harmless.

            1. Scrotes be mad*

              We weren’t discussing woman on woman abuse or bullying. We were discussing how male entitlement is so ubiquitous and innately conditioned towards expecting women’s emotional labor to the extent that it’s very unlikely that OP is a male. This reads like when people bring up black on black crime when discussing Black Lives Matter.

              1. Isben Takes Tea*

                Maybe we were coming at the original comment from different places. The discussion was around gender implications of this dynamic: you are very right in that male entitlement is ubiquitous and innately conditioned towards expecting women’s emotional labor, that this is a major societal problem with heavy repercussions, and it’s very likely the OP is not male.

                But because the OP did not specify their gender, I was coming at it from the perspective that even if our (likely) assumption is wrong and you stripped away the additional layers of gender dynamics, the base behavior is extremely problematic and abusive. Alpacas Are Not Dairy Animals was adding to that point.

                Neither of us are wrong, but we might be having two different conversations.

              2. Scrotes be mad*

                You may be right, I think we might be approaching the conversation from different angles too. We are still left with terrible boundaries and a power dynamo even after stripping away the gendered layers from this issue. I am a little surprised that Allison left the gender of OP open to speculation. I suspect from what I am reading that I’m not the only one.

                Maybe I’m spoiled from my time on Reddit where it’s pretty standard to include gender. A poster with a question often format it like this for example: “I (28F) am having trouble getting along with my partner’s (32M) child (11M) from a previous relationship, what do I do?”
                It’s a little bit of an eye sore but it’s economical in terms of space and it conveys gender. I wonder if something like that could get normalized here as opposed to dozens of posts speculating on gender of posters.

                1. Ask a Manager* Post author

                  I don’t always know the gender of letter writers.

                  I’d rather people not derail on it unless it would change the advice, which in this case it doesn’t.

        2. zillah*

          yeah, i think that this is good to keep in mind – not because the behavior isn’t heavily tied to gender and needs to be addressed on a societal level (it is, and it does – this kind of behavior is absolutely deeply gendered and rooted in misogyny), but because this kind of behavior sometimes happens without those added gender dynamics and is still deeply alarming without them.

    3. anonforthis*

      Yep, but to be clear this would still be wrong if the ceo were a women and the OP were a man. Or if they were the same gender. It’s just that there is a pattern of men usually doing this to women…

    4. Quaint Irene*

      The title of the post is “The CEO is obsessed with me and wants me to be HIS emotional support.” (emphasis mine

      1. Worldwalker*

        Yes. It’s stated that the CEO is a man. Also that the HR generalist who the OP became friends with was a woman. It’s probable that the CEO’s fixation on the OP is to some extent sexual (even if not overtly), and as such, the odds are about 9:1 that the CEO is straight, so if the OP is in his target demographic, that would make her female. Plus friendships between same-sex co-workers are somewhat more common than opposite-sex ones, making the friendship with the HR person also suggest female.

        But, really, it doesn’t matter if the OP is male, female, or neither — the OP only needs to be one thing, and that one thing is ELSEWHERE.

  65. Julbroni*

    Occasionally I’ll read a letter on this site and think, “I really hope we get an update on this.” This is one of those letters.

    2. BlackLodge*

      Agreed; I would very much like to know how this turns out. We want to know the OP is safe and ok!

    3. All Het Up About It*

      I hope we get a GOOD update on this one. I’m terrifed it could be a “things are worse” type of update. I hope the LW takes the many suggestions about removing themselves safely from an abusive relationship seriously and that they have great support at home.

      Part of me is trying to understand where the spouse is in this situation. My partner would be having serious talks with me in this situation.

  66. Anon100*

    LW – these things you’ve listed are absolutely not normal for an EA. Managing schedules and emails, going with the CEO on a important conferences, giving the CEO insight on current office politics, sure. But what you’ve listed here is not anything professional on the CEO’s part. It’s straight up predatory grooming behavior.
    I’m also sure the CEO is not paying you enough in the first place, and if you have to, take a lower paying job for your sanity.

  67. Cthulhu's Librarian*

    The building is filled with murder hornets, there are pigeons crapping everywhere, and someone has also set it on fire. It is time to flee, OP. Flee for your sanity, flee for your life, and flee for the well being of your relationships with everyone you care about. You’re rapidly approaching areas where faking your own death to get out of things is acceptable.

    1. quill*

      Yeah, also that HR generalist? If you got your information from the CEO, there’s a chance none of it is true. And if that’s the case expect the CEO to try and pin something on you on your way out, or attempt to interfere with your future jobs.

      1. S*

        Yeah. I would hate for OP to discover that she’s the apparent author of this year’s tax fraud or something.

  68. Sparkles McFadden*

    Document EVERYTHING. Make copies of emails etc. Quit and DO NOT give notice as you are just inviting two weeks of emotional abuse and manipulation. This is a bridge you want to burn.

    Get counseling. Find resources that help victims of domestic abuse or stalking.

    Contact an employment attorney as you may need one. I, personally, feel better when I know I am getting informed and taking action and getting prepared for all possibilities. As someone upthread mentioned, the info about your HR friend came from the CEO, so it’s likely all lies. It’s possible the HR person became a target in an attempt to isolate you, or just to punish the HR person for some imagined disloyalty.

    Stay safe and good luck.

  69. this feels too familiar*

    OP, I’ve dealt with someone similar (in personal life, not professional). This guy is deeply fked up. You cannot make this situation any better. Please, please get out.

    Talk to your spouse about quitting without notice, with no job lined up. When asked by future interviewers about why you have no reference and a job gap, your line is, “My boss took it badly when I left suddenly due to a health emergency which is since resolved.”

    I’d also recommend a few sessions with a therapist. You may need to recalibrate your sense of what normal/healthy interpersonal relations look like. A therapist can also help you learn to recognize warning signs that someone is targeting you (to clarify: it is not your fault this guy targeted you).

    Please, take it from this internet stranger who’s seen too much: this can turn into PTSD if you’re not careful.

    1. AnotherLibrarian*

      I really like this line for interviews. It sounds reasonable. It’s not unheard of and wouldn’t raise eyebrows. Also, seconding the advice for a therapist.

  70. CoveredinBees*

    Run away as soon as you possibly can afford to do so. If you have a rainy day fund set aside, it is raining cats and dogs now. I cannot overstate how abnormal this is. I used to share office space with our CEO’s EA. The CEO had issues separating personal life from professional (mostly in their own life) and the EA was both inexperienced and a frequent oversharer. As a result, I felt like their relationship often hopped back and forth over the line between professional and overly personal. LW, what you described is so many miles beyond their most questionable moments. Not even close.

  71. rosyglasses*

    This reminds me of a job ad that (at) notshrmapproved posted on their IG a few weeks back about a CEO looking for an EA… and it was essentially be his wife and mother plus an accountant, CFO, run presentations, and the like. This all raises huge red flags and I think you need to run ASAP.

  72. Not a Spawn of Satan*

    Please get out ASAP. I’ve reviewed a lot of resumes admin assistants. I’ve never seen any include “emotional support for the CEO.” Please, stay safe and get out!

  73. anonymous73*

    I normally don’t recommend quitting a job without another one lined up but if you can swing it financially, I would send a resignation letter via email, and then immediately block all ways of him contacting you (personal email/phone/LinkedIn/etc.). Dude is CREEPY.

  74. idwtpaun*

    OP, all of this sounds frankly disturbing and I’m very worried about your ability to leave. It seems almost certain that your boss will do everything in his power to prevent your leaving when you hand in your notice, making up laws and regulations that require you to give long notice and otherwise interfering. Please, don’t go along with it. You have no legal obligation to do this job once you decide to quit it. Do not allow him to draw you into conversations that require you to justify your leaving.

  75. MEH Squared*

    OP, I echo everyone and say run as fast and as far as you can–as quickly as you can. My skin started crawling around your third bullet point and completely left my body by the end of your list.

    This is classic abusive/stalking/culty/grooming techniques and I am so concerned for you, OP. Please do what you need to do to stay safe.

    1. MEH Squared*

      Just to elaborate, your CEO is so far out of bounds that it can be hard to see it because we’re not used to people flagrantly breaking societal norms. It’s natural to doubt yourself and if it’s really that bad, but I hope by the uniformity of the responses you’re getting, you can see that it really is that bad. It’s not you–it’s him, and you can leave without any qualms (I mean, you can in any circumstance, of course, but especially this one.)

      1. MEH Squared*

        Sorry, but one more thought. Please seek some professional help (therapy) if you’re able. This situation has taken a toll on you and a good therapist can help you see that it’s not your fault and how to go forward. I think everyone can benefit from therapy, especially in a situation such as this (how to untangle all the many threads, see how to spot the signs of dysfunction in the future, how to put safety measures into place, etc.).

  76. cardigarden*

    I wasn’t even halfway through and my brain was SCREAMING “run”. Quit, quit via email with HR/payroll cc’d so that you know you’ll get your last paycheck, and block his number, block him on all possible social media. Just get out and stay safe.

  78. Dinwar*

    OP, this is abuse, pure and simple. It’s emotional abuse right now, and seems likely to become physical abuse. It’s extremely likely (as others have pointed out) that this CEO has already destroyed one person’s life to isolate you. This will continue. You need to protect yourself and your spouse (and kids if you have them) from this creep.

    Leave without giving two weeks. Turn in a resignation letter on top of all work-related equipment (thoroughly wiped) and don’t look back. Ideally have someone else deliver the items–FedEx them or send a courier or something. Cut all contact as thoroughly as possible.

    Leave immediately even if you can’t afford it. Yes, it’s that important. If you give two weeks this CEO will do everything in their power to destroy you–mentally, emotionally, and professionally. This person will see you leaving as a deep betrayal, and will seek revenge. They are unhinged, and do not deserve the courtesy extended to normal business relationships. When the CEO pushes back–and they will–remember that THEY are the one who did the damage. THEY are at fault.

    Document everything before wiping your computer. Past, present, everything up to the point where you leave. If you have friends in the police force talk to them and show them the documentation. They can’t do anything yet most likely, but it will put them in a position to mobilize resources should they become necessary.

    When you leave, understand that what you’ve experienced is wildly abnormal and traumatizing, and that you have likely internalized some very bad things from this office. That DOES NOT make you a bad person (and unfortunately some folks–including the CEO–will try to make you think you are, using these as examples). These bad habits are the result of trauma, and unlearning them is part of the healing process. This will take a while.

    1. MEH Squared*

      This is a good list of practical things to do, OP. I would add see a therapist to the list (which is my recommendation in general to anyone who needs an outside perspective of a difficult situation, but especially in cases of trauma). A good therapist can help you see that this was not your fault and how to deal with the ramifications.

    4. ThursdaysGeek*

      And, in spite of ALL these comments, it may seem like perhaps people are taking it too far, it’s not THAT bad. But it is, and it’s completely normal that it’s hard to see it. It will be normal that you will feel a sense of loss, a sense that you failed in some way. But you are not to blame, you are not a failure, and you can recover from this. First, you need to get out. Please. And then let us know. We are all strangers, but we still care about you.

    5. Elsa*

      Allison, I have a question. Everyone (including me) agrees the LW should run, should resign without notice, should GTFO.

      Some people say that she should do this if she can afford it. Others say she should do it whether she can afford it or not. There is some agreement (and I also agree) that she should not resign in person, should not give two weeks’ notice, should not ask for or expect a reference.

      So my question is: What’s the next step on this? It sounds like she can’t request unemployment, even though she will have quit for her own safety, because that would mean the Creep would be involved in some way/ get more info about her.

      And applying for another job: My guess is she’ll have no trouble getting one in this market. But what should she say when her next employer asks for a reference or asks why she isn’t being given one? Should she leave the job off her resume?

      Again, since this is the internet, I just want to say I totally agree that she needs to run soon, far, and fast, but I’m thinking of the things that might keep her from doing so.

      1. Dinwar*

        Not sure about unemployment laws. If the cops get involved things change as well–it’s one thing to quit, it’s another to initiate a criminal investigation, and that could matter with regards to unemployment.

        With regards to references, the LW isn’t required to commit suicide to get a job. I don’t use that term lightly–including this CEO in ANY PART of the hiring process is going to end badly. If the LW is very, very lucky it will merely torpedo any chance of getting a job in the industry; if they’re unlucky the CEO will act as unhinged stalkers do when they think they are rejected. Minimizing contact with the CEO is a top priority, at least for a while and assuming the police don’t get involved (at which point all contact should be through lawyers/legal channels).

        I think a brief statement that the last place you worked was extremely toxic would be sufficient. There’s likely to be a rubber-necker/ghoul factor–we humans are fascinated by disasters–but I think any reasonable company would understand not wanting to give a reference under those conditions. The LW may not be believed, of course, but that’s sort of a red flag against the company conducting the interview by itself.

        Remember, this CEO is unhinged. They are NOT going to give a good reference. They likely destroyed one person’s life already, and they will attempt it with the LW if given a chance (thus the absolute need to cut all ties as thoroughly and quickly as possible). Putting this CEO as a reference both puts the LW and their family in serious danger (physical, financial, etc), it also is absolutely certain that the CEO will do everything they can to kill any chance of the LW getting the job. Not having a reference is better than having this one.

        If the LW has enough work history they may not need this reference. Or can use someone else in the company as a reference (if there’s anyone they trust).

        I wouldn’t necessarily leave the job off the resume, but including it is a risk, so it’s up to the LW how much a risk they’re willing to run. Depending on the size of the company and the nature of the industry the company conducting the interview may contact the CEO, which would give them information on where the LW is.

        1. Elsa*

          Hi, Dinwar, as stated above, I do know that the CEO is unhinged. I tried to be as clear as possible that I think this person needs to GTFO. I am aware that the CEO is not going to give a reference and shouldn’t be asked for it. To be honest, I’m not sure how I could have been clearer about these things.

          Ah, the internet. Gotta love the internet.

          1. Dinwar*

            I understood that you understood the CEO isn’t rational. I was clarifying my position for the LW, on the off chance they read it.

            It’s really easy for an abuser to distort their victim’s perceptions, and it’s even easier for the victim to distort their own–not an insult against the victim, it’s part of the trauma and it’s how the abuser distorts their victim’s perceptions. So I’ve been trying to be very clear in the “Why” behind anything I say in order to provide the rational that the LW may need in their dark moments. I’ve found it helps, when you’re at your lowest, to have something external to refer back to, to know that the doubts are part of the trauma and aren’t real. So I’m trying to provide such external references.

            I’ll be honest, this is also dredging up some fairly rough memories–my advice comes from some hard experiences, both mine and that of some people close to me–and when my emotions get the better of me my diction tends to get a bit weird. I use reason/critical thinking as a coping mechanism–think through the issue first, deal with pesky emotions later. A useful trait at work, but not so useful in inter-personal relationships, I will admit.

      2. Hlao-roo*

        The questions you ask are good ones. Concerns about finances and future job searches can definitely keep people in bad situations longer than they should be, and having a plan in place can make it easier to escape a toxic job.

        I think the first step is for the LW to sit down with her spouse and look at their financial situation. Can they afford for her to quit immediately? If not, is there anything they can pare back in their budget? If yes, how long can they afford for her to be out of a job? If they can only afford a month or two, maybe the LW looks at temp/retail/food service jobs to bring in some money while she looks for a job in her field. Because this is a safety issue, LW and spouse should think about calling on friends and family and other parts of the social safety net that aren’t unemployment (applying for UI opens up a line of communication between the LW and the company/CEO; picking up food at the local food pantry does not).

        For applying to another job in the future: does the LW have three references from other jobs they can use? If so, hiring managers are less likely to care about not having a reference from a company the LW worked at for 2-3 years. If not, is there anyone who used to work at this current company (but does not any more!) and that the LW trusts?

        If the LW judges it safer to leave this job off her resume entirely, I don’t foresee any problems with job hunting. A job gap from 2019 – 2022 can be waved away as “I left my job in 2019 for [reasons] then was not able to find another one until 2022 because of the pandemic.”

        1. Working Hypothesis*

          Several of us below have commented that we’d be very willing to help if LW thinks there’s anything we can do to make escape from this nightmare situation easier and safer. I don’t know how it was done but I do know that a kind of financial assistance effort was raised through the commentariat here several years ago, for another LW who needed it. I have no idea whether this LW needs it in order to quit with no immediate job or not, but if they do, we might be able to do something similar in order to build them a bit of financial cushion. In the current job market, it probably wouldn’t take long for them to find something else.

          1. IT geeks against creeps*

            I also hope there’s something we can all do to help LW: financially, practically with some of the tasks, anything.

      3. Critical Rolls*

        I made some suggestions above (basically, to say that expectations around the job changed in ways she wasn’t comfortable with), but I think most people understand that there are a *lot* of reasons you might not be able to get a reference from your most recent boss. LW can mitigate that if she has a peer or other person at the company who can provide an alternate reference. But if she’s really pressed, it seems like it wouldn’t be unreasonable to say, “My supervisor was very unhappy about my decision to leave and is not a useable reference.” Do interviewers really dig into this very often? I haven’t had much of an issue with it.

      4. Observer*

        It sounds like she can’t request unemployment, even though she will have quit for her own safety, because that would mean the Creep would be involved in some way/ get more info about her.

        Not necessarily. It could be that if the OP has good enough documentation, they won’t even reach out to CreepyBoss. But even if they do, that doesn’t give CreepyBoss anything but the fact that the OP applied for UEI. CreepyBoss doesn’t get to demand any further information from the Unemployment office of set conditions on responding. If he does try that, they are not going to comply and they will probably use that as useful information to evaluate the OP’s case.

        But what should she say when her next employer asks for a reference or asks why she isn’t being given one?

        There are a number of suggestions all over the discussion. And many more in other posts. It’s a surprisingly common problem, and it’s not that hard to deal with.

    6. Generic Name*

      Yes, leave NOW. Tell friends and family your are worried about your safety. Put together a safety plan on how to leave. Use the resources for domestic violence.

  79. Emotional support capybara*

    G
    T
    F
    O

    This is “put the lotion in the basket” tier creepy. Get out, block block block, change your phone number, change your locks, maybe even think about moving if you can. This is so screwed you can see the threads from orbit. RUN.

  80. Yvette*

    It goes without saying, but please provide an update. It is safe to say we are all legitimatly concerned about you.

  81. Sylvan*

    Please leave.

    Please don’t travel with this person. Don’t go to his house, don’t go to his meeting in another city, definitely don’t fly anywhere.

    You can probably expect him to get real fuckin weird for at least a little while after you leave. Lock down your social media, get ready for some manipulative calls/voicemails, and consider the possibility of him showing up at your house.

  82. KofSharp*

    Run. Don’t be in closed rooms with him. Get out.
    Update LinkedIn and mark it as “Open To Work” and you can choose whether you want recruiters to be the only ones to see or your whole network. But this is terrifying.

  83. Susie*

    Agree with everyone else, you have got to get out as soon as possible. I’m an EA and have never had interactions like this with my boss. I would do whatever is necessary to get out of going on anymore trips with him. Talk to your spouse about what’s possible if you need to quit without another job lined up for safety reasons. This is actually very scary and sound extremely dangerous for you .

  84. Nea*

    OP,

    Taking away things that are personally important to you is textbook abuse. He’s taken your time, he’s taken your energy, and now he wants to take away your very own induction ceremony.

    Run like the wind, and if you can get your own personal records out of HR, do so. If you can’t, see if you can change your home address to some empty lot and get a new phone. This man is dangerous! Emotional abuse is the first step to physical abuse!

  86. iglwif*

    CODE RED. Run away fast, run away far. Holy cow.

    I’m not usually a “quit even if you have nothing else lined up” person but this is WILDLY weird and scary and if you were my kid, my friend, or one of my nieces, I would be hollering at you to get out of there and offering you a place to stay if you needed to get away from this guy.

    1. Lexi Lynn*

      I really want to connect this EA with the EA from the picky travel expense/ guacamole letter or the one from the punished for picking boss up at airport at midnight letter so that they can hear how a good boss acts.

  87. NotAnotherOne*

    All the commenters here put it perfectly but I’ll just echo everyone and say get out now! If you can manage it financially, quit now even if you don’t have anything lined up. If you’re going to put in a 2 week notice, do it in writing and make a copy for your own personal records. Before you quit, make sure you take anything of yours out of that office first.

    Also, if you haven’t done so already, tell your spouse and a couple trusted friends what’s going on so others are aware of the situation. Document everything he does. Put a few inexpensive cameras on your property (Ring or something like that).

    OMFG! I never heard of anything so scary, and I’ve had some really bad bosses in my working life. This is not normal and something is really wrong with this CEO. Maybe a domestic violence hotline can assist you as well, since he’s showing very scary/stalkerish behaviors. I think you should call them before you even tell him you’re quitting as they can hopefully advise you on a safe way to inform him.

  88. Ozzie*

    This is definitely the scariest letter I have read on AAM. Please, LW, get out, and do so safely – don’t tell him where you’re going, let close friends or family know what’s going on so they can be aware, etc.

    Please let the chorus here ring beneath Alison’s advice. This is not normal, and you need to leave.

  89. BigHairNoHeart*

    OP, please use the severity of the response and comments to your letter as a wake up call. It’s incredible to me that you’ve been soldiering through all of this, but you don’t need to forever! If it’s possible to leave right now, even without anything lined up, seriously consider doing it.

    If you can’t, update the resume and start applying to jobs immediately and put whatever boundaries into place with the CEO that you can while you’re still there. At the top of your post, you mentioned that your boss wasn’t happy about how much time the CEO spent chatting with you. Is that person still your boss? If you have anyone in the hierarchy between you and the CEO and you trust them at all, consider asking for their help setting those boundaries I mentioned above.

    Finally, no matter what you decide to do, consider talking to a therapist about this situation. Your boss is screwing with your perceptions of professionalism, subjecting to an absolutely wild amount of emotional labor, alienating you from others, and making you miserable! You deserve the opportunity to talk to a professional about this–they can give you a reality check, help you establish solid boundaries, and help you untangle the really complicated feelings you’re having. I saw a therapist when I was trying to leave my toxic old job and it was the single best thing I did for myself at that time. I can’t tell you how helpful it was.

    Please keep us posted on what happens, and know that everyone reading this is on your side and wishing for the best for you!

  90. Falling Diphthong*

    Many decades ago, I had a social studies teacher who spent an entire class period telling us about a dream he had the night before. And then we still had to do social studies homework afterward.

    Which is to say, I think some people are driven to find a role where they can have a captive audience.

    CEO might intend nothing nefarious, and “just” need a captive audience, while also viewing himself as a life coach who will guide his underlings’ development both professional and personal. Even this least-nefarious take is a huge red flag and reason to find a more normal workplace, where taking care of your boss means you make the airplane reservations for her trip, and you know what does and doesn’t matter to her on those.

    1. Irish Teacher.*

      That reminds me of a teacher I had who once started telling us about how she hoped she hadn’t been talking in her sleep one night because she was dreaming about an ex-boyfriend and didn’t want her husband hearing what they were doing. Yeah, she told this to a class of 16-18 year olds, last year in school, but still vastly inappropriate and…not the only way she overshot a few boundary lines either.

      Nothing to compare with the LW’s situation and nothing that made me feel in any kind of harm (although if I’d needed her subject for my exams, I would have been pretty annoyed at how much time she wasted telling us about her kids and questioning us on what activities would be available to them when they were our age that would be SAFE and showing us her wedding photos and so on – we do seven subjects and only the grades of our six best are counted…now that I think of it, it may not be just my finding that subject difficult that made me full sure her subject would be, and was, the seventh).

      1. quill*

        That’s much creepier than the substitute who used class as a test audience for his banjo playing / stand up comedy / attempts at rap when even a rap put out by Kidz Bop was ‘edgy’

      2. zutara*

        I had an English teacher in high school that gave us a super sketchy assignment. I only remembered this story recently and I’m so glad I trusted my gut that everything about the setup was wrong.

        I don’t recall what the assignment was in relation to or how exactly it was framed, but everyone had to recount a personal story in front of the class about something difficult in their lives. We weren’t allowed to share what we heard in that room that day with anybody. I refused to do it because it felt exploitative and also my classmates were jerks and weren’t owed this kind of vulnerability. The teacher, who up until that point had always been cordial with me, became so mad. I don’t know how else to describe it, his whole face darkened. I and another person who didn’t want to do the assignment got sent to another classroom for that period. Because we weren’t offering our stories, we weren’t allowed to hear anyone else’s. I later heard people were sharing stuff about suicides, deaths of loved ones, dark shit that shouldn’t have been discussed in a public high school classroom but in therapy, instead. I have no idea what it was supposed to achieve, but even then, I knew it was bad news that a teacher spent years collecting his students’ trauma.

    2. Observer*

      CEO might intend nothing nefarious, and “just” need a captive audience, while also viewing himself as a life coach who will guide his underlings’ development both professional and personal.

      He needs SUCH a captive audience that he is insisting that she take an unnecessary trip with him instead of attending something important to her? SO captive that he takes up hours of her time, including unpaid time, and sucks so much energy that she doesn’t have energy for her marriage?

      That *IS* nefarious. Vampire level nefarious.

  91. Nea*

    I’m very sorry to say this, but take a taxi or friend’s car to/from your induction and have a big friend/bodyguard with you. CEO knows where you plan to be and what your car looks like. Abusers get the most violent when their victims run.

    1. Insert Clever Name Here*

      I would also add to let the organizers know you have a stalker and give them a photo of your boss.

  92. this feels too familiar*

    OP, I’ve dealt with someone similar (in personal life, not professional). Dude is deeply fked up. Probably sees himself as a darkly romantic tormented main character. You cannot teach him to stop seeing life as a g.d. Anne Rice novel. You cannot make this situation any better. Please, please get out.

    Talk to your spouse about quitting without notice, with no job lined up. When asked by future interviewers about why you have no reference and a job gap, your line is, “My boss took it badly when I left suddenly due to a health emergency which is since resolved.”

    I’d also recommend a few sessions with a therapist. You may need to recalibrate your sense of what normal/healthy interpersonal relations look like. A therapist can also help you learn to recognize warning signs that someone is targeting you (to clarify: it is not your fault this guy targeted you).

    Please, take it from this internet stranger who’s seen too much: this has the potential to haunt you. I dealt with most of it, tucked the rest away. A nuclear sarcophagus for my mind’s attic, carelessly forgotten in a dusty corner. Worked great, til it started to leak. Get out now, and get help to process everything that’s happened.

    1. Esmae*

      Seconding the recommendation for a therapist. I worked for someone like this when I was much younger, and it took me years to untangle the damage it did psychologically. Even though I knew my former boss was an abusive jerk, my sense of what was normal was completely thrown off, and I had a hard time adjusting to healthier work environments.

    2. Observer*

      A therapist can also help you learn to recognize warning signs that someone is targeting you (to clarify: it is not your fault this guy targeted you).

      In fact, that last parenthetical is another thing a therapist can help you with. Because as your norms re-calibrate you may find yourself wondering how you didn’t realize what a creep this guy is. Or you may have people telling you how THEY would have acted so “perfectly”. And that can be very, very difficult to deal with.

    1. Oakwood*

      Exactly like NXIVM. HBO has a good documentary on NXIVM (The Vow). The LW should watch it.

      Your boss and the NXIVM cult leader sound like they were cut out of the same piece of cloth.

      The NXIVM guy eventually got the women so brainwashed and confused that they thought branding themselves would be a good idea. Even the married women were sleeping with him and taking vows of obedience.

      And don’t say “it could never happen to me; I could never be that gullible”. The one thing that struck me most from this documentary was how normal everyone was. They weren’t crazy, fringe people who couldn’t cope with life. They were normal, often very successful people with stable lives.

      You’re married. You stated this is damaging your marriage. Talk to your spouse and get them involved. This is the kind of thing you and your spouse should be solving together. Don’t cut them out.

      1. Observer*

        Talk to your spouse and get them involved. This is the kind of thing you and your spouse should be solving together. Don’t cut them out.

        This, 1,000x over!

  94. Age of the Geek, Baby*

    OP, my unsolicited advice is this: take your vacation time and use it to deprogram yourself/be there for your partner AND apply for jobs. The more time you can take “off” and away from your CEO, the more distance you can put between yourself in this situation and see how unhealthy it is.

    Bonus points if you can take the time so that it “happens” to fall on the week of your ceremony.

    Get out as soon as you can and godspeed.

  95. The Crowening*

    I’ve seen a few commenters mention cameras around the house. For whatever it’s worth, the Blink outdoor cameras from Amazon work really well, are easy to install, and don’t cost arms and legs.

  96. ecnaseener*

    (I agree with everyone: get out ASAP)
    But where is your actual boss in all of this?? Unless you skipped it in the sequence of events, it doesn’t sound like you ever even got officially promoted to executive assistant….the CEO just snatched you up and your current boss let him?!

    1. anonforthis*

      It’s possible that OP is the lone assistant. Usually non profit leaders just have one admin.

  97. Observer*

    OP, this is one of these situations where I’m going to say, you are better of leaving with no job than staying here.

    At minimum, REFUSE to go on this trip. If he fires you over this, so be it. The ONLY thing I would do first is talk to your spouse. Make sure that your spouse is aware – in excruciating detail if necessary – of how your boss is abusing you. And make no mistake, it IS abuse. And flag that you are going to 1. Refuse this trip 2. Stop taking his calls before and after work hours 3. Stop working excessive hours.

    Document what has been going on. There are two reasons for this. One is that what you describe is so bizarre that there are likely to be times when you question yourself. Your notes will keep that at bay. Secondly, you are going to want to try to collect unemployment if you don’t find a job quickly, and you are going to want to show that you got fired for not bowing to unreasonable work conditions. That won’t help in every state, but in a lot of states if you get fired under these circumstances, you’ll be eligible.

    I don’t make this suggestion lightly. But neither does Alison start her answers the way she did to you lightly. This guy is scary.

    And, if he is calling on your cell phone, you may want to consider getting a new phone with a new number, and leave your current phone on DND except when you are clocked in. The day you leave is the day you cancel that number.

  98. exexecasst*

    I could have written this myself. Please get out now. I had to seek therapy because I stayed in a similarly abusive CEO/assistant relationship for many years. It contributed to all sorts of pitfalls in my life, almost dissolved my marriage, cost my time with my family members I can never get back, and has scarred my both professionally and emotionally.

    GET OUT. It’s not normal. It’s not fair. And no one is going to fault you for leaving. I imagine many of your coworkers can see the writing on the wall and feel that they can’t say anything directly to you about it because of your close relationship to the CEO. Anecdotally, “my” CEO’s business partner tried to get me reassigned to another executive and the CEO ended up not only reversing that decision but buying his partner out. He will truly trap you until you suffocate, and the worst part is once you’re all “used up”… he’ll just turn to the next fresh blooded, unsuspectiny exec asst to suck them dry and not give you a second thought.

    I’m sure I’m projecting a bit but probably not much. I empathize with you and encourage you to please leave.

  99. stelmselms*

    When you can leave, leave that day without notice. Do not give him any opportunity to convince you that he needs you, he can’t live without you, etc. If you can get all of your personal belongings out of the office without him noticing, do that. I would give him notice in writing via your work email and do not come back to the office. If you have to come back in to pick up a last paycheck, etc. have someone with you.

  100. yup*

    No seriously OP, get out before Keith Morrison wants to interview you. None of what you’ve described falls into anyone’s description of normal or even just a bit weird. This is really unsettling to hear about, I can’t even imagine how concerned your colleagues are.

  102. Talula Does the Hula From Hawaii*

    In normal circumstances you would look for another job and leave once you have a start date but in this case I highly recommend leaving today without another job lined up.

    Its that serious.

  103. I'm Done*

    Get out now. Take all evidence of your bosses behavior with you before you leave. If you haven’t adequately looped in your spouse and friends, do so now. Do not give two weeks notice. Email him after you leave for the last time and tell him that you quit and for him to never contact you again. His behavior is so concerning that I worry that he will escalate it if you give him any opportunity. You might be in real danger. Change your email address, your phone number and block him on all online accounts.
    I’m not an expert, but I would think in cases like these you would be eligible for unemployment.
    Good luck to you.

  104. WFH with Cat*

    This is a terrifying situation. Stalker/predator level terrifying.

    OP, nothing about this CEO is normal. I would not be a bit surprised to learn that he has harassed, stalked, abused, or assaulted other women. Please get as far away from him as you can, as fast as you can. In the meantime, take all of the good advise that has been offered: Loop in your husband and friends; set boundaries; and take measures to protect yourself physically as well as mentally.

    Good luck and godspeed.

  105. Juli G.*

    Everyone is giving great advice on leaving the situation.

    I do have some future advice once you’re out of this situation. Find someone who you can trust to help you reset your professional norms. Based on a few things, I think yours have been skewed and I want you to be safe and successful going forward.

  106. JustA___*

    Just wanted to add that once you’re out safely, you should consider seeing a counselor if/once you have the means. Marriage counseling might be good, and I think has been mentioned. But individual counseling because working for this CEO will have WARPED your ideas of what is and is not normal. I came out of a toxic office (luckily my boss was just interested in exploiting workers, not stalking them) two years ago, started therapy 6 months ago, and I’m still unpacking some of it–and again, nothing so frightening for me as what you’re going through.

    I’ll skip the “get out” bit and the “prioritize your safety” bit, since so much of the commentariat has that covered. We’re pulling for you, LW.

    1. Teekanne aus Schokolade*

      YES! It took me SO much therapy to relearn norms again after my bad-boss made me think everything was my fault, and I was not to trust anyone but her. Agree completely!!

    2. Ozzie*

      Yes agreed here! I often have to stare directly at things I’ve learned in toxic workplaces and remind myself they’re not normal. This is years after the fact. (and none were terribly major, just your typical Bad Workplace things) If therapy is realistic, I second (third? fourth?) this!

  107. redflagday701*

    I am scared for OP and honestly for her husband too. (And discovering he existed was quite a way to close out this letter.)

    1. Liz T*

      I’m really worried for OP, and worried that even if they leave they’ll try to be “professional” and stick give a long notice period and give the CEO a chance to do something awful :(

  108. bluephone*

    I was wondering what Christian Grey was up to lately and I guess he’s still working :-/ (and looking for people to isolate and exploit, gross)

  109. Teekanne aus Schokolade*

    OP, I could have written this letter just a few years ago. Take hard copies of everything. My boss threatened to have cops escort me out of the country when I quit because of so many of her similar, freakish behaviors. I couldn’t be her pet any longer, or her all-in-all, or the one who covered her illegal activities. All I did was say I wasn’t comfortable working for her any longer and she FLIPPED. Please be careful, call a lawyer, and be prepared.

  110. RagingADHD*

    Longtime exec assistant. Nope, nope, nope.

    The exec assistant / PA pays attention to and anticipates needs for the exec AT WORK. There will be some spillover in helping with personal tasks, but it’s stuff like picking up dry cleaning, making haircut appointments, mailing off insurance paperwork, that kind of thing. Not therapy or a relationship stand-in for a romantic partner.

    This is gross and wierd in every way. There are people who choose to be paid escorts. He can hire one of them if he wants, on his own dime.

    I do wish, though, that people would stop using the word “grooming” inappropriately. The LW is obviously an independent adult without any cognitive disabilities. This is icky and overstepping, but every “frog in boiling water” scenario is not grooming.

    The term is being misused, politicized, and diluted these days in ways that hinder victims of CSA from being believed and helped.

    1. Cthulhu's Librarian*

      Please don’t recommend that hiring escorts is appropriate for someone with the levels of dysfunction this boss is showing. Sex workers are humans as well, and should not be put in unsafe positions dealing with abusive and unstable individuals because off their profession, any more than anyone else.

      1. RagingADHD*

        I’m not recommending the boss do anything. The boss didn’t write in for advice.

        However, if he were asking an escort to accompany him on trips, for example, it would not be inappropriate. It would be a reasonable service to negotiate in that context. And, as a contract worker with a clientele instead of an employee of the firm dependent on a single job, an escort would have far more freedom to decline if they didn’t want the gig.

        If he were asking a romantic partner personal questions about their childhood, that would not be inappropriate in context. It’s a normal thing to do in an intimate relationship- not an employment relationship.

        If he were asking a therapist (or even a close friend) for emotional support, that would not be inappropriate in context.

        The boss’s behavior is problematic precisely because he is demanding the LW act in roles inappropriate to a boss/employee relationship.

    2. Observer*

      Grooming does not only apply to children or people with cognitive issues. It DOES refer to positions where there is a power differential and where the more powerful person uses an apparently reasonable / normal relationship as the entree to start and continue the process.

  111. Guin*

    I will reiterate GET OUT GET OUT GET OUT, and add: if you are compelled to go back to the office to get personal items, bring a LARGE SCARY friend with you (or your spouse, if they are large and scary.) Does the building have security guards? Ask one of them to accompany you, as a witness. Also, don’t worry about getting a new job. Executive search/temp firms will be swarming you immediately. I repeat: GET OUT.

  112. Excel-sior*

    I’d like to add my voice to the chorus of “get out”‘s. As soon as you can. I’d also suggest that if it’s at all possible, find somewhere else to stay, either permanently or temporarily.

  114. yala*

    No thoughts, just screams.

    Well, one thought:

    If you can, maybe speak to an employment lawyer before leaving. It’s likely your boss will try to retaliate in some way, and having someone in your corner who knows the score before that happens could be a huge help.

    Be safe. Get out soon.

    1. Typing All The Time*

      Yes. Consider also a cease and desist letter if he contacts you after you leave.

  115. Adds*

    This is The Most Terrifying Thing I’ve ever read on this site. And it’s an abridged account!

    LW please be safe and leave as soon as you possibly can. If you and your family can survive without you having something lined up to go to immediately, leave that banana crackers job Now.

    I also echo the folks saying to let the chorus of the comments help reinforce that your feelings of unease in this situation are absolutely correct and not to dismiss them.

    1. Teekanne aus Schokolade*

      This is what I was thinking! Nobody even mentioned worst boss award Winner because they’re all genuinely worried for the OP’s safety and sanity.

  116. Wendy Darling*

    I felt a bit ill reading this and appreciate the number of people who’ve said get out. I worked for this guy (or someone so much like him). When I read “His statement that he waited for years before you came along and he chose you – it sounded to me like a version of lovebombing. Even the tactic of asking deeply personal questions about your childhood, asking you to hold nothing back. Did you say that or am I just inferring my own experience – at this point IDK. I digress. I’m definitely feeling some shame and regret at not seeing it sooner. It’s over now thank the universe.

    Luckily you are in a headspace to question his awful, misogynistic, potentially narcisistic abusive behaviour whereas I was not. Nothing this “CEO” is doing or saying to you is remotely acceptable. There has to be a line between work and personal lives – this dude is crossing them hard.

    I didn’t see what was happening when it was happening. I was a depressed, close to suicidal, alcoholic; desperate for any form of kindness, love, and attention. It took 2 years for my life to implode, 2 years to surface get out, and another 18 months to cut this person off and out of my life.

  118. merida*

    Yuck, I’m so sorry you have to deal with this, OP! I’m going to be the devil’s advocate for a second. Let’s say for argument’s sake that the CEO isn’t actually being creepy (which he definitely is!) and that somehow what he expects is reasonable (it is not, but…) – even then, if somehow you worked a healthier job and had a professionally normal boss, if you’re miserable in a job, why would you stay? I can see why you’re miserable; it sounds entirely awful. But if you don’t think CEO is being creepy and don’t want to leave because of a creep/safety factor, then leave because you deserve a job that is better for your mental health. You deserve to be safe at work AND you deserve to not be miserable!

  119. Scared for LW*

    I cannot properly articulate how much danger LW is in. In all seriousness, those trips are leading up to “LW goes missing on business trip. Family asking authorities for help”, after she rejects an inevitable sexual advance.

    LW, please run far. Run fast.

    1. Gary Patterson's Cat*

      Ok, well I hadn’t gone THAT far. I do know of EA’s going on (or going ahead) on business trips at the CEO level.
      I normally would not think that ask as being alarming itself, but combined with all the other STUFF unpacked here, it does read as leading up to something to force the intimacy.

      This letter almost reads like a bad 50’s or 60’s movie plot where that kind of thing was unfortunately far more common.

  120. Run Run Run*

    That you had to ASK whether the CEO’s behavior was abnormal speaks to the fact that he has already warped your thinking. This is what abusive people do. They’re not “abusive,” they say; you’re “too sensitive.”
    As everyone says, quit today. Don’t allow any contact from the CEO; he will try to manipulate you and make you doubt yourself. He’s obviously good at that, because you haven’t quit yet.
    Next thing to do is start seeing a therapist immediately. You will need help to untangle this so you never find yourself in such a situation again.
    Hang in there. The AAM community is pulling for you!

    1. Gary Patterson's Cat*

      It sounds like the LW is fairly young and maybe this was a first or second professional job.
      It’s a shame because they’ve been exposed to situations that are so not the normal business world. They will need help seeing that this is not the way a healthy organization should work.

  121. L Dubb*

    OP, please talk to a domestic violence advocate. (Or a therapist with experience in DV.) There have been a ton of great tips mentioned in here about keeping yourself safe, but you are going to need ongoing support after you’ve quit with how to handle his retaliation. And really, you’re going to need a plan before you quit, and a DV advocate can help you with all of that.

      1. Working Hypothesis*

        Me too… but I wouldn’t read it at bedtime. It would probably give me nightmares.

  123. Gary Patterson's Cat*

    This has to be one of the strangest letters I’ve read on here (aside from the Duck Club).
    No, deal LW, none of this is normal business or CEO/Employee behavior. But I think you know that.

    Sure, there are many CEO’s who have demanding needs and requirements from the executive assistants. I have heard of some EA’s actually becoming more like personal assistants, with tasks that included booking travel for the CEO’s kids and family, running errands, arranging real estate sales or moves and vacations, etc. Certainly some EA’s do go on business trips to take notes or file paperwork. While not exactly the function of a EA, sometimes these things nevertheless might still be within the realm of work duties at some places.

    Your CEO is asking for much more PERSONAL engagement. Moreover, when you try to put some boundaries back IN place, they are balking and trying to take more control over your life. Your CEO needs something (perhaps it’s sexual, but could be emotional) but whatever that is it is not a work something! And this is inappropriate and controlling behavior from him in every manner.

    I feel almost like you’re in a bad movie like Two Weeks Notice or and episode of Mad Men and you’re Peggy helping a drunk Don Draper deal with his emotional baggage. Please get out of this company. I would try to be professional and give notice, but with someone like your CEO, that may be hard to do. Without a doubt, he’s likely turn on you when you give notice, so be prepared and have other references, resources and funds lined up.
    I think most of us here are worried for you. I hope it’s not at bad as we’re thinking.

  124. theletter*

    Another red flag is just the lack of time the CEO is spent working.

    Being boss doesn’t mean you can delegate work to go play golf, it means you have to delegate work in order to take the big stakeholder out golfing with the specific goal of getting them to re-sign the contract and if the golf trip fails the CEO will have to spend the next month hunting down a new stakeholder of size or the whole compay will implode so the CEO needs her calendar cleared the day before to memorize KPIs and that means no emergencies so someone else will have to calm Karen down when the server sparks.

    So no, a CEO shouldn’t have time for hours of mutual therapy sessions, not if they’re functioning well in their job.

    1. Gary Patterson's Cat*

      I can’t even imagine the state of this company with this CEO at the helm.
      I have some mental picture of this CEO being like also some tech founder or something. Like Elon Musk type Svengali or something.

  125. IT geeks against creeps*

    OP we believe you, and you have been brave and smart to ask is this normal. As everyone has said so eloquently: NO IT IS NOT, it is time to leave, and we are all worried for your safety.

    You have already been given much excellent advice about things you can do after you leave to shut down his inevitable stalking and to better protect you. (Echoing “The Gift Of Fear” – yes it has flaws, but it may help save your life.)

    There are also things you may be able to do before you leave:

    – get a new (personal) email address now
    – get a new virtual phone number (e.g. Google Voice – it acts like a cell number and forwards to your real number)
    – get some kind of mail service, these are often cheaper and faster than post office boxes and will forward to you
    – update your HR records to replace your current details with the above, this may reduce how he can find or reach you if he hasn’t thought to already save them; many HR systems won’t keep an audit trail of previous details
    – if your phone is owned by work, figure out how to copy its contents before handing it back
    – also consider dumping every email he has sent you; they can see if you forward it to another email but you may be able to export to a thumb drive, or print to PDF and put those on a thumb drive (these may be prohibited by your workplace policies or locked down by IT)

    I also suggest assuming that all of your devices are now infected with stalkerware. The Coalition Against Stalkerware has a great resource here for detection, removal, and prevention.

    This may seem overwhelming and I do not want you to delay getting out to try to achieve these tasks. If you are already delaying for other reasons then some of these may be helpful. We all urge you to get out and assume the worst of him. The asymmetry of power is so extreme here. We worry for your safety, we believe you, and you did the right thing in asking the question.

    1. Observer*

      update your HR records to replace your current details with the above, this may reduce how he can find or reach you if he hasn’t thought to already save them; many HR systems won’t keep an audit trail of previous details

      Nope, don’t update HR records. Instead use these new numbers and mailing addresses as your primary ways to be reached by everyone other than boss. And the day you walk out, you turn off the current number and personal email address that you have. Because there is no doubt that CreepyBoss already has the existing number and email address. You need to create new access points that he DOES NOT KNOW ABOUT.

      if your phone is owned by work, figure out how to copy its contents before handing it back

      If your phone is used by work, get rid of EVERYTHING remotely personal on it. If there is anything you want to back up, there are tons of resources for how to do this. Do that TODAY and NEVER use that phone for ANYTHING personal again. And, never take that phone with you ANYWHERE unless you are clocked in.

      When you quit, wipe the phone if you can. If you can’t go to IT BEFORE you tell your boss that you quit and ask them to reset your phone because you are having intermittent problems, and this would be the fastest way to fix them. If you can’t do even that, them manage to drop your phone into dirty water or maybe spill something like coke all over it and take a few minutes till you “realize” and wipe it off. Because there is a real possibility that your boss may have put a hidden tracker or logger on your phone.

      I also suggest assuming that all of your devices are now infected with stalkerware. The Coalition Against Stalkerware has a great resource here for detection, removal, and prevention.

      Yes. Unfortunately, this is EXTREMELY likely.

      1. IT geeks against creeps*

        On reflection I support these refinements or disagreements 100%. These are better answers than my first advice. Nicely done, Observer.

        OP and anyone else in a similar position: there are many good resources to help you do all these things, and many people here who will help.

  126. publicsectorprincess*

    NONE OF THIS IS YOUR FAULT. Please remind yourself of that. Accepting a job, being friendly, taking this person’s phone calls, whatever else has transpired does not mean you deserve this or bear any responsibility for this situation. The commenters telling you to get counseling are giving you excellent advice. You will need to process this with a professional.

    This CEO is likely to try to convince you that you share responsibility for this situation, will try to cause you to doubt yourself. Because this is what abusers do. It is one of the reasons it can be so hard to get help or even acknowledge how wrong a situation is. Its a really good reason to quit via email and cut off communication.

    Some of the things being suggested might seems a little excessive, like getting a new phone number/address. . .but it is better to feel a little silly and like you overreacted, but be safe.
    The reason people are making those suggestions is because this behavior is very concerning, people pointing out the domestic violence parallels are very much on point. The potential for violence or disruption of your personal life is very real and extremely likely when this person feels their control is threatened. Take precautions.

    This is an abusive situation, and it is not your fault. Take care, get out, get help.

  127. BorisTheGrump*

    OP, I just want to say I hope you’re reading these comments and I hope you know we support you.

  128. GOOD TIMES*

    It sounds like your boss is confusing an Executive Assistant with a Personal Assistant or something. Had a friend who was a “personal assistant” to a celebrity and she said it was emotionally exhausting, she was most definitely expected to live and breathe the celebrity and provide emotional caretaking and long personal phone calls, etc.

    However, she knew that was the job going in and even so, she only lasted a short time because of it.

    Either way, there does seem like something wrong with your boss and I tend to agree you shouldn’t spend another day working for him.

    1. Gary Patterson's Cat*

      Truly, emotional care taking is not even the job of a personal assistant! They are to help you manage and organize your life to free your time–not help live your life. An Exec Assistant is to help you with all the pesky work details, documentation and paperwork so that you can focus on managing the company more effectively.

      But it sounds like this CEO does very little managing of the company. I can’t even imagine the state of this company if the CEO is like this!

    2. Observer*

      It sounds like your boss is confusing an Executive Assistant with a Personal Assistant or something.

      Even Personal Assistants don’t do this kind of stuff.

  129. File Herder*

    1) Run.
    2) THIS MAN MAY BE READING AAM AND RECOGNISE THIS. It happened once on Captain Awkward. Do not be anywhere alone with this man without someone else in shouting distance, because he may already be aware of hundreds of comments telling you to get out now. Be prepared to literally run. It probably won’t happen, but you have to be prepared for the possibility.

    1. zutara*

      I didn’t know about #2. Was the LW in that instance ok after being found? Do you remember which letter it was?

      1. File Herder*

        Friend in that one rather than a work relationship. I can’t remember when it was, but it must have been a while back because it was when comments were still normally open. Hidden cameras were found, including in the house of LW’s family, not just in hers. Partner was not convinced that they needed to go to the police because it was their friend (commentariat was very much convinced they should). Then the Captain closed the thread, because apparently friend had found the thread, recognised himself, and was using the information in the thread to his own benefit. I don’t know if there were ever any updates, and I would not have wanted to see one unless it was “friend is now in gaol and will be staying there for the forseeable future”, because of the danger any more information could have been useful to him.

        1. zutara*

          I remember that letter! Wow, that’s like, one of the worst possible outcomes of that situation. I also hope the LW ended up safe from them.

          1. Not Your Secretary*

            Was it this letter (which is what came up when I searched the CA site for “hidden cameras)?”

            #936: “My best friend’s partner secretly records his guests while they are in the bathroom.”

            It doesn’t quite match what File Herder was saying, so I might have it wrong! I went through a similar situation years ago that never got resolved to my satisfaction, so I’d really like to see how it went down for others.

              1. Not Your Secretary*

                Thanks for the quick reply! I just started going through the mounds of comments there, looking to find the part where the perv found the post and began using it to his advantage. It’s not the exact situation I lived through, but close enough that I feel like my stalker and Captain Awkward Perv might’ve had the same playbook, and I want to examine those moves for future reference.

  130. Lobsterman*

    OP, your safety is at risk, and you must quit now and take the actions discussed above to protect yourself.

  131. Massive Dynamic*

    HOOO BOY OP. So many good ideas upthread here, and I’d like to add one. If you know the BOD, tell the BOD. Probably not until you are ready to pull the trigger on disappearing into the night. Send an email to any board members that you know, doesn’t have to be too long just an FYI that CEO is obsessive and you’ve made plans to leave and you fear for your safety. Then leave!

    Best of luck to you and your husband here. I’d board any housecats or other at-home pets for a weekend or so too…

  132. anonforthis*

    In addition to what Alison said, the part about “he waited years for someone to come along” jumped out at me as a very familiar manipulation tool I’ve experienced myself. It’s super common for people trying to rope you into a codependent relationship to make it seem like you are The ONLY One for them, that you are special, that they are would not have found what they were looking for if not for you… Yeah don’t fall for it. It worked for me in an abusive relationship when I was very young, with low self esteem and desperation for validation.

    Also, the fact that you feel uncomfortable is evidence enough that this is Wrong Wrong Wrong.

  133. A Feast of Fools*

    “I would rather attend an induction ceremony to an honor society I was just invited to join.”

    If OP is a normal-aged college student (vs an older, “non-traditional” student, like I was in my 40’s), then this just got a lot grosser. The CEO is preying on someone who he knows is inexperienced in the work force and who is likely a couple of decades younger than he is.

    He’s grooming a younger person because he knows she doesn’t have the work experience to know that what he’s doing is blatantly wrong.

    1. Sharpiee*

      I’d like to add that if OP is a younger person, she should know that even older people get manipulated into these types of “relationships”. She is far from being the only one and she shouldn’t feel ashamed or embarrassed. Victims often blame themselves for not seeing these people for what they were from the beginning. We’re simply not taught that there are people like this out there and don’t recognize that anything is off until things start blinking red.

      The ONLY remotely positive thing that emerges from the ashes of these situations is that going forward you can spot these dysfunctional people a mile away and know to stay away from them. I agree with others’ suggestions that OP starts working with a therapist who can help her work through this.

  134. Cake or Death?*

    “In July of 2020, I was approached by the CEO to undergo “career counseling” and he would be my mentor. We had one very strange meeting in which he spoke a lot about brutal honesty, holding nothing back, and advised me that this would be a painful but necessary process, while asking very personal questions about my childhood and family.”

    WTAF!!!!!!!!!!!!!!!!

    “We had one very strange meeting in which he spoke a lot about brutal honesty, holding nothing back, ” …this sounds like he was getting ready to tell her how attracted he was to her.

    SHUDDER. TOTAL creeper vibe.

  135. File Herder*

    Okay. Longer comment. As others have already said, if you can do so safely, document. Any of this that’s in writing, copy it and put it somewhere he doesn’t have access and the company doesn’t have access. Make notes while it’s fresh in your mind, with dates if possible – your work diary may help with that, so try to look at that while you still have safe access. If you don’t have exact dates, a rough timeline will do. In the UK this is called a Scott Schedule if you want to take it to an Employment Tribunal. There’ll be something similar in the US. It will be useful even if you just need to prove that you had no choice but to walk when you’re applying for unemployment benefit, and you don’t want to take legal action. As often said on this site, even if you don’t want to take legal action it’s worth talking to an employment lawyer to see what your options are, including applying for unemployment benefit.

    You cannot continue to work for this man. Even if it is safe to continue working while you get things in order so that you can leave, you must start making those preparations, and you must be prepared to leave immediately if things go pear-shaped.

  136. I've Escaped Cubicle Land*

    OP, When you do get out, please please update. I want to hear all about your happy new job and reassurances that you are safe.

  137. Anita Brake*

    No, no, no…NONE of this is remotely normal or OK. You need to GET OUT NOW. Or as soon as is even slightly possible. He is grooming you and you are not safe.

  138. Forty Years in the Hole*

    Tomorrow is “Administrative Professionals” Day…I would be curious for what the CEO has in mind O.o
    OP – can you GlassDoor this guy? Good luck breaking free.

  139. NeedRain47*

    I’m just gonna reiterate how important it is to not talk to him after you leave, OP. People like this take any contact at all as encouragement, as a sign that you will let them back in if they just persist. So if any of this makes you feel like you’re being mean… well, you’re not. Cut him off and don’t give an inch. You’ll be so relieved later.

  141. Wombats and Tequila*

    What would happen if you just started setting hard limits with this guy? “No, I’m not going on the trip with you on X weekend. I have plans.” Then stop discussing it with him. Quit when it is quitting time. Turn off your cell phone or block his calls. What’s the worst that could happen? He fires you and you get your personal life back, plus unemployment?

    1. Esprit de l'escalier*

      Yes, this. Don’t let him dictate the terms of your life outside the scope of your work responsibilities. (And as Alison said, most of what you’ve reported is waaay outside that scope.) Him firing you would be a great gift to you, if he did that before you left on your own, although he would undoubtedly claim it was about your job performance, so you need to be prepared with your own documentation.

  142. 6 o'clock farmer*

    Oh my god, LW… run! Get as much evidence of inappropriate communication for your records, consult a lawyer just in case, and quit without notice ASAP. This is a very scary sounding situation, and I really hope you’re able to get out now and stay away from this creep for the rest of your life. Good luck!!!

  143. Office Ninja*

    THIS. IS. NOT. OK.
    I have been working as an EA for 6.5 years for the same company and the same boss. Obviously, my relationship with Bossman has changed over 6.5 years. But it has always been professional. We can make jokes and my relationship with him is entirely different than any other relationship either he or I have with anyone else in the company.
    Being an EA is about mutual respect for each other.

  144. Hannah Gokie*

    I think we have a contender for “worst boss of 2022” already. Holy shoot. Get out of there, OP. ASAP.

  145. I was in a similar situation*

    Wow, people are really freaked out by this situation, OP! But I found it very familiar, and I think you’ll be okay.

    I had a boss that made many similar demands (emotional and personal caretaking described as a core job function, no boundaries around “honesty” and sharing, no boundaries around my time or business hours, being told I’m special and how “good we have it” compared to others, too many hours spent talking about non-work subjects or inappropriate work subjects, etc) though not the extreme traveling bit and this exec was female, not male. When I left it was difficult, there was some inappropriate responses, and she did keep trying to get me to return. Looking back now, I was definitely emotionally manipulated and slightly brainwashed by her, but my physical safety was never in danger (other than being in the car with her. She was not an attentive driver). IT’S POSSIBLE that you are in danger, like so many of the other comments suggest. But it’s also possible that a charming and sometimes lovable person, who made you feel competent and special, is treating you like crap, and you should leave because Fuck That Guy and not Run Away Before You End Up The Subject Of A True Crime Podcast.

    I just wanted to share this perspective in case it is helpful.

    1. Critical Rolls*

      This CEO has ticked enough abusive behavior boxes that it’s a disservice to underplay the potential dangers of leaving the situation. We don’t need to take the half-joking comments with pop culture references too seriously/literally, but there are a LOT of red flags for stalking, and potential for a scary blowup over a resignation. Further, as someone who’s been abused for the last two or three years, LW should protect herself from more abuse and manipulation, and that means getting out immediately, with minimal interaction, and strictly managing contact going forward. The advice doesn’t really change between FTG and RABYEUTSOATCP.

    2. Jessie Spano*

      You’re right that danger might not be imminent… but your situation doesn’t exactly translate and the possibility of danger in relationships like this is not insignificant. This is a real listen-to-your-gut moment and not a time to give a “sometimes lovable person” the benefit of the doubt. He hasn’t earned it.

    3. Observer*

      IT’S POSSIBLE that you are in danger, like so many of the other comments suggest.

      No, not “possible” but highly probable. The behavior under discussion is bad enough on its own. But the OP has noted the harm that is ALREADY occurring – she’ miserable and she’s so exhausted that it’s harming her marriage. And now he is trying to force her to turn down something that is important to her!

      All that says that when she leaves, he will NOT behave well. And that he is likely to escalate behavior that is already waaaaay beyond even “overstepping” and actively harmful to the OP.

      Looking back now, I was definitely emotionally manipulated and slightly brainwashed by her, but my physical safety was never in danger

      Physical safety is not the only issue that the OP should be concerned about.

      You do present a perfect example of something that Alison often talks about, and the many commenters have mentioned, though. The fact that you frame being emotionally manipulated and “a bit brainwashed” by your former boss in such a low key manner is pretty jaw dropping. You might very much benefit from taking a step backing and coming to realize just how out of bounds this behavior was. Not to make you feel bad, but to help you avoid such behavior in the future.

    4. Irish Teacher.*

      I think I’d be less concerned about physical harm than harm to the LW’s reputation and so on. I am really questioning whether the LW has the true story about the woman from HR or if that is simply what she was told by the CEO. If it IS a story the CEO make up to isolate the LW (and I admit that is just a guess and I could be totally wrong about that), then he is not above making up very harmful stories about people.

      And while I don’t necessarily think the CEO IS likely to physically harm the LW, I think the main reason people are warning about the possibility of it is that it’s better to be prepared for it and NOT have it happen than be unprepared and have it happen.

      1. Working Hypothesis*

        I think it’s pretty clear that the CEO is likely to try and wreck LW’s professional reputation. As you point out, we’ve seen him do that once already. I would be very interested to hear what the HR person’s got to say about their departure. It’s certainly possible that she really was doing all those terrible things (if only because horrible, creepy, emotionally manipulative bosses sometimes hire horrible, creepy, emotionally manipulative staff, and she could’ve been someone he took on recognizing a kindred spirit), but it’s more likely in my opinion that she did little to nothing wrong and his description of her behavior was simply a blueprint for what this guy does when someone he has latched onto decides to cross him.

        What, if anything, ELSE he may also decide to do is a separate question. I wish I were sanguine that he was “only” going to try and trash LW’s professional reputation and career. But he’s a lot more obsessed with LW than it sounded like he had been with the HR person, and that makes me seriously worried about much greater escalations.

  147. Mad_Bear_Lady*

    Please put your safety and sanity first OP. I don’t know what your circumstances are but you can always get another job. Your marriage and wellbeing are priceless

  148. Goody*

    I knew from the title that I was going to need popcorn and I was snot disappointed.

    OP, please run like the wind. As soon as you are free, block him on EVERYTHING.

  149. LostBoyJim*

    I’m with everyone else on the RUN RUN RUN part. The notes on the HR being fired have more than a hint of gaslighting, as does the “I’m the only one you can trust.” Start documenting now, with dates.

    While this may be overboard, I think it would be a good idea to learn how to get a restraining order before you resign. I also think that in this case a two week notice is not in your best interest, and would considering leaving with no notice.

    This isn’t just creepy, it is manipulative and outright scary.

  150. TiredMama*

    Gah, consider a new phone number, new email address, new home in a new city far from your current city. Document everything. Document what you return to him when you leave. Give him no reason to contact you. Godspeed.

  151. Anita Brake*

    Tell your husband ifi he doesn’t already know what’s going on here, especially the part where the boss is making it so that you do not have time for your marriage. Then get a lawyer. Then leave and don’t go back. Two weeks’ notice is not applicable in a situation like this.

  152. Bill and Heather's Excellent Adventure*

    My CEO talks a lot about the role of an executive assistant, specifically that they are the one person who is focused entirely on the CEO and always has their eyes on them, and that he waited for years before I came along and he chose me.

    DDDDD:

    OP, please take Alison’s advice (and that of the other commenters) and GET OUT because this is some terrifying sh*t. And please, please update us when it’s safe to do so.

  153. Teapot Gnome Scandal*

    Besides the ultimate creep factor I feel at this letter (like everyone else here) there’s still the ultimate horror/mystery of what happened from mid 2020 – early 2022. Can you imagine! This isn’t even everything that happened! Ah, ick, yikes!

    OP along with everyone’s advice about getting out NOW, you are able to set boundaries. If he calls after work – don’t answer, don’t go on the business trip – you have other plans. If he fires you (but unfortunately his creeptasticness sounds like he’d probably manipulate/guilt you rather than just fire you) then that would be great for you. I’m also hoping that most of your interactions with this person have been virtual, besides the business trips which I can’t. even. imagine. what that must be like/how awful that must be. Also, I’m hoping that you’ve let your spouse or maybe someone else close to you know how this has been going. Just as another form of protection/context for how you’ve been feeling lately. This isn’t just normal stressful or crappy work stuff this is creepy, exhausting, unacceptable work stuff.

    Also, as a p.s to add that if you don’t receive pay (say if you give your notice now, before payday or take vacation and then quit and your paycheck is two weeks short) there are probably processes for going to the Labor Board (or something similar) for that pay. Just in case he tries to punish you retroactively. If you worked or had paid time off you deserve to be paid.

  155. Lady Pomona*

    OP, in addition to getting out of there ASAP, please be sure to loop your husband in on just how nutty this CEO is and how untenable your situation there has become. He’s probably already worried about you – he must see how drained you’ve become – and he can (and should) be your best source of support now. Plus, there’s no way around it – your boss sounds so unstable that he could actually become dangerous. Your husband absolutely needs to know exactly what’s going on!

  157. Mr. Bob Dobalina*

    Oh boy. This one gives me a bad feeling. If OP can afford to quit immediately, I would seriously consider that: Don’t go on that trip with the CEO – instead, while he is out of town, resign on a same-day basis. On the other hand, if OP needs the money and must be employed to support the family, then I think a short exit plan must be initiated immediately. OP should send out resumes immediately and try to line up job interviews. OP should start discretely taking home personal belongings, so that when an acceptable job is found, OP will be ready to resign on a same-day basis and quickly exit. If OP can take vacation time, and resign while on vacation, that would work. Best of luck to the OP.

    1. Mr. Bob Dobalina*

      Just to make the point clear: This is one of the rare instances where I would not give 2 weeks notice. No matter what course of action is chosen, the OP should resign on a same-day basis, preferably when the CEO is out of the office or when OP is out of the office. I also agree with the other comments about making sure the husband is aware of everything that is going, and in fact, I would make sure that multiple people in my inner circle were aware.

      1. Mr. Bob Dobalina*

        Also, OP should keep their next job confidential as long as possible. Do not tell co-workers and do not put it on LinkedIn.

  158. Limdood*

    DOCUMENT ALL OF IT!!!

    This is a CEO. He is obsessed with you and undoubtedly had the resources to track you to wherever you go. If that scares you….it should!

    DOCUMENT everything so that IF he gets mega-stalker on you and continues harassment after you leave, that you have ammunition for a lawsuit/restraining order if you need one.

    If you don’t need, well then I wasted your time. Shame on me. If you DO need it and don’t have it, well… Trying to file a restraining order or press charges and failing is going to make him feel untouchable.

    For your sake and your family’s, prepare for the worst.

  159. Chilipepper Attitude*

    I’ve been thinking about the OP all day! Like so many, I’m truly worried for her. Was there an update, is there any way to help beyond posting here?

      1. Working Hypothesis*

        Me too! I know that the commentariat here organized an assistance effort to one LW a long time ago who needed a hand, though I’m not sure how it was done. But if the current LW would like it and there’s a way to make it happen I would be happy to participate.

        To the LW: you need to be free to get out quickly and completely, and do whatever it takes to keep yourself and your family safe. Anything we can do to make that easier?

  160. Anat*

    Many people covered the potential physical danger of this guys retaliating. He may or may not do that, but he will CERTAINLY attempt to retaliate against your career and reputation. Exactly as you’ve seen him do with you HR friend — and probably worse.

    Part of your preparation for leaving needs to be sitting down with a lawyer to discuss your options when (not if) he does this.

    1. Canterlot*

      Very much this. Whether this guy will be a physical threat or a stalking threat is hard to tell at a distance – definitely people are picking up on a real possibility – but whatever the nature of the threat, a lawyer is your friend here. The LW does not need shell out the big bucks to sue, but they should pay for a consult if at all possible as step one in their extraction plan. An attorney can advise you on risks, how to document, your rights, strategies. It is good to have counsel in your corner.

  161. SloanGhost*

    Anyone else’s skin just try to crawl all the way off their body?

    OP, I would approach this as though you are leaving an abusive personal relationship and not just a bad job. Hopefully the extra caution isn’t needed, but I’m not feeling confident that this guy is going to behave reasonably when you “reject” him.

      1. Pdweasel*

        Mine crawled out the window, down the side of the skyscraper I live in, and is making its way towards the Lake. I’m cold.

        1. Working Hypothesis*

          You’ll be even colder when it reaches the lake, bringing all your external never endings with it.

  162. Chickaletta*

    From one EA to another, this is not anything remotely close to normal.

    (side note – how does he have this much time to talk about non-work things during the day???)

  163. Anonosaurus*

    This is a very unsettling letter. Add me to the list of people saying you must get out of this situation. I would treat it as leaving an abusive personal relationship and not quitting a normal job. There’s advice out there on how to make a safety plan for leaving such relationships, and I think it would be wise to do something similar because this individual isn’t going to simply accept your resignation and buy you a going away card. Sometimes when our perceptions of reality have been manipulated by this kind of individual we underreact to things that would cause people on the outside to freak out. Some part of you knew this wasn’t right and that’s why you wrote Alison. Listen to that inner voice.

  164. Molly*

    Please, please, please update us! Multiple updates if you can manage it! We are all worrying about you!
    Also, while I’m aware that this is work and not your home life, it might be worth calling the National Domestic Violence Helpline. They may be able to give good advice on how to extricate yourself as safely as possible.

  165. BasketcaseNZ*

    Before you hand in your notice:
    Clear all your personal items from the office. ALL of them.
    Delete any personal emails off your account and then further, if you can arrange it with IT, off the server.
    Ensure you log out of any personal media – social / email on any work devices. Delete any bookmarks and clear your cache.
    Consider getting a new phone and new number. If you have a work device, factory reset it and ensure you remove any external storage.
    If you are friends with the current HR, can you arrange for your file to be locked so CEO can’t access it?

    This is the kind of person who this could all go bonkers when you tell them you are leaving. Make it as hard as possible for them to do anything to you by being ready to walk out the door with a clear slate behind you.

  166. OhBehave*

    Get the hell out of there! Do NOT feel any guilt about doing this.

    Adding to suggestions:
    Change your address to a P.O. Box if possible. Remove your address with HR. Boss can find it, but make it hard.
    If you have emails backing up what you’re going through, print and take home.

    Please update. We are concerned.

  167. raida7*

    ” and that he waited for years before I came along and he chose me.”
    Dude. That’s not good – this person was waiting for someone like you to come along, to be blessed with the task of focussing on them.
    :|
    What a terrible fcking job description it would be.

  168. Boof*

    I bet he watched too much Avitar and wants you to be Julie to his Verrek
    I doubt you want to be Julie; i doubt most people do

    Set boundaries (no to this trip; no to being accessible outside of work hours; no more than superficial and pleasantly bland personal info from you if anything), stick to them, and start job searching in case that’s not enough for you to be comfortable/ happy with this job

  169. Mrs. Hawiggins*

    Good Gawd GET OUT.

    I am an executive assistant to the CEO of my company. This makes me want to retch – – “as part of the “emotional caretaking” that I am supposed to perform as his executive assistant”

    We do not do this. This is not our job. Your CEO has glommed on to you for reasons other than being his assistant. Please leave as soon as you can and do not leave a forwarding email, phone, or address. Don’t even show up again to that office. Just when I think coworkers and bosses couldn’t get any weirder, this poor OP writes in with a real stunner. We are all concerned for you. Get out get out get out.

  170. Friend in Virginia*

    I agree with all the concerns that have been raised. Additionally, the fact that he asked the “very personal questions about [OP’s] childhood and family” makes me concerned that will use, or is already using, those details to stalk OP. I would suggest giving a heads up to family and friends to watch out for this creep and report to OP if he shows up or contacts them, and to request that any of their social media posts that contains OP be set up private.

  171. Pdweasel*

    Well that’s more red flags than a Soviet parade.

    OP, as others have said, you gotta gtf outta there ASAP. Look into resources for domestic violence; it’s a disturbingly similar situation afoot here.

    If it were me or a friend of mine in your shoes, I’d say:
    -Document everything: take screenshots, write it down, print it off (including the screenshots, emails, any digital communication), and keep a copy in 2 locations. Perhaps one copy at home, and another in a safe deposit box or at the home of a trusted friend or family member.

    -Tell everyone in your sphere what’s going on. Spouse, siblings, neighbors, friends, nanny, dogsitter, doorman at your apartment building, garbage collecter—everyone. Get your village mobilized and ready to help you.

    -If you don’t have a therapist &/or an attorney, consider it.

    -If you have stuff at your office that’s personal property that is sentimental to you, start slowly bringing it home (or, alternatively, arrange with security or another coworker who can keep their mouth shut to collect it for you & mail it to you). If El Creepo asks, you’re just switching up your décor because hey, spring cleaning! Get some cheap stuff from the Dollar Tree or that rack at Target to replace it if you really want to throw him off the scent.

    -Read “The Gift of Fear” by Gavin de Becker.

    -Consider reaching out to the HR rep who was canned. I bet dollars to donuts she’ll have insights.

    -Beef up your home, personal, and online security: always lock your doors & windows, even when you’re home/awake. Consider a Ring camera, dashcam, or other surveillance system. Be mindful of your surroundings. Tell neighbors/neighborhood watch/doorman/little old ladies on your street (better than any security system!)/whomever what’s going on so they can watch your back, too. Lock down social media, change passwords, maybe change your phone number & email (or use burners). Harden your targets.

    -Line up all the ducks starting now, so that when it’s Go Time, you can make a clean break. When the day comes, resign via letter, effective immediately. Mail back (using a burner return address) any work items you may have at home. Go no-contact. Straight-up ghost.

    Plan ahead now so that when (not if) you bounce and Boss flips a tyrannosaurus-sized turd (as these types do whenever they lose control), you’ll be ready.

    And please keep us all posted. We’re rooting for you!!

  172. Broomhilde*

    This is one of the few cases when ghosting a job is perhaps an option to consider. Either way, this is waaaayyyy too obsessive. Get out of there, OP. Don’t pass go, don’t collect 200 €, run like Hell and all of Hoboken is behind you. Don’t listen to whatever your boss says. Bloody liar, he.

  173. Amy*

    It almost sounds like he would be a terrible reference or flip on you. I’d talk to your husband for support and start looking for a new job. Once u find one – even if it’s not your dream job but just an income source – put in your two weeks. Tell him an opportunity came up to do whatever it is and you’ve always wanted to. Tell him your husband supports it and you appreciate him. If he freaks out just walk out and cut your losses. If he then is crazy just send this link to anyone that cares and tries to flip on you.

  174. Rach*

    This honestly sounds to me like your boss wants a dominant/submissive type relationship with you, where your entire life and being is focused 100% on his needs and wants and whims. In fact, it seems that he has convinced himself that such a relationship already exists between the two of you.

    Or he’s starting a cult and you are his first victim.

    Either way, you should leave that job asap. Leaving that job is more important than having another one lined up at this point. Also maybe look into marriage counselling? If your job prevented you from being fully present in your marriage, then there are probably some things that need to be restructured in your marraige, too.

    Good luck.

    1. UKDancer*

      The boss sounds like he’s watched Secretary and 50SOG and is trying to re-enact them in his workplace. Deeply creepy and encroaching. OP should get out and stay out. A good EA won’t find it difficult to get another job in most places (certainly in London they’re like gold dust from what I’ve seen). Leave this unsettling and creepy individual and be happy somewhere else.

  175. Holly*

    Echoing everyone one else, get out immediately. And please look into safety plans before that, Captain Awkward was mentioned and that may be a good place to start as she has recommended safety plans to people writing in before. But this is extremely scary and I am worried for your and your husband’s safety. Please be careful.

  176. Scredly*

    Not sure if it’s been said amongst all the comments, but I wonder if the HR Generalist was really doing the things they were accused of, or if the CEO let them go because they were taking some of the OPs attention. It would be classic isolating behavior from an abuser.

  177. TeaCoziesRUs*

    Get out get out get out get out. Don’t worry about a reference – you won’t get a good one from him. Don’t work your two weeks – either take vacation or leave now. If you must work your two weeks (by please, please don’t), do NOT go on any further travel with him or be alone with him. He is unhinged enough that I fear for your personal safety.

    Then PLEASE come back and update us soon!! I am more genuinely worried about a stranger on a blog I trust than I can express.

  178. Some Lady*

    Take a look at the book Cult-ish by Amanda Montell, which talks about language and behaviors used to control or modify people’s thinking, from real dangerous cults to interpersonal abusive relationships (which the book likens to small cults), as well as to groups that might have some cultish aspects but aren’t necessarily harmful or as harmful (like being a superfan of something). It can help identify when someone is trying to use the tactics a cultleader would use in the moment so you have some armor against getting caught up in their logic.

  179. pcake*

    This is very frightening. I would consider moving out of town as I quit; this guy sounds like stalker material. At least stay with friends, parents or someone out of town for a while.

    Anything you have from the CEO in writing (emails, texts) I’d show to a good employment attorney. If legal in your area, play him any voicemails. As much of it as possible. Then when this horrendous boss starts badmouthing you throughout the industry as a crazy person to protect himself since he knows you know him to be unstable and inappropriate, you’ll have a lawyer aware of the situation in advance to give advice and when legal action is needed.

    This CEO’s behavior is that bizarre and inappropriate.

  180. PennylaneTX*

    Long time reader and this is the first time I’ve been truly scared for OP, and desperately want a favorable update. OP, if you were my friend, I would be volunteering to wait outside in my getaway car after you resign, helping you block his number and not letting you stay at home for a good long time. Please, please, get out, and take steps to ensure your safety.

  181. MCMonkeyBean*

    Oh my goodness, literally from your very first bullet this guy is out of bounds. The CEO joining his employees on all of their smoke breaks is already crossing a line IMO. Once in a while is fine, but from the very beginning this relationship is way over the top.

    I don’t know if it is a romantic interest in you or what but this is definitely not okay and I wish you all the best in finding a new job ASAP.

  182. Higher Ed Kitten Party*

    Yes to all of the appropriately horrified comments above.

    If there is a board of directors, when you leave, please PLEASE tell them what happened.

    1. Working Hypothesis*

      I am concerned for this person’s safety whether she leaves or stays! The best she can do is to get her ducks in a row so that she can leave cleanly, cutting all ties at once, which gives him minimal opportunity to do damage… and then be prepared to bring in the law if he finds ways of stalking or threatening her anyhow.

  184. Wem*

    I would send email tendering your immediate resignation. No explanation. Cut this person off immediately.

  185. Anon for this*

    Seconding all the other comments to the effect of RUN AWAY, with the additional data point:

    Your CEO sounds a lot like my former boss, who engaged in very similar behaviour although to less of an extreme with me. Last I heard, he was being investigated for, among other things, stalking my successor.

    It sounds extreme! It IS extreme! But please be careful.

  186. All Outrage, All The Time*

    Wow. I’ve been a super high level EA for many years. None of what you are describing is normal. However, I wouldn’t be surprised if the CEO gets the boot because how does he have time to obsess over you and spend three hours in a meeting with you? I’ve never worked with an executive who has time to pee let alone carry on with all that nonsense. Is there a Board of Directors? Someone like a CFO or other C level person who has an assistant you can talk to? He is so clearly unhinged I’m sure other people must notice. How big is the organisation? If it’s small with no Board, then, yes, get out. If it’s large with a Board and other C level executives, I think it’s worth bringing it to someone’s attention.

  187. Nina Bee*

    The fact that the boss went to ‘smoke’ with them without being a smoker is all kinds of predatory fixation vibes… or grooming like Alison said.. ew

  188. Lwill124*

    I’m an EA to a CEO, and yes while this situation is obviously…creepy, for lack of a better word, I DO travel with CEO everywhere, even when I find it may not be valuable, it always ends up being valuable. I find that I have full context for meetings and action items, and it makes scheduling his meetings more tangible when I actually KNOW the parties he’s meeting with. So I’d say that’s the one part of this letter that is not odd, but my boss would never have me miss an important life event for a trip.

    1. Ermintrude*

      Your boss has a need of you for *work* purposes on trips though.
      OP’s CEO is misusing and abusing the role of Executive Assistant.

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