ask the readers: should I date my boss’s daughter?

I’m throwing this one out to readers to weigh in on. Here’s the letter:

Last summer, one of my coworkers told me that she likes me. Unfortunately I was in the process of starting a (failed) romance with another woman so I turned her down.

Well, that was half of the reason.

Flash forward to now. I’m unattached, and the aforementioned coworker is still here. We get along extremely well and I honestly don’t know if I know anyone that I have more in common with. She’s remarkably intelligent, enjoys the same academic subjects that I do, the same hobbies, etc.

The major hang-up is that she’s my boss’s daughter.

Yeah….

She knows that I was interested last year, but I haven’t told her that she’s been on my mind recently. I just don’t know what my plan is concerning our boss if she says yes. He and I get along very well, so that’s good news, but there’s this terrifying wall of social rules that I can’t imagine trying to broach, much less breach.

Should I drop it? I’ve been working here for about a half a decade and I love it more than most anything. On the other hand, I’m a recluse who hasn’t had a real girlfriend in five years. It’s not as though I feel confident in just moving on to the next opportunity because I honestly don’t know where that could possibly be.

Readers, what’s your advice?

{ 389 comments… read them below or add one }

  1. NewHerePleaseBeNice

    Should I date the boss’s daughter.

    YES! But only if you’re prepared to find another job sooner or later.

    Reply
    1. Magee

      I completely agree. I think it depends on what is more important to you- a possibility for a romance with this woman, or your job. Especially taking into consideration that you might need to leave this job regardless if the romance works out well or not. If there is zero chance of you wanting to leave this job, then I wouldn’t pursue the relationship. That’s not fair to anyone involved.

      Reply
    2. Hills to Die on

      Yes, and also be prepared to leave if it doesn’t work out. But I’m a romantic so I suppose I am weighing the opportunity for true love (rare) against a good job (not as rare, but certainly valuable). Stranger situations have worked out, so maybe this will too.

      Br careful though. 5 years is a long time to go without a relationship and you don’t want to walk into this thinking it’s something super special when it could be that lonliness and/or wanting to have someon there is clouding your perception of her. Having said that, I would probably take the risk myself in your position.

      Best of luck, and please give us an update!

      Reply
      1. Julia

        OP also says they’re a recluse, so someone who probably enjoys spending time alone. Not every single person is lonely, some are just extremely picky.
        But I agree, OP should probably figure out if there’s a chance he likes the idea of boss’ daughter better than the actual woman.

        Reply
        1. Hills to Die on

          Oh, absolutely! I totally get that being alone and being lonely and not the same thing. I’m just saying that the OP should proceed with caution initially. Emotions are funny things.

          Reply
        2. Close Bracket

          Or they are a recluse bc they have social anxiety or agoraphobia. You really can’t read anything into the word “recluse” bc reasons for not leaving the house bar all over the map.

          Reply
          1. Anonymoose

            Word. My homebody behavior is due to both social anxiety which leads to agoraphobia. That’s not to say that I don’t want love, but I would definitely want to know it’s a ‘sure thing’ before I invested any major effort (or my job).

            OP, I wouldn’t do it. More than likely one of you will leave eventually on your own. Just be good friends until one of you leave and then see if the spark is there.

            Reply
            1. Anonymoose

              Actually I am going to caveat this. If you work at a really small company in which your boss is the owner, then I might re-think it. I think I am most concerned about your relationship to your boss, as I’m sure you and her can remain professional should you not work out. However, since he ultimately controls your paycheck, those are the things I would focus on. And I would probably discuss it with him before I asked her out. Feel out the conversation, maybe simply ask him if she’s seeing anyone. If he’s a normal human being, he’ll realize what you’re doing and that you’re hedging for all parties to save face. If he’s nice, he’ll inform you what his policy is toward dating his daughter when employed with him. If he’s a total jackass, I would probably take this into consideration, but might ultimately decide that I’m not actually asking for his permission and ask her anyway. But i’m a stubborn beast, so your mileage may vary. ;)

              Reply
              1. jo

                I don’t think the OP should do anything that feeds into the idea that the boss somehow has ownership over his daughter’s love life, even if the person she might date is his employee, and even is the daughter is herself his employee. However, bringing the dad up to speed early on would be a good idea.

                I just think the daughter should be the one to do it. Anything that smells like a man asking another man for permission to date a woman … it’s icky.

                Reply
      2. Nita

        Indeed… love is not something to give up over a job. Any job. Obviously this is a potentially awkward situation, but maybe it’s worth the risk.

        And the recluse thing… maybe OP is just picky. There’s something to be said for being picky. In hindsight, I really hate that I wasn’t as picky as I should have been, and went on dates with people I didn’t feel strongly about. It never got serious, but I still managed to leave a couple broken hearts and a trail of smaller hurt feelings in my wake. I do wish I’d been more comfortable with being alone till I found the right person…

        Reply
        1. Starbuck

          Or they live in a small town with a shallow dating pool… I’m on year 4 of being single, and the combination of already having a pretty good idea of who’s around and not minding being alone means for now I’m happy to keep waiting. I have considered dating casually, like you describe, but am still weighing the pros and cons of swiping through the same half dozen Tindr profiles in a 20 mile radius… for example

          Reply
          1. TheEmployee

            Hi, I’m the OP
            No, I live in a very busy area. I just don’t like anything that resembles social scenes (parties, bars, even just walking around in the city.)

            I stay home, go to school, or go to work.

            Reply
      3. Safetykats

        Unfortunately, you may need to be prepared for changes whether the relationship works out or not. Many companies have formal policies on how closely you are allowed to work with an immediate family member. Should your boss become your father-in-law, at a minimum he would likely be prohibited from the ability to make salary decisions or conduct performance appraisals for you. A more likely outcome would be that you (or he) would need to transfer elsewhere in the company. (Most often the transfer ends up being the lower level employee, if only because there are fewer alternate seats the higher up the ladder you go.)

        I would strongly encourage you to also consult HR about the point at which you would be expected to disclose a relationship with a coworker of any kind, and with a coworker who had immediate family in management. I’ve worked in organizations who would consider there to be a clear conflict of interest until you were married, and organizations that drew the line much earlier.

        And of course, there is always the unfortunate potential for things to end with bad feelings all around, which might also make it difficult for you to stay on in your current position.

        However, there can be significant upsides in having family who have an inside understanding of your job and it’s issues. My husband and I have worked for the same company; my sister and my dad are both managers at the same company, although in different divisions. (My brother-in-law, also in management, applied for a job at that same company, but was told he would have to take a step back to be considered, as they wouldn’t consider having two management level people (even in different divisions) who were married to each other. (My company has no such policy, and there are a small number of power couples who justbwork in different divisions.) My point here is that if either you or your coworker/potential SO have ambitions for advancement, things can get more complicated yet.

        Reply
        1. Julie

          If the boss’ daughter works there already, they may not have hard-and-fast rules about conflicts of interest.

          Reply
        2. TheEmployee

          We dont have an HR dept. Were a small franchise with like 10 employees.

          Oh, this is the guy from the question.

          Reply
    3. Jen S. 2.0

      I thought I needed more information, but now I think this boils it down pretty nicely. You can do whatever you want as long as you’re prepared to deal with the consequences. You might not HAVE to find a new job, especially if you’re prepared to be a wonderful, caring significant other and not a selfish, inconsiderate jerk. But needing to change jobs probably is the most extreme possible consequence.

      If you’re prepared for that? Go right ahead.

      Reply
    4. March Madness

      Agreed.

      It depends on the value you place on your job. Is this a once-in-a-lifetime job that you couldn’t possibly land again? Does this job offer you something that few other jobs could? Could it be a career-breaker to end this job on less than stellar terms? If so, really weigh your options.

      In all other cases I say: life is short. Go for it.

      Reply
      1. Delurker/Relurker

        OP writes: “I’ve been working here for about a half a decade and I love it more than most anything.”
        That’s kind of touching, and really rare. Take care before risking that, OP, because everyone is right: You’d absolutely be risking it.

        Reply
        1. Hey Nonnie

          I agree. Really, I think you need to approach this with the mindset that you will eventually have to choose one or the other; so it will help if you can get clear in your mind which one (job or relationship) would be more important to you in the long run.

          If you’d choose the job, it may not be worth even trying / starting to date her. You’d probably just end up hurting her.

          That said, 5 years is a pretty long time to be in the same job, and maybe this is the push you need to take a look and see what else is out there.

          Also, IF you decide to date her while still at this job, I think it would be wise to have a conversation with your boss about work / life boundaries. Better to get it on the table upfront than to have misunderstandings later.

          Reply
        2. Girl friday

          I can see that it would be a problem to risk it. But, if people quit jobs because of managers not workplaces, then the corollary must be that people love jobs because of good managers; and good managers would be even nicer to have in the family. He/she can always get a better job.

          Reply
        3. TheEmployee

          Hi, it’s the OP
          Yeah, I changed my entire career path because of this job. I work with people who need help, and I have never felt so useful.

          But, then I go home.

          Reply
          1. Girl friday

            Do you have fun things in mind to do together beyond just the obvious? Maybe there’s some prep work for you to do while you’re doing the introductory dates. Because being single isn’t really boring or lonely, so don’t miss out on a good opportunity, but work on that too. Make your life so fun that she wants to date you, before you get involved with someone and it it’s too late.

            Reply
        1. Risha

          I would never in a million years have willingly worked with my ex-husband, and we never even argued about anything until the very end. I wouldn’t even play on the same Scrabble team with him after the first time or two.

          Reply
          1. AnonEMoose

            LOL! Our friends won’t let my husband and I play Trivial Pursuit as a team anymore. It worked fine for us…and we both suck at the sports questions, but…y’know…

            Reply
          2. Scrooge McDunk

            I’ve been with my partner for nearly nine years and just discovered last week that I cannot, under any circumstances, play Pictionary with him.

            Reply
        2. Michael A Packer

          My wife and I have worked in the same office for 20 years at this job… you have to learn how to do it… we are now both manager level.

          Reply
        3. Triple Anon

          Yeah. LW should choose between the job and dating the co-worker. Regardless of how it goes, working together could cause problems.

          Reply
    1. JokeyJules

      +1

      As the wise Tony Soprano once said, “Don’t shit where you eat”

      Don’t date your bosses daughter. He can stop being your boss, but she can’t stop being his daughter.

      Reply
    2. LBK

      I think he needs to pre-emptively leave the job before they date. Don’t put the office through that mess.

      Reply
      1. KellyAF

        I don’t agree, but I do think he needs to decide first which he values more: the potential romance, or the job. Best case scenario is both go wonderfully and there’s no need to choose, but worst case is that he would need to pick one (which could be a result of either the job or the romance going bad). Best to get that clear in your mind first, think through potential consequences, and then weigh the costs and benefits with your values in mind.

        Reply
        1. LBK

          I mean, I don’t think he needs to quit before he even asks her out. But if they do end up going out on a few dates and find that they click, I think he needs to be prepared to quit pretty soon after so they aren’t working together while in a relationship. The issue with waiting until you break up to stop working together is that it puts the rest of the department through hell in the meantime. I think it’s kinda selfish to do that.

          Reply
          1. LBK

            (Also, better to work through the job situation while you’re still on good terms – consider the letter where the couple agreed that one partner would quit if they broke up but then when it actually happened she refused to leave.)

            Reply
          2. Starbuck

            This sounds nice, but do you really expect that anyone would follow that advice? Have you, would you? Sacrifice their job to save their coworkers potential drama? Seems like a stretch.

            Reply
            1. LBK

              Would I want to spare my coworkers from a potential messy public breakup that would probably forever tarnish my reputation with them? Yes, absolutely.

              Reply
      2. Specialk9

        I don’t know, I think OP should walk very very carefully, but she could make it work.

        My best recommendation is that she and Boss-Daughter have a really thorough discussion about how to navigate a potential breakup, since it’s by far the most likely option. Make a deal on breakup (eg neither will ghost or breakup by text, phone is ok, be kind, “it’s not working out” is enough reason and no badgering for whyyyyy) and how to behave post-breakup.

        I made a deal like this when my two BFFs dated in college, with lots about the limitations of what they could tell me about the other or about conflict, and that I refused to pick sides when they broke up. It actually worked well — both because they generally followed it, and because it helped me get clear in my mind what I was ok with and where my boundaries were. (Though man that breakup was HARD to live through! Though interestingly she was invited to his wedding, years later, and we had a good time celebrating together.)

        Reply
        1. Roja

          This was my thought too. Give it a go, but before you talk about literally anything else, discuss how you’ll handle interpersonal office relationships both in the case that things work out and in the case that they don’t. If they’re both reasonable people and communicate, things could work out. If they’re not, then it’s more like to be a train wreck. There are many people who can and do work with S/Os or ex-S/Os and it’s not a big deal; plenty of others who… um, can’t, to put it nicely.

          Reply
          1. myswtghst

            Agreed. And if OP doesn’t feel like they can have this convo with the boss’s daughter, it might be a sign that it’s better if they don’t date, because they’ll need to be able to communicate openly and effectively about this stuff from the jump if they don’t want it to end in a mess.

            Reply
    3. AnotherAlison

      Yeah. . .In this particular scenario, that’s where I land, too.

      I actually met my husband at a job, and my mom worked there. She was not his boss, and didn’t work in the same area. We were pre-college graduation when we met, and this was not a job either of us loved or wanted to keep long term, and were just dating for fun (whereas the OP sounds like he is purposefully looking for a serious relationship).

      I didn’t work there very long, but he worked there for a few more years, and it was weird for him to work with my mom. They got along, but gossipy coworkers would tell my mom things that I already knew that were not her business.

      Ugh, I just don’t like the mix here. There are a lot of opportunities for this to change the situation at a job the OP really likes. I don’t think I would jeopardize that. I might become really good friends with the boss’s daughter, and maybe at some point, dating would be unavoidable, but maybe by then, someone in this discussion would work somewhere else.

      Reply
    4. Rachel01!

      I do not think you should do it. The person you know at work, is the work face. What they are like in their private lives in a different matter. I’ll share my experience with you. You need to decide how you’ll handle it if the private individual is not what you imaged, and what the fall out might be.

      I worked in higher ed. There is an adjunct that I’ve been interested in a long time, that I worked with for 4 years. This past year he didn’t work for the university and he made it clear that he wasn’t planning to coming back. We’ve had a casual acquaintance where we would talk about our private lives, brief notes to each other on Facebook for a few years. I always thought he was involved, but that had ended a couple of years ago. He was pleasant, high energy, had a great sense of humor, but a bet scattered.

      Well I found out that he doesn’t bathe, we had a date to stay over, he hadn’t bathed for 2 days, stunk to high heavens. His home is filthy, turned out his exwifes main complaint was that he was lazy. So true, his home was nasty and dirty. He was taken to court for back child support for the last two years. He had sold him home and was living off the income. He would be bouncing off the wall for a few days, extremely hyper than turn around a be total down, dragging his feet. Doesn’t believe in medication and tried to talk me out of taking antipressants. When I told him tha I expected him to shower before our date he said that ne believed in natural scent, went into this long comment about my nose being sensensitive and that I was demanding.

      Had a conversation a few days later and he told me that I was the wrong calibre of person. Now because of the child support suit, he wants to come back to campus. I really liked this man, but what I learned has changed my liking this funny man, to thinking he’s blooming crazy.

      After thinking about what I’ve shared and a few others have …. are you willing to take this route & find out that you truly do not like this person once you get to know them and see them every day in the office if it blows up. She could have some habits that are a total turn off.

      Reply
      1. I Wrote This in the Bathroom

        Yes this exactly!! is my thinking, and the reason why I am eyeing skeptically all the comments on here advising OP to take a risk in the name of love. Romantic 19-century kind of LOVE! <3!! is a wonderful thing in theory, but what about when you move in with the person and find out that they firmly believe in "if it's yellow, let it mellow", and you don't? (something an ex did that I tried to force myself to live with). Or that they can only fall asleep if Family Guy is on TV with the volume turned all the way up? (something another ex did, that I could live with, but others might not.) If your idea of a perfect weekend is going out, doing things, and meeting new people, and theirs is never leaving the house? if your financial habits are the opposite of each other? You already know you get along very well when things are good, but do you know what this person is like when you have a conflict? do they fight fair, or will they go "into this long comment about my nose being sensensitive and that I was demanding"? You will not know most of these things until after you've spent a lot of time in a close relationship with this person. It is a gamble. And in OP's case, there's a hell of a lot to lose.

        I am not even reading it in OP's letter that it's LOVE!!SHIFT1! on either side. OP is sort of interested. Boss's daughter was sort of interested a while ago.

        Reply
        1. Nita

          Believe me, I can relate to a lot of the above! Totally been there, even over really big things. If it’s love, it’s love, and you just have to learn to tolerate the things you don’t like about the other person if the relationship overall is worth it. And of course it means being in for some really difficult times because you have the same goal in mind, but one of you wants to climb a mountain to get there, and the other one wants to tunnel through it, and there’s absolutely no way to do both. I do think not fighting fair is a deal breaker, but putting up with all that other stuff may just be a necessary evil :)

          But of course only OP knows if their feelings are worth putting a much-loved job on the line. For all I know, they may not be.

          Reply
          1. staceyizme

            It can take a long time to sort out a process of how to have difficult conversations. I have to admit that I no longer care for the expression “fight fair” because it’s adversarial and also because things are seldom truly fair in relationships. Finding a way forward through difficulties is a set of skills that takes a long time to build. I don’t know what the Final Answer on conflict management is, but as I’ve gotten older fighting is less of a go-to for me, fair or otherwise.

            Reply
    5. GlitsyGus

      Honestly, you may need to leave if it goes well. It could very well reach a point where separating your “Daughter’s Boyfriend” and “Good Employee” roles with your boss will just get too messy. It will depend on a lot of factors, it may go swimmingly, or you may find your boss being more critical because now you are “taking care of his little girl” or whatever.

      Basically, for better or for worse, realize you could have to quit if you choose to date her, if it still seems like you like her enough to take the chance, go for it.

      Reply
    6. HistGradStudent

      I must say, it’s amusing that Det. Santiago is giving this advice ;)

      But I agree that OP must consider the pros and cons. What is more valuable, your job or the chance at this romance? And, as many others have noted, the success of the romance does not guarantee your position with this company.

      Reply
  2. MuseumChick

    If you have no plans to leave your job very, very, very soon, do not date your boss’s daughter.

    Reply
  3. seller of teapots

    Life is short. Listen to your heart and reading your letter, it sounds like your heart wants to give it a shot.

    Good luck!!! Keep us posted.

    Reply
  4. Rae

    I started dating a colleague three years ago, and we’re still together now.

    My advice is to make a list of the pros and cons and work out what’s a deal-breaker and what you can accept.

    Best case scenario? You get together and live happily ever after.
    Worst case scenario? No girlfriend, no job.

    Don’t deny yourself an opportunity to be happy, but ask yourself the relevant questions:
    1) If you date and it doesn’t work out, would you still be able to work with her?
    2) If you date and it does work out, if it became necessary would you be willing to leave your job?
    3) If you don’t ask her out, will you regret it?

    I wouldn’t ask your boss for his views. I’m not a fan of asking the parents of grown adults for their views on dating their children.

    Good luck!

    Reply
    1. grace

      Yeah, please don’t talk to your boss about this! You’re an adult, she’s an adult – make an adult, informed decision. If it doesn’t work out carry on professionally; if it does, it’ll eventually come up and the two of you can decide how you want to tell her dad.

      Reply
      1. A tester, not a developer

        I’m truly hoping they are both adults – not “I’m a 45 year old recluse, and she’s working for her dad’s company fresh out of high school. It’s true love!”

        Reply
    2. Not a Real Giraffe

      I wouldn’t ask your boss for his views. I’m not a fan of asking the parents of grown adults for their views on dating their children.

      +1 to this. If you do start dating this woman, I would then disclose it to your boss and have an open but professional conversation about how to mitigate any impact this new relationship would have on your work and your relationship with your boss. But I would do it after it becomes a reality, not before.

      (At a minimum, you don’t want to tell your boss you intend to pursue his daughter, not have it work out the way you want, and then always have your boss thinking of you with your romantic intentions for his child in the back of his mind.)

      Reply
      1. Rachel01!

        If he does decide to date her. Do not sleep with her right off the bat. It’s easier to walk away & maintain a friendship if sex isn’t involved. You need to see each other’s homes & see how they live.

        People can keep their apartments clean, etc. for dates for the first few months. At the third month is when the true self pops through in bits and pieces.

        Reply
    3. LBK

      I mean, from the perspective of asking her father for “permissions” or whatever, he shouldn’t talk to the boss. But as one employee planning to date another employee it’s probably advisable to bring it up.

      Reply
      1. Julia

        Maybe, but imagine asking your boss for advice/permission to date another employee, and then later the boss finds out you were asking about their daughter. That can’t leave a good impression.

        Reply
        1. LBK

          Do you think it’s going to leave a better impression for him to find out later, possibly through the grapevine? I mean, I don’t think the OP needs to ask the boss before he even finds out if the coworker/daughter is interested, but if they go on a date or two and they click, I think they need to be upfront about it ASAP.

          Reply
          1. Julia

            That’s not what I said. I just said that if he were to ask the boss for permission to date a co-worker, he should definitely mention that the co-worker in question is the daughter.
            Whether he should ask or not, I’m not sure – I feel like he should ask the woman out first before discussing it with her father.

            Reply
            1. LBK

              Oh, I wasn’t suggesting that the OP just tell the boss he’s planning to date a coworker but not specify which one! I was responding to this:

              I’m not a fan of asking the parents of grown adults for their views on dating their children.

              I feel like this just completely ignores the part where the parent in this case is also the OP’s manager. People were framing it purely through the “asking a woman’s parent if it’s okay to date her” lens when there’s a very important other consideration to be made here, whether the coworker were the OP’s boss’ daughter or not.

              Reply
      2. Dianne

        I think he needs to ask permission but in a less formal way. Maybe in a group setting the group goes out and the dad can see the daughter gets on well with OP. If the daughter is living with the dad then she will likely bring up she’s dating OP. But this is when OP needs to be prepare for a fallout – boss may not like him,not like the scenario in general of co-workers dating, maybe wants the daughter not to be dating (yes even middle aged women have terribly protective dads). I would say to OP to go for it, if you can now see potential for a long-term relationship. It’ll reflect badly if you break the relationship. It may be unfair and not ‘by the law, but when you bring emotion and heartbreak into the office and the big boss is the dad, you will be out of there pretty quick he won’t get rid off his daughter. Everything will change and you may end up paying the price of your job. Good luck.

        Reply
    4. Kalros, the mother of all thresher maws

      Best answer. Nobody can tell you “yes, great idea” or “no, terrible idea” and promise you that you made the right choice. “Don’t shit where you eat” is good advice; “seize the day, true love is worth taking a chance” is also good advice. You’re the only one who can decide whether the risk is worth it. And that’s scary, because what if things go wrong? And they could go wrong, in many, many ways. But they could go very right, too, and it might be worth it to you to try. But only you can decide that.

      Don’t bank on being able to balance dating your boss’s daughter with keeping your job and your uncomplicated relationship with your boss; stranger things have happened, but it’s not terribly likely. So weigh what matters more to you: your job, or your crush. Do you have a heart-racing crush, or is it more of a mild interest that feels stronger because she’s a viable prospect? If it’s the latter, there are other women out there. But if it’s the former, there are other jobs out there, too. Ask yourself what you value and what you’re willing to sacrifice, and make your decisions accordingly.

      Good luck!

      Reply
      1. TheEmployee

        “There are more women out there”
        Well, like I said in my letter, that really doesnt seem to be the case. I am… Very bizarre. Thus, I don’t attract people very much.

        I’ve thought about it for the better part of a year: we seem extremely compatible. She can’t open her mouth without saying something I find fascinating.

        Moreover, I don’t tend to like people. This is something of a rarity.

        Finally… My job is incredibly special to me. It’s really why I wake up in the morning.

        Reply
        1. Sammy

          This is a good start to getting to know someone. You can be friends with a very smart woman without having a romantic link but it may naturally develop. But if just seeing her at the job makes the day easier and what she says is fascinating, it still may not be enough to to risk your job.

          Reply
    5. Risha

      This is excellent advice, but once he decides what he wants, he still needs to actually talk to her before making any final decisions. He doesn’t even know if she’s still interested! A year’s a long time.

      Reply
      1. Kalros, the mother of all thresher maws

        My read of the letter is that he’s trying to decide whether asking her out is a good idea, so if he decides to go for it, talking to her is a given (he’s not sure how to handle “if she says yes”). If he decides to drop it, that’s that.

        Reply
    6. Geek

      Good idea listing the pros and cons.

      Unless you have a contract, you don’t have a job guarantee. Be careful sacrificing personal gains for work.

      Chances are good that your relationship won’t work out. Most don’t. That’s why I was really reluctant to start dating my best friend. I didn’t want to end up without my best friend. Twenty-two years and 4 kids later, I’m glad we did. :)

      Is the absolute worst case that you need to find a new job after being there 5 years? That’s not really a horrible thing.

      Reply
      1. The Librarian (not the type from TNT)

        “Is the absolute worst case that you need to find a new job after being there 5 years? That’s not really a horrible thing” … unless you work in a field like mine where the job market is regional instead of local, or otherwise extremely competitive, and finding a new job on short notice is just not feasible. And this is the kind of situation where the OP is definitely going to need to have a Plan B.

        I once dated a coworker, and working with her after things didn’t work out after a few dates (it wasn’t really even a full blown relationship) was extremely awkward for both of us. And this was without the wrinkle of the coworker being related to the boss. I was fortunate that I was on my way out of the company and had a new job within a couple of months.

        That being said, if you really have strong feelings for this person OP… sometimes in life you just have to take a gamble. I’m just not sure I’d take this gamble myself without any sort of feasible escape route in place.

        Reply
    7. Armchair Analyst

      I see this like one of those consulting 2×2 squares. Girlfriend Y/N Job Y/N
      So YY would win. And NN would lose. Are YN or NY really possible? Desirable? Hmm….

      I think the LW should at least broach the subject with the boss’s daughter and see if she’s interested. Then… see what happens! And let us know!! We’re all cheering for you!

      Reply
  5. Normally a Lurker

    Woft. I’m gonna go with no. Unless you plan on finding another job on the sooner side of sooner or later.

    That is just a recipe for all kinds of office political trouble in ways that I know I certainly wouldn’t want to deal with.

    Reply
    1. Normally a Lurker

      Sorry, to expand.

      If things go well – then you manager is you gf’s father. Which puts him in a position of managing someone that is personally related to him.

      If things go badly – then your manager is your ex gf’s fathers. Which puts him in a position of managing someone who *was* personally related to him.

      Either way, there is very little that isn’t going to look like some kind of favoritism or retaliation – even if it’s not – bc of the relationships of the ppl involved.

      Reply
      1. Amber T

        Agreed! But also – Boss is managing his own daughter, so there’s already political weirdness, because you should be managing your own kid (or anyone you’re related to).

        Reply
        1. Alcott

          Well, we don’t actually know that. We know boss and daughter work for the same company, but could be in different departments with no overlapping management.

          Reply
        2. SoSo

          Not necessarily. The LW never stated that the Boss was managing his daughter or that they were on the same team/same group under the Boss, just that they are co-workers. The daughter/co-worker could easily be in a different group, team, or even department. I still think step one should be that LW check the company policy on romantic relations in the workplace, because it may not even be an option if they both want to keep their jobs.

          Reply
        3. Amber T

          Nevermind – above comments are right. I read it as OP and coworker are on the same team but I see that’s not necessarily the case. My bad!

          Reply
  6. Clorinda

    There are other women. There are also other jobs. Which one matters more to you? Because there are just too many things that can go wrong trying to combine THIS job with a relationship with THIS woman.
    PS: That doesn’t mean you should quit before asking her out. It does mean you should have a plan to transition out of this workplace if you date and things go terribly wrong.

    Reply
    1. Jen S. 2.0

      Not for nothing, LW might have to transition out of the job should things go terribly right, as well. It is awkward for the boss to manage his daughter’s long-term significant other, or, eventually, daughter / son-in-law (I’m not sure we definitively know the gender of the letter writer).

      Reply
    2. Kalros, the mother of all thresher maws

      +1. Even if you’re sure you can remain professional no matter how things turn out, dynamics will shift in ways that aren’t always going to be within your control. If that’s understood, decide what matters most to you, and go with that.

      Reply
    3. Jesmlet

      Perfectly said. I don’t think this should be a hard no. Are you more willing to lose your potential future with this company for your potential future with this woman?

      Reply
    4. Mad Baggins

      This!! OP as you weigh the pros and cons, this is actually the most important part of your mindset: you WILL be able to find other women you are interested in, and you WILL be able to find another job. If you approach either of these out of desperation you’re not going to make an accurate or happy choice!

      Reply
  7. Red Reader

    Jesus wept. Don’t date your coworkers, the boss’s daughter, OR YOUR COWORKER WHO HAPPENS TO BE THE BOSS’S DAUGHTER. I mean, this is the part where everyone who’s married to their boss’s daughter comes out of the woodwork to tell you it’ll be fine, but really, this is a terrible idea.

    Reply
    1. AvonLady Barksdale

      I’m less concerned about who her father is than that she’s OP’s coworker. Add her dad and it’s just a recipe for disaster. Don’t do it! Or, if you decide to do it (the heart wants what it wants, dontcha know), start job-hunting before the first date.

      Reply
      1. Samiratou

        Funny, I’m kind of the opposite, depending on how close a coworker we’re talking about. If you’re not on the same team or don’t otherwise work closely together, dating coworkers can be fine, particularly in larger companies. If the coworker was the daughter of a boss on another team that is not related to yours, also not a big deal. But that she’s the daughter of the LW’s boss? No. That’s just going into places that are going to get awkward, no matter what.

        Reply
    2. Tell me more...

      Eh. I know many, many happy couples who met and started dating as coworkers. Myself included. I vote to take a chance on it and trust that they can all be mature about if things don’t work out.

      Reply
      1. Antilles

        The difference here is the fact he’s the boss’ daughter. No matter how mature OP and the daughter are, if it doesn’t work out, that element of “…that’s MY kid” that will never go away.

        Reply
      2. LBK

        I think this depends on so much, like how closely you actually work together, how long you continue to stay working together after you start dating, how good you are at setting up boundaries at work, your mix of personalities, etc. I love my boyfriend very much but we’re both strong introverts and I think we would kill each other if we lived together AND worked together and basically saw each other 24/7. As it is we both like to have a little alone time to decompress after work, and when we both work from home we pretty much stick to our respective rooms.

        Reply
    3. Zennish

      This. Even if it works out as a relationship, at best your boss is suddenly far too involved in your personal life, whether they want to be or not. At worst, every relationship issue suddenly becomes a career issue after boss’s daughter vents to boss.

      Reply
      1. Specialk9

        I mean, not just on TV these days, not to get too political! Sexually transmitted power, sigh.

        Reply
    4. pleaset

      I just want to point out, regarding dating coworkers: it might be risky, but it is also very common. People spend lots of time at work, and many many people have dated coworkers. I think calling it a terrible idea is not accurate: probably work is a place here a significant portion of people have met future spouses.

      Risky yes. Possibly terrible yes. But also possibly great.

      Reply
      1. Red Reader

        Conveniently, as I am already married (to someone I don’t work with), my personal opinion that dating one’s coworkers is a universally terrible idea doesn’t actually have to matter to anyone.

        Reply
  8. Amber Rose

    If you’re pretty sure your life won’t be completely destroyed if things go sideways, I say go for it. Life’s too short to worry about stuff like “my boss’s daughter.” You can’t marry your job, or cuddle it at night. I’ve worked with plenty of happy couples.

    Reply
    1. grace

      This is where I am, too. :) Just make sure you know what you’d do if it DOESN’T work out.

      And I didn’t see anything in the letter about it, so … make sure she’s still interested, too, before making any hard and fast decisions.

      Reply
    2. Star Nursery

      I don’t think it is a definite yes or no since you aren’t direct reports or one of you is not the supervisor of the other. It could be a great relationship and it could also go sour and make work awkward.

      There are multiple married couples working at my employer (800+ employees size). I can count four couples that I know of who are married and work here. I think at least one of them met here. They pretty much work in different departments and I haven’t heard of any issues in my company. However at another job there were nepotism issues that I had heard of… There were working at that company… Variety of relationships… Parents and son/daughter, A husband and wife, aunt and nephew and biggest was a boss and his girlfriend but it was a smaller family owned company not as many departments and yeah.

      Reply
  9. Wannabe Disney Princess

    Is there anyway you can try to spend time together outside work without it being a date? Like a happy hour, or something? Just because you have a crush on her AT work doesn’t mean it will translate well outside the office walls. There are coworkers that I get along with EXTREMELY well. But when we’ve done group outings, I’ve discovered that I wouldn’t want to be close friends with them. (And I’ve discovered the reverse was well, people I want to club with a golf club as coworkers I genuinely enjoy as people.)

    Reply
    1. Myrin

      That’s what immediately came to my mind as well. From the letter, it seemed to me like OP only knows this woman through her work environment, and before deciding on going for a relationship that’s almost certain to drastically change your life in some ways, your should definitely try to find out if you even get along with her at all when divorced from a work context.

      Reply
    2. A Person

      Agree, since you share common hobbies there’s nothing wrong with developing a friendship. With her, or anyone else who shares your hobbies for that matter.

      Just be aware if you start dating her specifically you will probably need to look for another job, whether it works out or not. And you might blow your reference to crap if boss/dad is not happy about the relationship.

      Too many complications in my opinion.

      Reply
    3. Environmental Compliance

      +100

      There is a very, very short list of people that I both greatly enjoy working with and enjoy spending significant time outside of work with. Working Professional EC is also a very different person than At Home, Refusing to Wear Pants EC.

      Reply
    4. LBK

      This is such a good point. There are a lot of coworkers I enjoy at work and whom I even enjoy at happy hour after work but that I’d never go out of my way to set up social time with if it weren’t somehow connected to our mutual employer.

      Reply
    5. Emily S.

      This is a very good point. I think it’s unwise to date her, LW/OP, but that doesn’t mean you can’t be “work friends” — provided you do not become more than that. If that’s impossible without your romantic feelings getting in the way, then don’t. Just don’t.

      Reply
    6. sunshyne84

      That’s exactly what I thought. It can be weird once you change from work friends to outside of work friends. I would just try hanging out slowly to get a feel on the situation. Five years is a long time and she might be over that whole idea by now.

      Reply
    7. JessicaTate

      +1 to this. See if you can start by becoming better friends with her in non-work settings. It will buy you some time to think things through. If you find that the sparks keep flying and growing outside of work, maybe you’ll determine it’s worth the risk — and, to be clear, the risk is that this job will become a very unpleasant environment and not something you love anymore. (And, at that point, you’ll both have a little investment and trust and could talk about the “what if” scenarios together. She has a stake in this too!) But you may also find that the sparks don’t really fly, or that she’s nice and great, but maybe not quite as good a fit for you as you thought. And then the whole thing is blissfully moot.

      And to your concern about not being sure when the next opportunity will come along… I completely understand feeling that way. But, I’m here from your future to tell you, definitively, that feeling like you just don’t have other options is never a good reason to get in a relationship. Never. It creates a bad dynamic. So, just cross that out of the “pro” column for “Date this Girl.” (There are other pros, but this shouldn’t be one of them.) It may take time and discomfort in the dating scene, but you will find your person with time. And it’s worth that time and effort. I’d rather be single for five years than have been in a “real relationship” with someone who’s just a bad fit, and I wish the same for you.

      Good luck, whatever you decide.

      Reply
  10. Manders

    This woman’s your coworker and her dad’s your boss, so–does she report to him? Is this a family business owned by the dad? Is the daughter planning to work at this business with her dad forever?

    If it’s a family business, be aware that those can be really high drama if you become a member of the family. This job sounds very important to you. I’m not saying you absolutely can’t go for it, but if you do, make sure you’ve got some cash saved up and an exit plan if you need to leave.

    Reply
    1. TheEmployee

      It’s a franchise. We have about 10 employees in this branch. He’s there almost every day, as am I. She’s there maybe 2 or 3 days a week.

      Reply
  11. Nonsensical

    Don’t date someone because you don’t think you’ll never find another opportunity. That is a bad foundation to base a relationship upon.

    Reply
    1. Um, What?

      That was my exact reaction. I was a little put off by the “I’m not sure when I’ll have another opportunity.” That’s a piss-poor reason to date someone, honestly. You’re either attracted to them and invested in pursuing them or you’re not. There are definitely good reasons to consider whether that attraction should be acted on, but don’t don’t don’t let that reason be that you may never have another opportunity.

      Reply
      1. Kalros, the mother of all thresher maws

        Oh! I read that part too fast and thought it meant another job opportunity. I fully agree with this – “this is my last chance to not die alone” is so very rarely true, and shared hobbies and interests don’t always translate to romantic compatibility, either.

        Reply
      2. Lou

        Exactly. And OP turned her down the first time to pursue someone else. I can’t help but think that it’s the relationship they’re looking for, not the specific person.

        Reply
      3. Salamander

        +100. There’s an air of settling for what’s in front of one about this situation, especially since the OP turned her down previously.

        Reply
      4. MicroManagered

        I kinda hope it was a poorly-worded way of saying “I don’t know when/if this kind of attraction will happen again.”

        Reply
      5. Nita

        I’m reading that as another job opportunity – OP does talk about how much he loves his job, and may be thinking through the possibility that if he pursues this girl, he will have to give the job up.

        Reply
    2. Mayati

      Agreed. OP, dating someone because you think they’re your only option for the foreseeable future is unfair to both people. That mentality would keep you in a potentially bad relationship out of the fear that “this is as good as I can get,” and it would treat her like a person to fill the girlfriend slot in your life instead of like the individual she is. I’m not saying that’s your only reason for wanting to date her, but you absolutely need to get rid of the whole scarcity-mentality part of your reasoning.

      I’m a recluse too, I get it. I barely dated at all before I met my fiance. One of the people I dated was the Wrong Person, but I liked a lot of things about her, and that plus the “what if I never meet another girl who ticks X, Y, and Z boxes?” desperation felt like enough to get into a relationship. It wasn’t great. The solution to my trouble getting out and meeting people was to work on myself until I was ready to get out and meet people in a low-stakes, “if this person doesn’t work out, some guy or girl will come along who’s a better match” sort of way. You dating this particular girl is VERY HIGH STAKES, though, and that’s not a great way to start a relationship. Sure, things might work out, but if they don’t, there would be impacts on your career *and,* it looks like, your emotional health. (“I’m a recluse without many good options, so I’m eager for this one opportunity” is not an indication of emotional health, even if you are, in fact, a recluse without many good options…I know because I’ve been there! But I could be wrong about your headspace, so take this with a grain of salt.)

      So in addition to considering what kind of a relationship you have with your boss, what sort of professional boundaries are present in your workplace culture, what your other career options are, etc., consider what sort of impact a messy breakup would have on your emotional health if it meant you also had to leave your job (or, at least, feel less comfortable and at home in your workplace). And consider whether you would date this particular person if you knew you had other options right now.

      Reply
      1. LDP

        Coming from the opposite end of this, I was the girlfriend of someone who kind of looked at me like I was as good as it was going to get for him. Even if you think you’re not letting on that that’s how you feel, it will come up. And I had to spend a very long time re-building my self-confidence once I realized I needed to get out of that relationship. I’m hoping that this isn’t how the OP really feels about their potential partner, and it may have just been a phrasing issue. But I agree with the other advice throughout this thread of getting back out into the dating world in even the smallest capacity first, even just for your own well-being. If you feel like you do have other options in terms of relationships it will either reinforce that you really do care about this woman, or maybe you’ll realize she lacks other qualities that you would want in a partner. Either way, you’ll be able to make a dating decision from a position of strength, rather than feeling stuck.

        Reply
      2. TheEmployee

        Last year I turned her down mostly because she was my boss’s daughter. People are getting WAY too much tunnel vision on the part where I mention how lonely I am.

        1) I mentioned that specifically to avoid getting a flippant response of “there’s other fish in the sea”. It’s useful context to know that if I turn her down, I expect to be alone for at least another year or longer.

        2) how is the feelinf of crushing loneliness not a factor here? It’s all well and good when you’re not suffering through it, but I am. And it’s not like I’m interested in some substandard person, she’s really excellent. She’s prime partner material as far as I can tell. She’s just a damn Capulet.

        Reply
    3. annakarina1

      Yeah, this shouldn’t feel like a now or never thing, it puts way too much pressure and put the person they are pursuing on a pedestal. I can’t tell how old the LW is. If he is over thirty, I could see how he could feel like he needs to settle down to keep up with a lot of other long-term couples, but it still isn’t right.

      I myself have been single for five years, but still wouldn’t treat a crush or potential interest as someone to jump on as a last-ditch effort, that’s really unfair to the other person.

      Reply
    4. Excel Slayer

      This is how I feel.
      This is a romantic opportunity that means a lot of risk and that you’ll probably have to move jobs. OP, you should only pursue this if this women is worth more to you than the risk and the stigma that will come out of it (not all your coworkers are going to be fans of this, and it will come out).

      Reply
      1. Salamander

        Yeah. She really didn’t turn the OP’s head before now. I might feel differently if she had, but there’s a lot of risk here.

        Reply
        1. TheEmployee

          Yes she did. We talked about this again in December. So I’ve really been thinking about her as my primary love interest for 6 months now.

          Reply
    5. I Wrote This in the Bathroom

      100% yes to this. Putting myself in the OP’s position, I can confidently say that being single is infinitely better than being stuck in a bad relationship or marriage; and that’s without the work situation and the dad/boss situation thrown into the mix. Putting myself in the woman’s position, I would be beyond upset to find out that the main reason my SO had decided to date me was that he thought he’d never get another chance with anyone, and I seemed to be willing.

      To my second point, I once briefly dated a former work friend. Things were not working for us as a couple for a lot of reasons, so I ended it, but we tried to stay friends. Then a few days after the breakup, he decided to tell me that, when he’d started flirting with me and saw me reciprocate, he’d told himself that this was his “only chance to bang a hot chick”. I cannot begin to explain how awful it made me feel to be told that by an old friend. I could not bring myself to talk to him for a good part of the year. We almost lost each other’s friendship. We eventually reconnected, but it’s been just a tad bit awkward ever since. Nobody wants to be anyone’s last chance, no one.

      Reply
      1. TheEmployee

        People really are missing the focus here.
        The only reason I have not tried to date her is because she’s my boss’s daughter. She’s wonderful, as I tried to emphasize. So to say the “only reason” I’m interested is because I’m lonely is to be wildly unfair to my position.

        Reply
    6. HMM

      I agree in theory, but it also doesn’t have to be one or the other – you can both like someone a lot and also understand the probability that you might not find another person that you like that much in the near future. It’s just one factor to consider in the pro/con list. Some people call this settling but it’s not – it’s the reality of circumstances. You live in this particular place at this particular time, and unless you’re willing to make changes to your circumstances (i.e. becoming less of a recluse, moving to a more populous city, leaving this particular job, etc.) you work with what you got.

      But then again, I personally subscribe to the idea that love is all about choices, not necessarily fate or destiny.

      Reply
      1. ArtsNerd

        Right. I rarely feel a strong romantic connection with people, so when I do, it’s a difficult choice to step away from that possibility. It’s not about being lonely or desperate for that one person but whether it’s worthexploring a chemistry I very rarely experience.

        Reply
      2. Zillah

        I agree with this, and I think it’s especially true if you’re not someone outgoing who regularly makes easy connections with others.

        Reply
      3. TheEmployee

        I can’t really “choose” to be less of a recluse. I hate being in places like bars and parties. I just sit outside or walk around the block.

        I live in a highly populated area.

        And I love my job more than I’ve ever loved anything.

        Reply
  12. Tell me more...

    Unpopular opinion, but I vote “go for it”. I’m in a place in my life where love and family are far more important that job satisfaction, and I’m going to assume that based on your letter, you all sound decently mature and could work through a breakup if it happened down the road. Had you mentioned any drama with boss, I might have advised more caution, but in this case I’m just going to say YES. Take a chance on love.

    Reply
    1. GRA

      I am on team “take a chance and go for it”, too! This doesn’t seem to be a whim for the OP, it sounds like they have thought things out. I say, go on a few dates and see where it goes.

      Reply
    2. Bea

      I loved working with my SO. We didn’t meet at work but we worked together due to circumstances. It actually uncovered some BS that ended in both of us leaving and strengthened our bond.

      I’ve known only family businesses and so I’m skewed. So yeah. I’m def in the “do it” camp.

      Reply
    3. LBK

      I think you can “take a chance on love” while still being pragmatic about the potential consequences to your career (and the livelihood you rely on that career for). That’s part of being an adult in a mature relationship. Life isn’t a TV show – don’t purposely set yourself up for a dramatic situation dreaming of the big payoff when it all works out and you live happily ever after together.

      Reply
  13. boo bot

    Talk to her! She’s the one who originally broached the subject, so you’re not springing it on her totally out of the blue, and she is likely to have some perspective on how her father will react. And, if she’s a reasonable human (two of my favorite qualities in a partner) she will understand why this is something you’re concerned about.

    Who knows, maybe he’s been planning the wedding since the last time she asked you out! (In which case, you may have difficulties of a different sort!)

    Reply
    1. LSP

      Yes! If she’s a reasonable adult woman, she’ll have an understanding of what dating a colleague who reports to her father will mean, and will have some insight into how her father will behave himself.

      Reply
    2. ArtsNerd

      THANK YOU. It’s not “yes or no.” She is a human adult, and she’ll have thoughts on this too. If she blows off your concerns, then proceed with extreme caution, if at all.

      If she shares them, then you have a line of communication open about how to weight the risks and rewards of this possibility.

      Reply
      1. ArtsNerd

        Given more thought, I’m switching my loyalties to team “Expand Dating Pool” if the employee has any kind of trouble navigating conflict or awkwardness, which is true for more people than not.

        Reply
    3. Thany

      +1

      Talking to her might help you decide if it’s worth it or not.

      Also, it’s possible she may not be available anymore. But you won’t know that unless you talk with her.

      Reply
  14. Leave it to Beaver

    I have a couple of thoughts.

    One – if you want to date her, find a new job. It alter your relationship with your boss and by association your job, regardless of how things go. It could be an immensely secure and loving relationship, but one day she or you will forget to put the milk back in the refrigerator and your boss will find out about it. (OR INSERT YOUR OWN METAPHOR HERE) No one needs that kind pressure.

    Two: You mention you’re somewhat reclusive and haven’t had a relationship in 5 years. Is it possible you’re fixating on this particular girl because she placed herself in front of you? (That’s not to discount her awesomeness, but there are lots of awesome people out there). Before you decide to take a step down this highly pressured road of domestic and professional bliss… go out on a few dates, ask friends to set you up, use OK Cupid, whatever. Dip your toe in the water first before you make the decision.

    Reply
    1. AvonLady Barksdale

      DEFINITELY in agreement with your “Two”. She’s a great woman, she’s right there all the time, she’s cool… but the drama potential is so high, I wouldn’t risk it before weighing all the options. Get out there and date a bit, and see if she’s superlatively awesome or just great and happens to be in front of you.

      Reply
    2. TheEmployee

      I’ve turned down a couple of women in those 5 years. I haven’t been devoid of attention, just nothing with mutual interest. The pieces haven’t fit with anyone until now

      Reply
  15. heather

    If you’re going to do this, you have conduct yourself impeccably at work. You can no longer afford to spend a quiet half an hour slacking. You’re now employee of the month every month. It becomes very awkward to have to reprimand your daughter’s boyfriend, or to know that your dad and your boyfriend had that kind of interaction.

    Signed, someone who met her boyfriend in their shared office the week after her father had put him on a PIP.

    Reply
      1. heather

        It was all fine! We’re not in the US so a PIP isn’t quite as close to a firing as it might seem. My boyfriend had been going through a difficult time, he resolved it and became an excellent performer. That was fifteen years ago, and he’s the only one of us still working there. My dad is retired, and babysits our child.

        Reply
    1. TheEmployee

      I’m actually the most well paid and popular employee we have. Many of our clients are here only because I am, and it has become something of a running joke that we don’t need the other people in on days I’m here.

      My desk gets probably 60-65% of the business, even though there are four people in at a time.

      Reply
  16. ABK

    Normally this would be weird, but sounds like you and her are already really good friends so you have an idea of how this would work. Do you already hang out with her family outside of work? Do you have a reason to believe that her dad will get involved in this relationship or react particularly badly about any part of it? It seems like it should be fine if he can act like an adult and not get all possessive over his daughter.

    Reply
    1. ABK

      i’m gonna adjust this answer. You have a good feeling about her, you haven’t dated much lately, and you’ve been at this job for 5 years. How about get a new job and then you can pursue the gal. Change it up, both your job and your romantic life!

      Reply
  17. SleepyTimeTay

    I feel like this is a thing of “don’t sh*t where you eat.” Unless you plan on changing jobs in the very near future, don’t do it. It may work out, but then favoritism with the boss comes into play and if the relationship doesn’t work out….well, it could ruin the job you love.

    I do want to wish you the best with whatever you choose!

    Reply
  18. foolofgrace

    I would only do it if I had enough money saved up to survive on for a few months in case things go south. Just be prepared for the contingency that you might have to leave the job, and then … go for it. And in the putting-cart-before-horse category, she might not even want to go out with you anymore. Maybe she has a boyfriend, maybe she figures “He rejected me once, I have to reject him back”, maybe other scenarios. Make sure you have a place to land, and then … leap!

    Reply
  19. Jubilance

    She’s your coworker AND also your boss’s daughter?

    That’s two big red flags for me. If it ends badly then you not only have to work with your ex, but also your ex’s parent…who is your boss. I’d love to think that everyone would be professional and put personal feelings aside, but I doubt that could happen.

    Unless you’re going to change jobs…I wouldn’t do it.

    Reply
    1. Antilles

      You didn’t even mention the third (and biggest) red flag: “I’m a recluse who hasn’t had a real girlfriend in five years. It’s not as though I feel confident in just moving on to the next opportunity because I honestly don’t know where that could possibly be.”
      This is harsh to say, but as someone who’s been there, I can assure you that the “she’s the only option” mindset drastically increases the odds the relationship will end badly.

      Reply
      1. Jadelyn

        This, so much. Because that mindset doesn’t necessarily go away once you’re in a relationship – you wind up hanging all your needs and hopes and fears on this one person because you think if they leave you you’ll never find another opportunity for love again. Which is all but guaranteed to either scare her off, or produce relationship burnout after a couple years of her managing all your emotional needs.

        So *if* OP decides to go for it – and I wouldn’t recommend it, because dating a coworker is bad enough, and dating your boss’s daughter is bad enough, but dating a coworker who is also your boss’s daughter just sounds like a minefield of Nope; but of course, it’s OP’s decision in the end – please make sure you’ve got your own head on straight before you do. Get therapy if you think that will help, make an effort to develop other friendships and relationships outside of work and a single romantic partner.

        Reply
      2. spock

        I didn’t read it as “I only want to date her because she’s the only option”. I think OP is just saying that it’s not as easy as “just go date one of the many other people you’re interested in and may be interested in you”. It doesn’t mean they’re not truly into her, it’s just a reality that dating is harder/rarer for some.

        Reply
        1. ArtsNerd

          Right, it’s possible the OP is in the “it’s her or a lifetime of loneliness” mindset which is a very real and common trap, in which case all of the above concerns stand.

          As someone who rarely dates, and rarely feels strong romantic connections with other people, I interpreted that phrase the way spock did. If I feel a connection with someone, I don’t walk away from it lightly. I’m also perfectly comfortable with the tradeoffs of being single vs. partnered, and am neither “lonely” or “desperate.” There are a few recent articles discussing that trend/societal shift, but I’ve linked to the one my user name that speaks to me most: “I Never Thought I Would Find Love. And Then I Didn’t” on Reductress (NSFW elsewhere text on the site, including headlines.)

          Reply
          1. ArtsNerd

            Given more thought, I think I’ve been projecting a lot of my own internal thought processes onto this letter. I’m switching my loyalties to team “Expand Dating Pool” if the employee has any kind of trouble navigating conflict or awkwardness, which is true for more people than not.

            Reply
      3. TheEmployee

        She’s not the only option. I’ve turned down a few options in these five years.

        People have been jumping hard to this conclusion in the comments though.

        In reality, I just dont like many people, and I don’t attract many people in return. But this is the rare case.

        Reply
  20. anycat

    this happened at a friend’s company – they ended up getting married. but on the flip side you have to have a plan b if everything goes to hell.

    Reply
  21. kb

    Before you do anything, I would ask yourself some questions:

    1) Do you have an in-demand skillet that would allow you to find another job quickly?

    2) Do you treat the women you date with respect?

    3) Did most of your past relationships end on okay terms or did they blow up?

    4) Are you a good or excellent employee? If you’re fired or tension arises between you and your boss, that may make the relationship awkward.

    5) Are you willing to take this relationship really, really slowly and seriously?

    Reply
    1. Gerber Daisy

      I realize it was a typo but asking whether you had an in-demand “skillet” and whether it could help you find another job quickly made me laugh. Which I greatly needed this morning!

      Reply
      1. kb

        Oh no, you’ve discovered my secret: if you show up to any job interview with an in-demand skillet, you are immediately named CEO of the company, no questions asked

        Reply
    2. SierraSkiing

      That’s a good list! Also a couple more, along the same lines but about her:

      1) How does she talk about her exes (if she does talk about them)? If you broke up, how would you feel if she talked about you that way to your coworkers?

      2) How protective/involved is her dad in her romantic life (ie, joking about sitting on the porch with a shotgun)?

      3) In your experience, how good is she at setting her feelings and professional life apart?

      Reply
    3. Christmas Carol

      6) How would you respond if/when you never approach her and she meets another Mr. Right, or even worse, gets tangled up with a Mr. Wrong?

      Reply
    4. Just Employed Here

      6) Are you actually genuinely attracted to this woman, or does she just fit the idea of someone you should think would probably be a good partner for you?

      I wouldn’t start dating someone just because we got along extremely well and had a lot of the same hobbies, but maybe that’s just me. (For the record, I do work in the same ~30 person company as my husband, but we were already married when first I and then he started working there many years ago.)

      Reply
    5. Iris Eyes

      I’d also add
      12) Are you both (+Dad) willing to set and maintain boundaries while working?
      – At work you aren’t dating, you are coworkers. Outside of work you aren’t coworkers you are dating

      It can be really telling to see someone’s work ethic, that’s part of what attracted my first BF and I to each other (we were coworkers, teenagers, and didn’t maintain boundaries as well as we should have)

      Reply
      1. zora

        This is the main one I was thinking. Are you both mature and able to be really thoughtful about this and any problems that crop up, and able to be very upfront about boundaries?

        I would say it makes it a little more awkward because when you are JUST starting to date, you have to have some complicated conversations a lot sooner than you would normally. Especially conversations about what would happen if we are having a fight at home and the flip side, a disagreement at work. It’s not impossible, but it will be much better for you in the long run if you are able to talk about these things early and often.

        And if you don’t think one or the other of you is able to do this very intentionally and maturely, THAT is when I would think twice about whether this is a good idea at all.

        Reply
    6. Meliza

      Everyone should have an in-demand skillet!

      But seriously, these are great questions, and a good suggestion for the OP.

      Reply
    7. TheEmployee

      1) I am under that impression. I have amassed tons of references and am finishing my grad degree.

      2) no I’m a horrible monster. A ramsey bolton mixed with a late-era Homer Simpson through and through.

      3) I’m friends with several of my exes.

      4) I’m recognized as the most important employee at my job by my co-workers and our clients.

      5) what do you mean?

      Reply
  22. an infinite number of monkeys

    At one point in your letter, you refer to your boss as “our boss.” Is she his direct report too?

    I won’t say “oh nooooooooooooo” but would proceed with extreme caution, and do be prepared to leave the job even if things go well, because the dynamics will be awkward.

    (Where I’m coming from: I started dating an immediate coworker – we report to the same boss – after working with him eight years. We’re now married. So I am obviously not opposed on general principle. But our boss is not his mom, and much as I adore my husband, that might just have been enough to put the kibbosh on things.)

    Reply
  23. AnonEMoose

    I’ve never been a fan of dating coworkers, personally, although I know that many people do and it works out fine or even beautifully. That said, you are not me, and you both get to and need to make your own decisions about this (as, of course, does your coworker).

    What I would suggest is this – I believe that the Paging Dr. Nerdlove blog, and possibly Captain Awkward(?) have some past entries on dating coworkers. I’d suggest doing some reading in their archives, and doing some rigorous thinking about issues such as: How will I handle it if she says no? If she says yes, can I remain professional during work hours, no matter what is or isn’t happening in our relationship? Do I have (or can I create) an exit plan for if things end badly?

    If you do ask her out, please do her and yourself a favor, and be clear that you are asking her on a date. Don’t do the “Schrodinger’s Date” thing, where you ask her for coffee or lunch or something, and act like it could be just work friends or a date…that’s not cool, and not fair to her. Use your words and let her know that you think she’s great, and if she’s interested, you’d like to take her out for (insert fun activity here).

    And if she says no, your feelings about that are Not. Her. Issue. Be prepared to go back to being cordial coworkers if that ends up being the case, although it’s fine and understandable if you need to be distant for a bit to deal with your feelings. You still need to be professional, but you can cut back on non-work interactions for a bit.

    If she says yes, be chill about it at work. Make sure you respect her boundaries in both the work context and the romantic one.

    No matter what you decide, I wish you luck, OP!

    Reply
      1. oldbiddy

        + 2. Schrodinger’s Dates are a piss poor option for most people. If you have a history of getting into relationships with people in your circle of friends, go for it – you’re sending and receiving the right signals for it to work. But if you find yourself frequently on either end of a Schrodinger’s date, it’s time to rethink your dating strategies and jump into asking people out on low key dates early on or doing internet dating.
        I wish I’d learned to “return the awkward to the sender” at an earlier stage in my life

        Reply
    1. clairels

      Maybe I’m in the minority here, but as a woman, I actually prefer a Schrodinger’s Date-type-invite, because it takes the pressure off. As an adult, I think I’ve been around the block enough to know when someone has romantic intentions without them stating it flat-out. A guy literally asking, “Do you want to go out on a date?” would kind of creep me out and make me think that he’s planning on moving way too fast.

      Reply
      1. Let's Talk About Splett

        I agree somewhat, however, back when I was much younger I got ready and showed up for what I thought was a date with a crush, and it became clear right away that he just wanted to hang out as friends, and I felt ridiculous.

        Reply
      2. AnonEMoose

        I think you might be in the minority, although I can understand the logic. But for me, I’d hate the ambiguity of “is this a date, or just friends hanging out?” And I’d really hate thinking it was the latter, while the guy is thinking it’s the former, and then have him make a pass I’m not mentally prepared to deal with. (Although I admittedly haven’t had to deal with dating in a long time…something for which I am regularly and profoundly grateful!)

        Plus, this is a gambit that too many guys use, and then complain about being “friend zoned” if it doesn’t work out the way they want. So to me, it feels pretty toxic. And in this specific situation, I think clear communication is really, really important because of the work factor.

        Reply
      3. blackcat

        I’ve been partnered for 10 years now, but back in the day, I was the victim of several Schrodinger’s dates. I actually didn’t mind so much when it was low-stakes–eg dinner in the dining hall in college, coffee, lunch. But what I thought was a going to be a group of friends going to dinner and a play? Yeah, that was super awkward. I ditched on dinner. I had been looking forward to meeting these friends of his who supposedly shared my theatrical interests! I was new in town, and it sounded like a fabulous plan. What was most baffling was that this guy knew I was partnered and it sounded like the initial invite was for me + my partner (maybe it was? like he would have brought a group until I told him my SO couldn’t make it, but I was excited? IDK).

        Reply
      4. Not a Mere Device

        It feels like there are two or three different kinds of Schrodinger’s date, though: asking someone you know in a non-work social context “would you like to get a cup of coffee?” or “would you like to have lunch with me at the new Chinese restaurant downtown?” is clearly an invitation to spend time with one other person, socially. With a coworker, that suggestion of a cup of coffee, or lunch near the office, could be either a date or a planning session for the llama breeding program. It’s only fair to specify that this is a social invitation–even if you don’t say “date,” it’s not fair to set up a situation where someone feels they have to say yes because the llama project is overdue, if you really just want to socialize. Or for you to be thinking “we can talk about movies” while they’re desperately carving out half an hour to review the llama files.

        Trying to trap someone into a date by pretending that one is organizing a group event, then springing the “surprise” that everyone else cancelled, but we can still see the movie/go to the pizzeria/etc. is just wrong. It’s unethical, and it’s unlikely to lead to a happy relationship, even if the target goes to the movie with the plotter. There’s a difference between not specifying “this is a date” and actively lying to the person you want to date because you suspect that she doesn’t want to go out with you, and try to trick her into doing so.

        Reply
    2. TheEmployee

      More than anything, I’m fixated on the fact that this responder thought they should give me advice on how to handle being rejected without making a jerk out of myself.

      Reply
  24. Kittymommy

    I’m less concerned about her being a colleague than her being the boss’s daughter (assuming it’s a different department though). If the relationshi OP goes really well (marriage, kids, whatever) or really bad (nasty breakup) you’re probably going to need to find a new job. If you’re good with that, go for it!

    Reply
  25. RandomusernamebecauseIwasboredwiththelastone

    I thought we’ve established that if the scenario being asked about has been a plot of a movie or sitcom, it’s a bad idea.

    Reply
  26. Decima Dewey

    No, at least not while you’re still working there. What happens when you and she have your first tiff? Will your coworkers see favoritism in every interaction with your boss? Or will they seize on minor friction as “uh oh. All is not smooth!” Too much can go wrong here.

    Reply
  27. Student

    No. Don’t do this.

    First off, you are considering doing something that YOU already think is a bad idea. Listen to your own gut here. It kept you from doing something that you don’t think you can pull off successfully before.

    Second, you are thinking of doing something you think is a bad idea because you’ve gotten desperate for a girlfriend. You know what you should do when you are desperate for a girlfriend? You should get a practice girlfriend for a low-stakes, likely temporary relationship. Clear your head, get some refresher practice at being in a close relationship. You should not jump into a high-stakes relationship that could jeopardize your employment under those circumstances. You aren’t thinking clearly, you aren’t weighing the risks vs benefits, you aren’t thinking at all about how the woman involved will deal with the same risk vs. benefit issues. You aren’t thinking about what you can do to make her life better, what you can offer to her as a partner.

    Third – interests in common are nice, but they aren’t actually what makes a relationship successful. What makes a relationship successful is positive interactions. You don’t need to date a female copy of yourself to have a successful relationship. You need to have positive interactions, you need to care about her, she needs to care about you. You need to be able to communicate about big issues. You’re terrified of communicating with her about the huge issue – your boss – that will be the elephant in the room every day. That does not bode well at all. You need to be able to have that discussion repeatedly for this relationship to go anywhere.

    So go out and date somebody else instead. After that, think about these issues and whether you can tackle them. If you can, then go ask her out.

    Reply
    1. JLCBL

      A “practice girlfriend”? Is this a term people use? Because it sounds…not very considerate at best and pretty sexist at worst. Go out and ask someone you’re not really interested in seems like iffy advice for a self-described recluse.

      Reply
      1. AnotherAlison

        I agree the term sounds awful, but I think advice to perhaps casually date some different women is not so bad. I’m getting old, so most people I know who are in the dating game are divorced, but the trend I see is that they go on several first/second dates in the same couple of months, then they settle in and date one person for a few months, then that doesn’t work out, and they repeat the process a couple more times until they find someone who becomes a long-term partner.

        Reply
        1. JLCBL

          Yes, I am in agreement with the several people who advocate going on a few dates, and the idea of it being lower stakes and perhaps short-term. This advice includes “refresher practice at being in a close relationship” which is not the same thing, and frankly sounds like treating an (admittedly imaginary) third party as disposable.

          Reply
        2. Manders

          Yes, agreed that this is a pretty normal phenomenon. In my observation, it’s a particularly good thing for folks who tend to fall rarely and hard for people to get used to going on casual dates. And it’s often the case that a relationship that starts with casual dating turns into a healthy, long-term love without the years of pining and building up a perfect image of the object of their affection.

          Reply
      2. RandomusernamebecauseIwasboredwiththelastone

        Eh… I think rebound is a more common term, but it’s common enough as both girlfriends and boyfriends.

        Reply
      3. JanetM

        I don’t know that it’s any worse than a “rebound girlfriend” (speaking as someone who met her now-husband while rebounding from a very complicated relationship. And who dated several guys with the up-front understanding of, “I’m not looking for long-term, but we like each other and have common interests. Want to date for a while and see where it goes?”) For what it’s worth, I’m still on good terms with all my past boyfriends.

        However, I never dated where I worked, much less the boss’s son, so I can’t speak to that issue.

        Reply
      4. Tuxedo Cat

        I’ve never heard of that term, but I have heard people talk about “starter wives.”

        Maybe reframe the advice in more positive terms? The OP should try dating other women who may not be a 100% match initially on paper. Still should have some important things in common but they may not have everything, at least on the surface, in common.

        Reply
      5. Student

        This is how I approached dating (men) initially. Especially in high school and early college. Maybe I was the only person on Earth who had no expectation that any guy I dated was going to become my husband, though. I thought it was a healthy attitude for a teenager at the time, and for anybody who doesn’t actually have much dating experience; maybe I was just a sexist sociopath.

        It’s less of a “I’m using you for your body” and more of a “I’m trying to figure out how relationships work, and what things I care about in a relationship. I am going into this relationship with the explicit expectation that it is not to find a forever-husband, but to find someone I enjoy spending social time with. It probably won’t work out long-term. I’m not going to vet this person to the 1000th degree for marriage immediately, and I have standards that are important to me and non-negotiable but I’m going to accept some slack on standards I might otherwise hold a potential husband to.” Like, I’m not going to date a guy who hits me (very serious standard), but maybe I’d date a guy who smokes when I wouldn’t want to live with a smoker forever, or somebody who doesn’t have the long-term economic/career prospects I’d prefer.

        It’s more about not being super-picky and not over-investing in the relationship right away, and giving myself space to call it off whenever I want. My husband graduated from practice-boyfriend to fiance to husband, so it’s not like there is an absolute hard relationship wall that you have to trow in front of it.

        Reply
    2. annakarina1

      I don’t like the idea of a “practice” girlfriend or a temp one, because in my twenties, I was close friends with a guy who was into me, and when I didn’t feel the same romantically, we had this close platonic friendship, but he’d ditch me whenever he got a real girlfriend. This was a pattern of rarely seeing me whenever he was in a relationship, then using me as a placeholder in between girlfriends. It frustrated me because I didn’t like being used like this, and wanted to still be good friends when he had a girlfriend. He’s engaged now and we only talk through occasional texting, but it still sucked to be treated like that. He shouldn’t treat a woman like that, it’s unfair and callous.

      Reply
      1. Student

        That’s more about honesty than anything else. Your guy wasn’t honest with you, you weren’t honest with him, and possibly you weren’t honest with yourself. I’m not advocating leading on any practice girlfriend by promising her the moon and the stars and a house-full of babies with a white picket fence. I’m advocating exactly the opposite, really.

        If your guy had told you he wasn’t going to stay with you long term, you could’ve decided for yourself whether you wanted what he really was offering you – a temporary practice relationship, or a placeholder spot between his real interests. If you’d, perhaps, been a bit more aware of the pattern and a bit less invested yourself into making him a long-term prospect, then maybe you would’ve drawn the line with him sooner. It’s not actually wrong , or unfair, or callous to have those kinds of relationships – but it’s wrong to promise or imply one type of relationship (long-term marriage prospect) when you’re really pursuing the other type (dating for strictly fun, or practice, or sex, or whatever short-term pursuit).

        Reply
    3. Let's Talk About Splett

      As a huge feminist and someone who recently got back out there after being single for a really long time, I think some people are taking the “practice GF” thing here too literally. I took it to just mean someone to date casually in a low-stakes way. In a real way being on a date is something you need to get used to doing again. Because you can’t just stop texting your coworker/boss’s daughter back if you don’t want to keep seeing them.

      Reply
      1. LBK

        Yeah, I don’t love the term itself but the idea is pretty sound. It just means that the OP should date casually a little to make sure it’s really about *this* woman and not just *a* woman, since it sounds like there might be an element of convenience here that’s making her seem particularly appealing.

        Reply
  28. Pancakes

    I wouldn’t do it. There are obviously so many issues with dating your boss’s daughter who is also your boss, and it doesn’t seem like OP is all that into her. OP mentions that they have a lot in common and that they don’t meet a lot of potential partners, which isn’t exactly the kind of declaration I’d want to hear from someone I was going to get into a potentially sticky dating situation with. It doesn’t seem like OP likes her so much that it is worth taking on this kind of risk. But if I’ve misread this and the OP feels very strong romantic feelings for her then I’d say it might be worth going for.

    Reply
    1. TheEmployee

      I tend to explain things in a very mechanical way. I also avoided saying “omg she’s the one ohhhh” because I wanted something substantive.

      Sharing interests with me is not a common occurrence. She wants to study the same obscure bs in college that I love to learn on the side. And vice versa.

      Reply
  29. The Original K.

    I found out after the fact that my mother’s friend & colleague tried to set me up with another of their colleagues. My mother was the guy’s boss. He was apparently all in (saw my picture, liked what he saw, liked what she said about me) until he found out I was his boss’s daughter, and then he was like “NOPE.” When I found out, I said “I can’t say I blame him.” I would never date my boss’s son unless I was quitting (and even then I’d only do it once I was out the door). I’m team “no, unless you’re planning not to work there” onthis one.

    Reply
  30. Jenny

    Assume that even if it’s a match made in heaven and your boss is supportive, you’ll eventually want the boundaries and independence that come from having your job separate from your wife and in-laws. So, start working out what that job might be. (That thinking and research etc is a win for you no matter how anything else may turn out.)

    Also, you can *tell* your co-worker that you are interested but concerned about the overlaps, and see what she says… if she’s not interested anymore, you can move on, and if she is, rather than asking her out, see if you can handle some conversations together about navigating the overlaps (if you can’t, put the brakes on or get a new job before doing anything else).

    Reply
  31. ENFP in Texas

    Not only “No”, but “HELL no.”

    That is a can of worms that you do not want to open.

    If you want to date her, you need to not be in a direct line of report to someone who pays you and has control over your career.

    If you’re serious about her, see if you can move into another department where you’re not working for her father.

    Reply
  32. Forking Great Username

    My main concern is that the follow up letter could read, “My girlfriend and I just broke up. Problem is, we work together, so I still have to see her every day. Things went pretty badly towards the end, and I know she has told her parents about it and they’re upset with me too. That leads to my bigger problem – my boss is her dad. Now he’s writing me up for every little thing. I want to find a new job and quit, but there’s no way my ex’s dad is going to give a positive reference considering the situation. What should I do??”

    Yes, I realize there’s an alternative where they’re all adults about it, and if they break up and OP is looking for another job, dad/boss gives a fair reference. Personally, that’s too big of a risk for me to take. Although in my early 20s I probably would’ve just went for it, so I’d say it depends on a lot of factors – your boss and his general personality/disposition, what stage of your career you’re in, if you have money saved or some kind of support of this goes badly, if you really think this girl is “the one”, if you’re prone to relationship problems and drama, etc.

    Reply
  33. Millennial Lawyer

    Maybe this is out of line, but your description of why you want to date her “I’m unattached, and the aforementioned coworker is still here. We get along extremely well and I honestly don’t know if I know anyone that I have more in common with. She’s remarkably intelligent, enjoys the same academic subjects that I do, the same hobbies, etc.” doesn’t sound super compelling to me? It almost sounds like you’re figuring you’re single, you get along, why not try it out? But the stakes are a lot higher if this is your boss’ daughter. You have to really be so interested in her that you’re willing to risk your job to have the opportunity to start a serious relationship with her. This is not a fling sort of thing.

    Reply
      1. Millennial Lawyer

        Exactly!!! Imagine being turned down, the guy finally asks you out and realizes he was wrong, and then three dates later decides he wasn’t really “feeling it.” Yikes, I’d go straight to my dad. LOL.

        Reply
    1. ArtsNerd

      Hmm, ok this is true. I’m projecting a lot of self-awareness and ability to navigate awkwardness onto this letter writer that they do not necessarily possess. I’m switching my loyalties to team “Expand Dating Pool.”

      Reply
      1. Millennial Lawyer

        It’s totally possible I’m projecting as well – it came off more young and bro-y than socially awkward to me, but even if it is more of the latter, I’d be more swayed if instead of “I’m unattached and we get along well” we were hearing “I think she’s the greatest and I’d really love to date her.”

        Reply
        1. ArtsNerd

          Right! I initially extrapolated that “rational” description of their compatibility as a way to make it clear it’s not just a hormone rush or anything, and to make it fit into a more professional discussion. But even then, I’m not getting the “she’s the greatest” subtext on a re-read, and that’s pretty key.

          Reply
          1. TheEmployee

            Artsnerd is correct! Thats just how I talk abour things.

            I… Uh… Have been described as very mechanical.

            Reply
            1. TheEmployee

              And by correct, I mean the description as to why I talked about her in very unembellisshed terms. I was describing the rational reasons for why I like her, instead of “oh she’s so great and pretty and did I tell you she’s great?”

              Reply
              1. Nonsensical

                It still feels like you’re pushing too much. I am on team expand dating pool. Find some hobbies and get out there!

                Reply
  34. Tina Belcher's Less Cool Sister

    I’m on team don’t do it. There’s just too much potential for messiness. Besides the obvious (it doesn’t work out so you have to find a new job), can you really expect your boss to give you a fair evaluation when you’re dating his daughter?

    Even in the best case scenario, where everyone is mature about it and he does his best to treat you like every other employee, there’s no way to avoid your boss learning personal details about your life that you might otherwise not want him to know. Assuming she’s reasonably close with her family, you’d either be crossing way way over the boundary of normal professional relationships here and your boss is suddenly privy to intimate details of your life, or you’d be asking your girlfriend to fundamentally change the nature of her relationship with her parents and not talk about her relationship. I know for me, I’m not even particularly close with my parents but my mom knows about my fiance’s work life, professional aspirations, vacations we’ve been on, our plans for a family, etc. And whatever my mom knows, I have to assume my dad knows too.

    Plus, do you really want to spend holiday dinners and summer vacations with your BOSS?

    Reply
    1. Oilpress

      And the coworkers…I guarantee there will be some side-eye and bitterness toward the OP with assumptions of favoritism. Anything the OP earns at work will now be under question from his colleagues.

      Reply
  35. Lurking Tom

    I’m usually an optimist, but I think it would be wise to consider the worst case scenario of a horrible breakup in this case.

    – You’d still have to work with the person you had a horrible breakup with
    – You’d still have to report to the person whose child you had a horrible breakup with
    – To avoid those things, you’d need to leave your company or transfer to another department

    How it all plays out is very much dependent on how closely you work together, how you & she each handle yourselves at work, how your boss handles it (maybe he takes a “they’re adults, things happen” approach, maybe he’s a very protective/helicopter parent who has no qualms about bringing personal feelings across professional boundaries). There’s really no way any of us can know the personal dynamics at play here. I think in an ideal world, people should be able to keep personal & professional relationships separate and not have one negatively affect the other. But it really heavily depends on the people involved.

    Good luck to you whatever you decide!

    Reply
  36. StressedButOkay

    Oohh, yeah, I’ve been in both a situation where I did date a coworker (and it ended very, very badly) and where a coworker and I were clearly attracted to each other.

    I think you need to figure out first if she’s even still interested. You mention that she was aware of your feelings last summer but you turned her down. Obviously she’s fine with that as you’re close friends now but I would absolutely see if she’s still interested! Being super close as friends does not = still interested romantically, especially after she already asked you out.

    Then – yeah, this could go very well or very badly. It’s not an automatic reason to change jobs but it will shift the dynamic in the office a lot if you two start dating. Depending on the hierarchy, it could throw a lot into question.

    I learned my lesson and I don’t think I’d ever pursue a relationship at work – or at least not with someone in my department again – but it does work for some people. You just have to approach it very, very carefully.

    Reply
  37. do it do it do it

    YES.

    Can you see a future with this woman? Can she see a future with you?

    Which would you prefer in 60 years; to have her by your side, or to have a nice long career at this company? Neither is guaranteed, whatever you do, but life and love take priority over work.

    Reply
  38. Susan Sto Helit

    A friend of mine works for his girlfriend’s father. He really likes his job. He’s not so into the girlfriend any more, but he also doesn’t want to have to uproot his entire life in order to escape his relationship, so he’s currently ‘settling’.

    I think my friend is doing everyone involved a disservice here.

    Everyone’s job is different, and everyone’s relationship is different, but be sure you think about all the potential consequences before you make a move here. And be sure you’re not doing it just because you want to be in a relationship, and she’s an option. That’s not a good enough reason.

    Reply
    1. Julia

      The poor girlfriend. :(
      I wonder if the woman in question here ever considered this scenario. Personally, I even worried about lending my now-husband money because I was afraid he’d string me along until he could pay me back (we had a contract – and things worked out just fine!), but I’m pretty anxious when it comes to romantic relationships.

      Reply
  39. Bea

    I’ve seen dating at work work well when both people are rational reasonable humans. It’s hard to know before you wade into the water but given the time you’ve known her and it seems like you’re both seemingly reasonable(and she threw the line out first…)

    Whatever whatever it worked for HHH and Stephanie McMahon. I’m all about following your heart and instincts.

    Reply
  40. WCF

    I would advise against it. First of all, as it has been discussed here before, workplace relationships are not always advisable. The falling-out of a relationship with a coworker is part of the reason why I left my last job, despite the fact that we were very professional about it and remained friends afterwards (and despite the fact that I promised myself I’d never let a relationship affect my career). Trust me, it doesn’t matter who you are- it’s hard to break up with someone and then see them every day.

    Also, don’t underestimate how potentially awkward this could be. For example, meeting your girlfriend’s parents for the first time is usually awkward, and hanging out with your boss outside of work is usually awkward. Now imagine combining these two events…

    Reply
  41. Some Guys Call Me Shawna

    Is this a small or family-owned business? The fact that the boss’s daughter is working at the same company as her dad already seems pretty unusual.

    Reply
  42. Glomarization, Esq.

    I’m a recluse who hasn’t had a real girlfriend in five years.

    Work on this issue so that you open up your pool of possible romantic partners. In the meantime, do not date the boss’s daughter.

    Reply
    1. Happy Temp

      Yes, I agree. I was on the fence about this until I read “It’s not as though I feel confident in just moving on to the next opportunity because I honestly don’t know where that could possibly be.” That tells me OP is just picking what seems convenient and close-at-hand, not that OP genuinely, truly feels passionately about asking this person out.

      OP, you’ve gotten a lot of great advice! I agree with those saying work on yourself first and your dating life second before going forward with asking her out, with full understanding of the potential negative consequences.

      Reply
    2. Zillah

      I don’t think it’s necessarily that easy, though – just saying “work on this” isn’t really actionable advice.

      Reply
      1. Glomarization, Esq.

        Well, heaven forbid I say instead “get therapy,” which would have had the commentariat jumping on me. To clarify, I think one of the issues here is that, as a self-described recluse, the LW has few, if any, other women in his circle of acquaintances and co-workers, so he has likely glommed onto this particular woman as The One And Only Forever And Ever as a romantic partner. My suggestion is to work on the problem of being a recluse — I’m not a doctor or therapist, nor am I a person who would describe myself as a recluse or former recluse who has overcome a recluse problem, so I don’t have action steps to suggest — because LW needs to have more women in his life so that he’s not so focused on this one woman as the answer to the lack of a romantic partner in his life.

        Or, to be more concise, the question was “should I date the boss’s daughter” and my answer was “no.”

        Reply
      2. Close Bracket

        ok, here are some specifics for the OP:

        Get out of the house. Get coffee. Go to the library. Go to movie. Join MeetUp groups. Join a dating site.

        Working on not being a recluse and/or not having a girlfriend is plenty actionable.

        Reply
    3. Bea

      Reclusion is often a subset of anxiety and other issues. I know because I’ve been there only less reclusive in terms of only leaving the house when necessary. I did and still do a lot of solo long drives. But I do not connect well with others in most social settings.

      That said I found my soulmate in the end. So to the OP there is hope but you do absolutely have to accept risks associated with any romantic relationships and opportunity.

      I almost settled but thankfully (now not then then was tragic to me) the other party pulled out of the setup. Therapy did help me but like most mental illnesses and substance abuse etc, you have to want help. Nobody can do the hardest part for you, which is wanting to change and working on it.

      Reply
  43. yet another Kat

    You mention that you love your job “more than most anything.” That’s honestly a pretty rare way to feel about a job, and not something you should take lightly or risk losing without a LOT of thought. Someone above mentioned that it’s possible that your interest in this woman could be at least partially a question of proximity. That’s also something to think about – is she really the one for you, or does it seem like it because she’s the one who is next to you every day?

    All that being said, if the way you feel about her is worth losing:
    – your job
    – your friendship with her
    – your positive relationship with your boss (future references, etc)
    … then go for it!

    Reply
  44. Libervermis

    Based on the letter the OP has a number of questions to sort through, including whether the boss’s daughter is even still interested. I notice that the situation is framed as “I’m unattached and she’s still around” as opposed to “I’m really into her and she’s been flirting with me” or “I’ve been thinking about her a lot”. OP may have just left their feelings out of the letter, and getting along well with someone who shares your interests is a lovely foundation for a romantic relationship, but it seems the potential risks (assuming she’s still into the OP) are pretty high for an idle “well, I spend my workdays with so-and-so, maybe we could make a Thing of it”

    If OP decides that the possibility of needing to find a new job is worth it and the crush is also interested, then *she* needs to be part of the conversations about how/whether it will work.

    For what it’s worth, I do think that a situation where the relationship goes really well, everything is great at work, and things with boss continue totally rosy is…less likely than at least one of those elements changing in some way. That might not be a bad thing! But the chances that this particular relationship will just slot painlessly into OP’s current life don’t seem all that high to me.

    Reply
    1. Frankie

      Agreed, and I’m surprised others haven’t mentioned it–just because she’s still there doesn’t mean she’s still available! Or that she’d agree to give it a second go if she’s been rejected once. Not to say OP doesn’t have a shot, but the letter kind of skips that part and it’s important.

      Reply
      1. Let's Talk About Splett

        It actually makes sense given the dynamics for him to ask her out if she HAD left!

        Reply
  45. Secretary

    If you’re going to do this, don’t do it like you’re “getting with” her or inviting her out to drinks and trying to get it to turn into something more.

    The only way to start this with her respectfully is to ask her out on a real date using the words “can I take you on a date this weekend?”

    Then on that date, use the time to get to know her and whether you can see potential for something long term with her. If you can, take it reeeeeally slow. If you can’t see a future with her, don’t waste your time continuing to date her and ask out other women.

    Reply
  46. Lurker

    Don’t fish off the company pier.
    Don’t dip your pen in the company inkwell.
    Don’t isht where you eat.

    If you or she (or the boss) leave the company, or if you get a different boss, fine. But otherwise this seems like a very bad idea.

    Reply
  47. I Wrote This in the Bathroom

    Adding my voice to the chorus of “no”. If it helps, FME, having the same hobbies and liking the same academic subjects means close to nothing as a predictor of a long-term compatibility as a couple. Made that mistake once. It was a toxic and unpleasant relationship. But we liked all the same bands!

    Reply
  48. Lady Ariel Ponyweather

    1. What does she think about this situation? Have you two spoken about the issue that she’s the boss’s daughter and the difficulties that could bring? How you both would handle a break-up, or if you went on a couple of dates and realised the chemistry isn’t there?

    2. This part jumped out at me:

    On the other hand, I’m a recluse who hasn’t had a real girlfriend in five years. It’s not as though I feel confident in just moving on to the next opportunity because I honestly don’t know where that could possibly be.

    Let’s take work out of it. Romantic relationships take up a huge amount of time and energy. Are you ready to commit to that? I don’t know your personal situation (and aren’t asking you to share, don’t worry). It’s that you mention being a recluse, and I’ve known a couple of people who pretty much stopped dating because they found they valued their alone time far too much. A romantic relationship was too demanding, both emotionally and time-wise, and they decided it wasn’t fair to themselves or the other person.

    You might need to start by being absolutely clear on whether you can commit to pursuing a romantic relationship with her. Can you share your time and personal space? Can you give up an evening a week to do something together? Are you willing to open yourself to her emotionally and be vulnerable with her? Are you willing to accept her flaws and vulnerabilities? It’s those kinds of questions you might need to answer first (and she might need to do the same).

    3. If you’re pretty sure that yes, she’s worth taking the risk (emotionally and job-wise), would a group social outing be an option? Getting to know each other outside of work but as part of a group might help you both decide whether you’ll click as a couple. Who knows, you might find you’re better off as friends, or that she has a gross habit you can’t stand, or you just don’t click.

    Reply
  49. Zuzu

    I say go for it. My parents met at work. My husband and I met at work. And our story is at least as weird as dating the boss’s child. Our boss was like a surrogate father to my husband and he (the boss) also tried to recruit me to be his mistress (he was married) got jealous of my husband when we started dating and fired him. We both chucked that boss and that job and lived happily ever after!! I sure wouldn’t trade my wonderful relationship for success at that job.

    Reply
    1. Bea

      Omg this incredible love story. I’m glad you both rode off into the sunset. Barfing at the gross boss dude, not a mentor or a boss to keep!

      Voldemort fired my SO and tried to convince me he’s a liar “would you believe is claims if you didn’t know him?” (the response is yes, they were truthful claims and a stranger wouldn’t have changed my trust WTF.) I just can’t with scummy bosses.

      Reply
      1. Zuzu

        Ugh, my terrible boss also tried to badmouth my now-husband to me (to convince me not to date him- he felt himself to be a more suitable romantic partner for me despite being married, old enough to be my father, and having mentored my husband for six years)
        This also was a farm rather than a traditional office, and we all lived on site. So that added to the total lack of boundaries.
        We actually did ride off into the sunset- we escaped that boss by hitchhiking away over a mountain!
        I sure wish I had known about AMA back then!

        Reply
        1. Bea

          Omg this could easily be made into a romantic novel. Let’s just change it to the 1800s for my own sick pleasure please!!!

          I’m not even surprised since farm life is incredibly commune like at times. I’m shocked the old boss wasn’t also the town mayor or had the sheriff in his pocket. Sigh.

          Reply
          1. Zuzu

            Well my boss was actually once suspected of (but not convicted of) murder. So there’s that! A friend and I once considered writing a graphic novel about it!

            Reply
        1. Bea

          This was a weaker Voldemort. Like if he lost his balls and was living under a stump. Which is funny since I know that skeeze may very well be foreclosed on. So yeah.

          Reply
          1. Julia

            I’m kind of questioning the whereabouts of original Voldy’s balls already, so maybe you mean he lost his horcruxes?

            Reply
  50. AnotherAlison

    Of course, if it works out, the OP and the daughter have an exciting opportunity to someday swap jobs.

    Reply
  51. Elizabeth West

    My gut instinct is to say no, don’t date at work and especially not the boss’s kid! Although I wouldn’t do it, I know people who’ve done so successfully. I think a few rules are in order.

    –You say you love your job, but you need to make sure you’re okay with potentially leaving. Dating at work has risks to both your job and your relationship. It can be hard to work with an SO, because you never get a break from each other. If you have a bad breakup, one of you may end up leaving and I’m betting it won’t be her. If company policy says no dating coworkers, you could get fired.

    –Have a plan in place in case the relationship fails. Will you be able to work with her (if you’re in the same area) or deal with not seeing her but knowing she’s there if she’s in another department? Can you transfer if necessary or would you have to leave? Think of it like an emotional prenup–nobody wants to admit a love might not last but you can’t live in denial either, especially when it involves your livelihood.

    –Create clear boundaries between work and home. I’d err on the side of complete professionalism–you both should act like you’re nothing more than colleagues. People will gossip. You don’t want the entire office involved in your relationship, even if they all know about it. They shouldn’t have to see it anyway.
    And off the clock, if you want to discuss work stuff, put a time limit on it–maybe talk about it for a half hour and then you’re done.

    Good luck, whatever you decide.

    Reply
    1. WCF

      I agree with the advice to create clear boundaries between work and home. When I was in a relationship with a coworker we decided not to tell anyone at work unless it got serious (like moving-in together serious). This ended up being SUCH a good decision. We eventually broke up, and I think that process would have been a million times worse with nosy coworkers gossiping and wanting details, plus constantly having to correct people who weren’t in the loop and thought we were still together.

      However, when your boss is your partner’s father it removes that work/life boundary by default. You no longer have the option to keep it separate. All the more reason to advise OP against this.

      Reply
      1. Tricksy Hobbit

        I agree. My parents met at work but didn’t tell ANY about it until they were engaged. Dad chickened out and called in sick on the day they were going to announce it. Mom still relishes telling the office busybody who kept trying to set her up with guys. (Heaven forbid a woman in her 30’s not be married!)
        Since it’s unrealistic to keep it from her dad for a long time, at least try to keep it under wraps from the majority of your coworker, bc it could look like favoritism.

        Reply
        1. Elizabeth West

          Yeah, especially if the relationship gets serious and you get a promotion: “Oh, Harry only got that job because of his girlfriend.” Even if that wasn’t the case, it could cause problems.

          Reply
  52. Hey Karma, Over here.

    You are not saying, “This is a great job and I have a long term plan here to do X and Y in my career. I like the area, the commute, etc.” You are saying, “I’m overwhelmed at the thought of looking for a new job because I’ve been here so long.”
    Maybe this woman is the start of a new chapter. Maybe not.
    You are thinking of long term relationships, of career changes and don’t sound really excited about it. Are you?

    Reply
  53. animaniactoo

    I think you need more information.

    1st: Talk to her about your concerns about dating her given that she’s a) a coworker, and b) the boss’s daughter. Explore how you would make it work. Do you give her father a head’s up now? When it looks like it might last past a month? How will you handle it if it doesn’t work out? Will you favor cutting the cord early given that it could get really messy in the office if it gets worse, or stick it out and trust each other to be adults? Will you make a point of not eating together too often? Be able to be professional and not too friendly/intimate/close in the office? Do you think you’ll be able to leave an argument out of the office and be professional and get work done as usual? See how you feel about her responses. Based on what you know about her, do you believe her? If you’re still interested at that point…

    2: Start looking at the job market around you and figure out how/where you could jump to if this all becomes a mess.

    If a new job would be easier to come by then a new girlfriend AND you feel comfortable with how you guys will be in the office and out of it… then sure, take the shot. However, if after you run down the options, you’re feeling pretty shaky about being able to find another job that would be as good and fulfilling as the one you have… start exploring ways to get yourself out there and run across more people so you have some more possibilities on the dating side.

    Reply
    1. JJ

      Yes, this, I just commented also about actually talking to HER, which seems to be left out of a lot of the advice!

      Reply
      1. Zillah

        Ehhh, it makes sense to want to make some decisions before talking to her. I don’t think anyone is suggesting that she doesn’t get a say, but OP should have some things sorted out in their head first. (Including whether this is a good idea at all! If it isn’t, there’s no point in having the conversation.)

        Reply
        1. animaniactoo

          But some of the info about whether it’s a good idea at all hinges on information that he can only get from her: Is she willing to be very casual and just testing the waters to begin with? How does she feel about the questions in my above post?

          How does he feel about those things is something he should think about, but also be open to modification based on what she thinks/wants if possible and if not – then it’s just a no go, it would be nice, but it would just make work life too awkward, ty.

          Reply
  54. Roscoe

    Are you a gambler? Because this is definitely high risk/high reward. So if you are risk averse, I’d say do it. There is a good chance that you will sooner or later need to leave this job either way. Best case, you and her get married, and its probably not good to have your father in law managing you. Worst case, you have a horrible break up and he hates you.

    Reply
  55. JJ

    I think people I generally way too defined by their jobs in America (assuming that’s where you are). You have 5+ years at this place, you WILL find another great job if you need to. Quitting is always much scarier before it actually happens.

    Why aren’t we talking about talking to the potential girlfriend?

    Be SUPER communicative with her about it. Like, “Hey I would love to take you out, but this coworker thing is a bit of a pickle, don’t you think?” and then ASK HER WHAT SHE THINKS. She probably has the same fears as you, if I was in your shoes I’d do 3 dates or so and see if there’s a real spark there (with a mutual plan to check in often and the agreement that either or both might agree it’s too risky). If it’s a go, make an agreement on what to do at work if you break up or have a fight, agree about how you’ll treat each other at work, agree how and when you’ll approach dad/HR as needed, together.

    Reply
  56. Lou

    Don’t do it. This has so much potential to be messy.

    If I’m honest, I kind of feel that if you’d liked her a lot, you would’ve accepted her the first time as well. It sucks being single but yearning after a relationship doesn’t often lead to good ends, and I’m getting that impression from your letter.

    Reply
  57. Emily S.

    Dating her would be unwise. IMHO, if you want to stay in this job, do not entangle yourself with her in any kind of romantic way.

    Personally, I have had only bad experiences in the past with dating coworkers. I made the mistake several times, and always regretted it, though luckily (in my case) the damage was minimal, since they were mostly superficial/casual relationships, and jobs that didn’t matter much (this was years ago — I’ve always tried to learn from my mistakes).

    Reply
  58. Storie

    There are a hundred ways this could go south. And maybe one way it works out.

    Finding myself in the Life Is Short camp. Harder to find a soulmate than a job.

    Proceed with caution!

    Reply
  59. Triple Anon

    It’s all a matter of priorities, but if LW dates the co-worker, they can never use that boss as a reference. Even if the relationship is great and everyone gets along, the reference would still be biased because it’s personal / family-ish, and therefore can’t be used professionally. So LW should have a good backup plan – new job prospects and alternate references – before dating the boss’s daughter.

    Reply
    1. Triple Anon

      Another thing. Ideally the new job prospects should be a step up – something LW would be really happy about – to prevent adding baggage to the relationship (“I sacrificed my job for you!” coming up during disagreements for years).

      Reply
  60. Elena

    Sounds like a high-risk venture. I think some things to consider:

    0) Are you two are of comparable attractiveness?
    1) Are you gallant, confident, have good manners, and otherwise give no reason for a woman to be ashamed to be seen in public with you?
    2) Do uou and she both KNOW that you won’t be butthurt or make it weird if shs says no?
    3) Does she have any known major problems you would be rescuing her from, like past substance abuse or
    major mental illness?
    4) Does she evidence dislike or mistrust of men as a class?

    Good luck!

    Reply
      1. JLCBL

        o_O
        Sounds like an alien trying to mimic earth human matefinding metrics. Definitely not addressing the OP’s dilemma, with the possible exception of 2.

        Reply
      1. I Wrote This in the Bathroom

        You are a stronger person than I am, my brain locked up on number 1 and I never really got past this to 3 or 4.

        Reply
  61. Dana

    If you have a real intuition that she might be The One (and you’re in fact searching for a The One), I’d date her, so long as you’re not prone to having such intuitions about every attractive woman of the body type and hair color you most favor. ;-) Finding a spouse who’s a good fit for you, assuming you *want* that, is more important than any job.

    But if you could probably find someone an equally good fit for you if you just put in the effort to go internet dating regularly, then maybe it’s not worth the risk.

    Reply
  62. Audrey Puffins

    If she were a co-worker OR the boss’s daughter, I’d say it’d be worth a careful shot. But she’s BOTH. Too risky, unless you’re truly willing and able to change jobs should it be a complete disaster or the romance of the century.

    Reply
  63. Breadwinner Mom

    I think this entirely depends on what your intentions are, what her intentions are, and whether you see this lasting for the long haul or just being an awkward fling.

    I started dating my husband under a similarly inauspicious set of social circumstances (he was close friends with an ex, all three of us are involved in the same intense and career-adjacent hobby that might as well be work), and it worked out against all odds. But the reason for this, as far as I see it, was that we were two adults who knew what we wanted. Those goals were entirely compatible, we fell in love, and the rest fell into place for the most part. On the other hand, neither of us is good friends with that ex of mine anymore and there have been awkward moments where that is concerned.

    So I’d say that if you’re not only pretty sure that you’re crazy about her and are looking for something that would probably last beyond your tenure in that position, and that she feels the same, and that you both have the kinds of personalities that can negotiate any fallout, go for it. If you just think she’s pretty and would be fun to date for a while, I would leave it alone.

    Reply
  64. Catwoman

    My knee-jerk reaction is that you shouldn’t pursue this, but if you really like her then you can at least talk to her about it and tell her about your continued interest as well as your concerns. You’re both adults, and whether or not you end up dating her is not entirely your decision (as you know). Something else to consider is how this might look to your coworkers. Will they accuse you of getting special treatment from the boss?

    If you’re worried about meeting other prospects, join Tinder or another online dating site/app. Do some volunteering. Get involved in community sports. Take an art class. Join an organization. Put yourself out there. Even if you don’t feel confident at first, this will help you to build confidence and meet more people.

    Reply
  65. IL Jim P

    There are always potential pitfalls in any relationship and in any job. Go on a date and see if it’s real before worrying about any of the stuff with the boss. That’ll take care of itself one way or the other. For sure tell her your concerns, I bet she’d want to know about it and discuss it too.

    Reply
  66. Frankie

    I mean, the first conversation you need to have is with her, asking whether she is 1) still single and 2) still interested in you. It depends on how the first round went, but not everyone would jump to date someone who’d rejected them not that long ago.

    Then you need to talk to her about your concerns and see what she thinks.

    If this does end up working out, I’d take it really slow to start with and assume you’ve just got a few dates lined up–don’t think of her as your de facto girlfriend. You guys would need to figure out if you’re really compatible before making it real and bringing that into work.

    I also would assume there will be consequences at work, one major one being that you might have to leave at some point. Are you willing to do that? Would you expect her to?

    And with dad as your boss it could just get weird and messy, even if your relationship is smooth sailing. Only you can decide whether that’s worth it to you.

    You could also be idealizing her because she’s around every day and you don’t have your own current romance. Is she a good option for you based on compatibility PLUS this work context that might make it difficult?

    Reply
  67. Former Govt Contractor

    I would say go for it if you had very strong feelings for her, but that’s not what it sounds like to me. When she asked you out, you didn’t immediately quit seeing your then girlfriend for a chance to be with her, which I think you would have done if your attraction to her was very strong. You sound more like, she’s nice, we have a lot in common, maybe no one else will come along… That’s not worth the risk in my opinion.

    Reply
  68. Anon for this

    Lots have already commented on the ‘recluse’ piece of your letter. There may be no connection here, but it also jumped out at me that you have been in this job and without a relationship for the same amount of time. Anything worth examining there!

    Good luck, whatever you decide. kb’s ‘questions to ask yourself’ near the top was particularly on point, hope you consider them.

    Reply
  69. HMM

    My 2 cents – you don’t have to go to dating immediately! Get to know her more, suss out her feelings (who knows if she still likes you), then if it comes time where you both believe it’s serious enough to move forward with, then you can consider if you should leave her job (maybe SHE wants to leave her job?), who to tell, how to manage the relationship at work, etc.

    This is assuming that both you and she are rational and can comport yourselves professionally any number of the ways this can go, but I imagine this scenario has happened before with both successful and not successful outcomes. Only you can decide what’s worth it!

    Reply
  70. Oxford Coma

    I would need to know the personality of a potential partner before I could figure out if I was willing to work with them, which is a bit of a catch-22 since you might not be able to get that information without dating.

    My company’s family tree is basically a knot–you see the same last names over and over. Still, I personally could not work with my spouse. The dude never shuts up, and he’s a major social butterfly with a BIG personality. It would not be long until I stopped being “Oxford Coma” and became “Cambridge Coma’s wife, who also works here”.

    Reply
  71. Tea, please

    From what I could tell from the letter, when she was turned down after first expressing interest, there wasn’t any fall-out at work. I think this shows that she can be a level-headed person who can keep a working environment professional even when personal is mixed in. But I think this is the info you need before moving forward. Can YOU keep it professional if you are upset in your personal life? Can you keep it professional if she turns you down this time? Can she? If you are so in love and so happy, can you hold it in at work? If you decide to go for it, I’d have a conversation early on about how to handle your relationship at work.
    I’m about to work at the same organization as my husband. We’ve set some very strict boundaries for our interactions at work–no touching even if we are by ourselves, no pet names. His co-workers are aware of the connection, so we’re not going to hide that. I’m in a role where I could provide feedback (not supervising, more coaching) to him, but my colleague will do that.

    Reply
  72. Someone Like Me

    There’s no clear yes or no here, but animaniactoo and JJ have the right idea in their comments above: TALK TO HER.

    I would probably go with something like this, delivered in person, of course:

    Hey…would you still be interested in getting a drink or dinner (or whatever) sometime? I think it would be really fun, but I have to admit, I am a little nervous, because I really love my job here and it can get complicated when you mix work with romance. But if you’re up for getting together and we can talk a little bit about how to navigate that, I would really enjoy getting to know you more.

    You don’t even need to mention that she’s your boss’s daughter. If she’s worth dating, she will understand that that’s one of your big worries. (If she doesn’t get why that could be problematic for you, or is uncomfortable talking about how you two would work together if this romance goes nowhere, then she isn’t a good match for reasons beyond being your boss’s daughter.)

    If you sense that she might get pissed and retaliate if you two go on a few dates and you decided you’re not interested, then I would not ask her out at all. But plenty of people are capable of handling a situation like this professionally.

    Reply
    1. Someone Like Me

      And of course: Ask yourself how you’ll handle it if she breaks things off. In fact, assuming you’re a man, I’d focus on that question a lot. We dudes have an unfortunate history of being real ass-munches when we’re rejected. If you think a breakup could result in you yelling at her, deluging her with calls or texts, or exhibiting passive-aggressive asshole behavior at work, spare her and yourself the trouble, please.

      Reply
  73. alison

    “I’m a recluse who hasn’t had a real girlfriend in five years”

    This can’t be your reason for dating the boss’ daughter. This can’t be your reason for dating anyone. “What if nothing better comes along” is almost never a good reason to do anything. If anything, it’s an excuse to justify a risky decision. I’m not saying the decision is unjustifiable, but that isn’t it.

    Reply
  74. Chatterby

    Talk to her about it.
    Mention your increased interest, but reluctance to approach the subject again because she’s the boss’s daughter, which might cause __, __, and __ issues if you do start a relationship.
    She might not be interested back, in which case this whole thing is moot.
    Or she’ll be interested and you can open a discussion on how to mitigate potential fallout, agreeing not to start anything if you can’t come up with a suitable plan.
    It would start a good precedence of working together to solve relationship problems, and being proactive about pitfalls.

    Reply
  75. Mallory

    How old is the boss’s daughter? Are we talking someone that is in their 20s? Or someone in their mid 40s or older? Does she have kids (ie boss’s grandkids)?

    Some of the “dad” dynamics really differ with age.

    Reply
  76. Delta Delta

    I’m joining the ranks of commenters who say no. If you get a different job and you still like her and want to ask her out, then maybe. I get it that it’s hard to meet people (romantically and otherwise) once you’re an adult and not in school anymore. However, since we all spend big chunks of our lives at work, it seems like we ought not invite problems where they don’t need to be. This feels like inviting problems.

    Also, what if you go out for coffee with her and it turns out you and she don’t click? Then you’ve got potential weirdness.

    Reply
  77. YarnOwl

    I think you have to decide whether dating her is worth potentially going through the worst case scenario (which, in my mind, would be things ending very badly between the two of you, you having to leave your job, her dad refusing to be a good reference for you or even going out of his way to sabotage you because of how things ended with her daughter, and your career somehow being impacted. Dramatic, I know, but we are talking worst-case here).

    For me, I really love my job and I want to stay here long term. I love my job enough that I wouldn’t date someone who has the potential to make me want/have to lose my job unless I felt like I would regret not taking a chance with that person more than I would regret losing my job because of them (and for the record, there are some people I work with who I would risk that for! But you have to decide if she’s one of them).

    Reply
  78. MicroManagered

    I think it’s really important what kind of organization you work for… If it’s a larger organization with policies in place for stuff like this and you have options like reporting to someone else, then this could work. If it’s a smaller family-run business where they’re likely to fire you on a whim? Maybe not a great idea if you don’t want to put your job at risk.

    Also, is your boss THE boss? Or is he one of like 5 managers who report up a few levels?

    Reply
  79. Akcipitrokulo

    It might be a time to take it slowly… see what happens. If it does go well, at some point you may want to consider looking for another job… possibly… it depends on how things work out.

    But it’s up to you. Personally, I think I’d want to explore it without burning bridges. And then keep in mind what I want… bear in mind that may change… and always be honest with her about what’s happening.

    Reply
  80. Oscar Madisoy

    Here’s another scenario that should be considered. (I haven’t read all of the responses, so this may have already been addressed by someone else.)

    In this scenario, the OP does date the boss’ daughter. They wind up liking each other a lot, and they fall in love. The boss has no objections. The OP and the boss daughter get married. In the context of being a married couple, they live happily ever after.

    Meanwhile…

    OP still works at the company. So does the boss’ daughter. The boss is still the boss (that is, he hasn’t left or gotten fired or been transferred or anything like that).

    There might be a perception around the office that OP gets special treatment or favors from the boss because the boss’ daughter is also Mrs. OP. The perception affects how OP is treated by his co-workers, and may or may not affect his ability to do his job.

    This is something the OP is going to have to think about as he considers whether or not to pursue a relationship with the boss’ daughter.

    Reply
  81. Noah

    noooooooooooooooooooooooooooooooooooooooooooooooooooooooooooo [quick breath] 0000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000!

    Reply
  82. Boss's daughter

    I’m the boss’s daughter. Met a guy who works for my dad. Dated and fell in love with the guy. Married the guy and celebrated our 17th anniversary this year. It can totally work. Communicate, set boundaries and make sure to at least partially separate work and home.

    It can definitely work.

    Reply
  83. HeightsHeifer

    I would not get caught up in a relationship with your boss’s daughter unless you are ready to find another job. Relationships with a coworker are one thing, and one I tend to warn others against, if there is not a power play involved and everyone can behave as adults, then it’s not the biggest deal. But in this situation, you have to worry about your girlfriend’s dad being your boss and that is soooo messy.

    I would maybe test the waters and make sure you are both on the same page first. If you’re both ready to take that leap then you need to do some job searching.

    Reply
  84. OlympiasEpiriot

    I have no idea what you should do.

    What I do:
    I have my Exclusion C-C-C Zone. If you are or can be a Client, Contractor or Colleague, you could be Will Yun Lee, Clark Gable, Frank Grillo, Billy Dee Williams, and Daniel Craig all rolled into one and I won’t touch you. I am not in academia, but I would consider a student a “client” if I were a professor and a “contractor” if I were a student. I especially stay away from anything related to Bosses.

    This has not prevented me from dating.

    I also do not believe in there-is-only-one-special-person. There may not be enough of a dating pool where I am at a given time, but, I let it slide. Things always change.

    Also, about your situation: Last year she was interested. Her taste may have changed since, she may have gotten to know more about you and decided that she likes you but not LIKES you like that, or she might have a crush on someone who is not you right now. Just because you are interested now doesn’t mean she’ll reciprocate if you tell her you’ve changed your mind.

    Reply
    1. Wrench Turner

      Never heard the CCC rule put so clearly – I like it! Going to have to remember that one.

      Reply
  85. Llama Grooming Coordinator

    LW, you’re probably an awesome person and you deserve love. But I think dating your boss’s daughter, especially in this situation, is a TERRIBLE idea.

    At least right now. I’m saying this for two reasons:

    1) You really like your job. To quote your own words, you “love it more than most anything.”

    2) I apologize for being rude, but you seem to be eager to find a relationship. Which is fine, but this is an extremely high risk scenario.

    In the best case for you two, you live happily ever after. At that point, you’re basically part of your boss’s family, which makes your job really complicated – everything that happens at work is suspect. (And if word gets out if you two are dating, this almost certainly happens as long as you’re dating.)

    In the most likely scenario, things end and you become your boss’s daughter’s ex. And that’s an entirely different set of issues – even if things are amicable, you’re still his daughter’s ex. That’s going to be at least slightly awkward all around.

    And God forbid things go terribly (if you do date her, I hope they don’t!).

    That’s not to say you shouldn’t ever date her! She sounds lovely. But right now it sounds like you really love your job more than you love her, and I don’t want you to potentially ruin that, LW. If you guys ever go out, I hope it’s after you find another awesome job (don’t go find a job just to date her).

    Reply
  86. That Would Be a Good Band Name

    I feel like this has all the makings of a great romantic comedy. I love romantic comedies, so I really want to say go for it. But things always blow up in the middle of those. I can’t really see a way that all of this works out with you keeping this job and dating this person long term. In the movie version that I’m creating in my own head there would be a spectacular falling out at work but the happy ending would include you getting a job you love even more than this one.

    I do think you could quietly go on a few dates, but be prepared that if things are going to be long term that you’ll probably need another job.

    Reply
  87. Anonny

    +1

    My main concern is how your boss will handle the situation. Even if it’s the ideal perfect relationship, fights are inevitable, and depending on how close your coworker and boss are, she may share those details with him, which could in turn affect his treatment and opinion of you. You have to consider that YOUR BOSS will also gain a new insight into you as a person (and vice versa), and if he doesn’t like what he sees, or how you act in the context of a relationship with his daughter, that could spell trouble for you professionally

    Reply
  88. Radams528

    Nopenopenopenopenopenopenope back far, far away. There is so much crud (to put it mildly) that can go wrong in situations like this.

    Reply
  89. MLB

    Whether you do or don’t date her depends on many different things.
    1. Is she a co-worker in the sense that you work for the same company only, or do you work on the same team/together on certain projects. If you work together at all, this could be tricky and awkward if it doesn’t work out. And if there’s potential for either of you to become the other’s supervisor, are you willing to leave for another job if you’re dating?
    2. If you do start dating, it doesn’t work out, and she paints you as the bad guy, do you think your boss would start treating you differently because he feels you betrayed his daughter?
    3. Can you honestly say if things didn’t work out that you could be mature enough to still be civil and professional to her at work (and hope that she can as well)?
    4. You said something that concerns me about not having a GF in 5 years. Do not use this as a reason to ask her out. I went the majority of my life being single, and didn’t meet my husband until I was 40. But before I met him, I was perfectly content to spend my life single. There’s nothing wrong with being single, so please don’t use this reasoning to ask her out because it will most likely end in disaster.

    I have friends that met at work and stayed together for the long haul, but your manager being her dad makes things a bit more complicated. I lean more towards no, but if you decide to go for it, you need to be prepared to start looking for another job if things get crazy. So what is more important to you – your current job or a potential relationship?

    Reply
  90. sfigato

    I just want to add that true love is harder to find than a job you like, so if you think this woman might be the one, or you’d at least be in a long-term relationship AND you are ok with having to find a new job potentially, go for it. Just proceed with caution.

    If she’s nice and cute and might be fun for a laugh but nothing serious, go look elsewhere.

    Reply
  91. Anonforthis

    You mentioned that you’re a recluse who hasn’t had a girlfriend in a really long time. I’m sure she’s great, but is she maybe one of the only single, close-to-your-age women you’re seeing regularly? Maybe that’s where it’s coming from.

    Reply
  92. Crystal

    Only if you are prepared mentally and financially to not have a job and if you’re ready for the drama/stress that would come along with doing this. That being said good luck, life is short and finding people you genuinely like is tough.

    Reply
  93. Keyboard Cowboy

    Absolutely depends on whether you believe you’re mature enough to keep these two parts of your life completely separate, including if the relationship ends, and if you believe your boss and your boss’s daughter can do the same. If everybody is able to be entirely mature (unlikely! but I don’t know what your age range is like) then it may be OK, although it could potentially turn into conflict of interest and you’d still need to move.

    Reply
  94. DontSendYourKidstoHudsonUniversity

    A few years ago I met my boss’s stepson at my boss’s wedding. We really hit it if off and my boss joked that her spouse wanted to set us up because we were perfect for each other (her spouse told our office manager of grand plans to set us up etc.) I didn’t think much of it until boss’s stepson sent me a facebook message and invited me to have coffee or brunch or something along those lines. I wasn’t sure how to handle it, but was interested and accepted. We had a nice time and under other circumstances probably would have gone out for a more datelike date. I couldn’t get over how this would affect my office dymanics (whether it worked out or not) and ultimately was very direct in saying I had a great time, I’d love to be friends, but you’re a member of my boss’s family, so that’s really all I am interested in. It wasn’t terribly awkward. The fact of the coffee date is, however, something I have NEVER openly acknowledged to my boss. I assume she knows it happened, but I’m very glad I didn’t pursue it.

    Reply
  95. Wrench Turner

    “Don’t dip your pen in the company ink” was a phrase a teacher taught me a long time ago and I stick by it. Don’t date anyone you work with, period, unless you’re actively job searching and you’ve already got a foot out the door.

    Reply
  96. Harriet2

    I was the daughter in a situation just like this – DO NOT DO IT. It has taken THREE YEARS to get past the bulk of the fallout, and that’s with me being incredibly professional 99% of the time (I had one really bad day and just went home after a particularly hurtful comment). It’s been damaging to the team. It’s been damaging for reputations. There is just so much you don’t know about each other until you’ve been dating and it can go spectacularly wrong.

    If you are desperate to date this person, I’d honestly consider finding a job elsewhere before giving it a try. If you don’t want to do that because you like your job, find a different person to date. There are lots of people. LOTS. Try a different one.

    Reply
  97. Mammal

    Do you know that she’s even still interested in you? If you turned her down last year, there’s a good chance that she lost interest after the first rejection.

    Even if she’s still single and still interested: no. You work with her AND she’s your boss’s daughter. Multipling negatives only produces positives mathematically.

    Reply
  98. TheHamsterGirl

    As someone who is currently in a workplace relationship at a job I love I can relate.

    My advice is to sit down with this woman and have a frank and honest conversation with her. Discuss what might happen if you pursue it, what might happen if you realize it wasn’t meant to be, think long and hard about how you each handle disagreements, disappointment, frustration etc.

    My partner and I had many conversations about our mutual attraction that frequently came to the conclusion that pursuing a romantic relationship would be a bad idea given our working relationship. After several of these conversations we decided to pursue a romantic relationship anyway, but it was very intensely thought out, planned and discussed. For the first few months we kept it quiet to test the waters and then once we were sure we wanted to proceed publicly we took that step.

    The key is to be very very honest with yourself about what you can and can’t handle, and how you deal with difficult situations. In my case we decided to pursue it because, not to be too cheesy, we realized that there was something between us that we had never experienced before and to paraphrase Jim Halpert, I think even then I kind of knew that he would be my husband.

    Reply
    1. AlsoDatingCoworker

      This thread got unusually judgy of people who date coworkers pretty quick! I’m in a very similar boat as you… We talked a lot BEFOREHAND about how a relationship would work, how we would keep things professional at work (including when we do work together), how we’d handle things if it doesn’t work out, etc. We talked about what our boundaries would be during work (no parking lot kisses if one of us drops the other one off, stuff like that) and made sure we were in agreement. We also talked about how far that would go… would we deny a direct question about whether we’re together? Would we have lunch together? Would we take one car or two when we’ve spent the previous night together? I think communication is key–both on the front-end and on an ongoing basis.

      We are still in the “keeping it quiet” phase (6 months) and not even 100% sure we’ll ever go public at all (our positions do not fall under our company’s policy that requires us to disclose). At work, it’s actually pretty easy to act like we’re not dating at all. I think part of it is that our relationship built very slowly over about 8 months before we were “official” and in that time we built up a lot of mutual respect. We’re both mature adults, so there’s no reason to expect that would change if we decided not to be together anymore. But, like you said, we realized we both had strong feelings we’d never felt before. We felt we owed it to ourselves to explore them, but that doesn’t mean one of us has to give up the career we’ve worked hard for!

      It’s totally possible to date a coworker and handle it maturely.

      Reply
      1. TheHamsterGirl

        YES! Like I totally get the initial “bad idea” reaction, but the fact of the matter is, every situation is different.
        My partner and I have been together officially for over 2.5 years (living together for almost 2) and honestly it’s been the best decision I ever made. The relationship itself is wonderful and our coworkers are very supportive (honestly I’d be more concerned about how some of my office friends would handle it if we broke up than how my partner and I would haha).

        Good luck to you and your office love! Wishing you many years of happiness. :)

        Reply
  99. Good, Cheap, or Soon. Pick Two.

    Okay, you’re a recluse; as a die hard introvert, I can relate. That being said, there are solutions. Websites like metope offer a chance to join small, casual groups like book clubs, movie clubs, or just get together and play Cards Against Humanity. There are online dating sites if you’re lonely (figure out what you want in a relationship, research which one best suits your needs, and there are actually plenty of resources on how to build your profile and send messages). If you don’t like the idea of involving the online world in your social life, consider getting a dog and going to the dog park regularly. You’ll find a community that’s easy to join and you know you’ve got at least one thing in common with everybody there.

    What do all of these things have in common? They don’t complicate your professional life. You do not even know if this woman is interested. You have not had a significant romantic relationship in five years. It has been over a year since the initial interest was mentioned and you told her that you were pursuing someone else. That’s three strikes. Beyond that, you’re playing ball in a minefield. You’ve got a job you love at a company you’ve been with for half a decade. You get along great with your boss. Don’t blow that up by suddenly changing the dynamic. Even if you do not get into a relationship, even if you do not go on a single date, expressing your interest will change that dynamic. You will be the man who asked his daughter out on a date.

    Reply
  100. bonkerballs

    I like to think of myself as both a romantic and a pragmatist. So I say go for it, but go for it with your eyes open. Be aware of what could happen if things go poorly. Be aware of what could happen if things go really, really well. Be *prepared* for those things. And I would make sure, if/when you do begin a relationship with this woman, that you hash this out with her pretty early on. Make sure she is also aware of the challenges and consequences that could go along with this relationship, that you’re both actively thinking this through and are both willing to wade into this. This does not have to be a mess.

    Reply
  101. SometimesALurker

    There are already 315 comments so forgive me if I am repeating something already said upthread, but it sounds like work is one of the big things that makes you happy right now. (Many folks would envy you that!) Some people, not necessarily you, are prone to making the person they are dating The Main Good Thing In My Life (which can sometimes put unhealthy pressure on the relationship, but that’s out of the scope here). If the two of you date, she becomes the Main Good Thing, and later you break up and decide you need out of this job where you’re coworkers, you might lose two really big things at once. That could happen even if she’ isn’t the Main Good Thing, but might be less devastating. So, for your own sake and for the sake of not accidentally pinning all your wellbeing on your relationship with her, I’d recommend seeking out something that can be your “other good thing.” Join a club or a casual sports team or music group, something that can contribute to your sense of self and your support network if things get rough. It may take a few tries to find that “other good thing” that works for you, but it’s worth it.

    Reply
  102. TreePeople

    I’m just kind of amazed here at the number of people who don’t think adults can act like adults in the workplace. Is it just me?

    If there is someone you’re interested in dating, but the situation makes it complex, you discuss it. You set ground rules and expectations. You don’t take it too quickly, or invest too deeply, until you’re certain. And if despite your best efforts and intentions, it doesn’t work out, you behave like grown-ups and keep it out of the workplace.

    And yeah, I get it that the person being the boss’s child is an extra layer of complexity, but can we not trust the boss to behave like an adult too? Can we not expect the woman to communicate to her parent in an adult way and her boundaries to be respected?

    Why are we expecting bad behavior from either the boss or the parties in the relationship if it doesn’t work out? When did theatrical breakups become the norm?

    LW, for what it’s worth, in my workplace there have been three office relationships. Two resulted in marriage and one in a civil breakup, with people who continued to work together.

    Reply
    1. AlsoDatingCoworker

      Yes! This thread is weirdly judgy of people dating coworkers and I’m surprised! (And full disclosure: I’m dating a coworker, so I am probably more invested in the topic.)

      I am dating a coworker and that’s exactly what we did… We took it very slowly and have had many and ongoing conversations about what the boundaries would be. Obviously nobody approaches a relationship thinking it will end, but we did talk about that too. We are mature, intelligent adults who had a longstanding mutual respect for each other… why would that change if a relationship didn’t work out?

      For those of us who need to work for a living (most of us, that is) we spend a LOT of time at work. Why is it so egregious that we might meet a romantic partner there? If there’s not a conflict of interest (such as a direct-report relationship), then why should one of them have to make a drastic change to their career before even *finding out* if there’s a match? That’s SILLY. It’s very easy to tell a LW to quit his job or not fall in love when you’re just commenting on a blog. I don’t think that’s particularly plausible or helpful though.

      Reply
    2. Detective Amy Santiago

      Probably because we read this blog on the regular and see many firsthand examples of adults not acting like adults in the workplace.

      Reply
  103. Harper the Other One

    I think that dating a boss’/supervisor’s daughter is a different scenario than another coworker, and even that can get pretty messy. OP, I think I would consider if there’s a way that anyone else can supervise you before you begin exploring dating. If the relationship goes well, you don’t want accusations of favoritism, and if it goes poorly, you don’t want your supervisor’s assessments to be affected by personal feelings.

    If there really isn’t anyone else who can supervise you (or at least be responsible for reviewing your performance) then I’d be very leery. It’s going to be very hard to keep personal and professional separate in this situation and while the possibility of a relationship is obviously of interest to you, this is a job you love and there’s a lot of potential to lose a sure thing for a maybe. If you really want to pursue this relationship and there’s absolutely no way that you can make those boundaries more clear, personally, I would seek another position (and a good one, not a “good enough” one) before I went ahead.

    Reply
  104. MissDissplaced

    Maybe.
    It’s not ideal. First, you’re coworkers, and that’s just generally not a great idea in the best of circumstances. Second, it’s your boss’s daughter and that’s fraught with other problems.

    But what’s that to stand in the way of true love? If you can both me mature adults, it may work! But if this is the case, you should prepare to leave this job or at least work at a different division.

    Reply
  105. Lady Phoenix

    Nope. She is not only your boss’s daughter but also your coworker. Dating her would deatroy all sense of workplace/personal boundaries.

    If she was one or the other, then fine. But both? That is a big NOPE for me.

    Reply
  106. Lady Phoenix

    I read this again… andwer is still no:
    1) The whole coworker+boss daughter mix
    2) The fact you only seem into her because she had a passing interest in you and that you really want a “girlfriend”, ie: a girl who has a set role as you life partner. Forcing someone into this little box can be stressful enough—especially if it just because she is a girl.

    She may have moved on, so having ancoworker cone up and demand her to be his “girlfriend” can set off potential skeeve bells.

    I would instead focus on developing connections UNRELATED to work. Try meetup, online dating, special events, etc. Don’t force your work life to be your whole liffe.

    Reply
  107. Going anonymouse for this one

    Heh. Personal experience over here. I think it depends on how reasonable the *dad* is and what kind of relationship father/daughter have. Health boundaries, no helicoptering etc.

    My coworker and I (boss’s daughter) dated for a couple years. It did not end well and as far as I know he still works there. It was not an ugly split but not super amicable either but my dad did not retaliate.

    I left the company shortly before the end for another job so that might have factored as well.

    So I’m not going to say no right off the bat because that relationship was a fantastic life/professional learning experience for me. But just make sure you really think about all the different ways it could go sideways.

    Either way, best of luck!

    Reply
  108. A commenter

    Hard pass unless you’re prepared to lose the job when you two break up.

    If that’s the case, go for it.

    Reply
  109. bohtie

    Regardless of whether she’s the boss’s kid or not, this part stuck out to me: ” It’s not as though I feel confident in just moving on to the next opportunity because I honestly don’t know where that could possibly be.”

    It sucks being lonely, but being lonely and lacking other romantic prospects is not a good reason to start a relationship with someone. Especially if you’ve already rejected her before, she’s probably filed you away in the “Not An Option” category, so consider that you might be dealing with “dating the boss’s daughter” OR “I tried to romance the boss’s daughter and it did not work,” both of which are potentially really awkward.

    Also, this is a really stressful, socially nuanced situation you’d be putting yourself into, which is something to consider for a self-described recluse — no matter how careful you try to be, you’re going to have to spend a lot of time explaining yourself to other people and dealing with their judgment, and that may not be your jam. (I say this as a fairly intense introvert and general shy person: the thought of navigating the complicated waters of a work relationship, period, let alone one with these kinds of dynamics, sounds absolutely terrifying and that alone would be enough for me to back off.)

    I’m not saying no, but if you were to pursue it, you’d need to be, in my opinion, two seemingly contradictory things: 1. really upfront with her (like, make sure you find out whether she’s actually still interested), and 2. willing to take it really slow and let things go the way they go. If you just show up one day and announce that the boss’s daughter is your girlfriend, it’s gonna be a lot more chaotic. (I’m not doing a good job explaining this, but basically, it’ll be easier on everyone involved if it’s obvious that you’re taking your time.)

    Reply
  110. Hokius

    My dad dated the boss’ daughter when he was a young man and she became my mom. It can work out. I’d still be really hesitant about it…

    Reply
  111. writelhd

    I weigh in on the side of…hang out with her, get to know her, but move slow, and reassess how you feel often along the way. Start by hanging out as friends and being frank and open about your concerns but also your willingness to try it slowly–in other words communicate like a mature adult and see if she can do the same. Not everyone can do that, but some people can and it’s not fair to assume you won’t be able to. It can be possible that you’ll be able to figure out for yourself as you go on and get to know her better which is more important: the job, the chance at a relationship with HER in particular, or even trying to keep both and accepting the (potentially very) awkward social territory that comes with having that–because that too is a possible outcome. If it doesn’t work and you break up, yeah, that *can* be bad, but breakups can also be things mature adults are capable of moving past, even into positive working relationships. Every single relationship is different on that score. And I’ve even seen spouse couples work at work. Sure, it is often fraught, may not be allowed everywhere and certainly requires leveling up in your relationship management skills on a lot of different fronts–but it’s not like it never ever happens. Either way, what you’re doing is stepping outside of what is safe, and into something that is unknown, and from that comes possible good and bad consequences but also the opportunity to learn more about how to manage relationships of all kinds–romantic and work.

    Reply
  112. So much Lisa

    I would do it. But keep in mind you’ll probably have to find another job sooner or later. It’s super possible she is mature and awesome and won’t involve her parent unnecessarily and you guys will continue to work together without issue after a breakup. It’s also possible you’ll live happily ever after and realize that, for the sake of your relationship, you need to work apart. I’ve lived the latter. We loved working together but eventually had nothing to talk about but work (and because we were both *AT* work we had nothing to talk about when we got home because… we were both there). Now we work apart and have been together for 10 years, 2 kids.

    So unless your job is the dream, and you want to be a recluse (not totally clear from your letter), I say take a chance on love. If you think it’s the real deal, and I think you do.

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  113. staceyizme

    I don’t think that you should date your boss’ daughter. You’re setting up a paradigm with a lot of potential for problems. There are a lot of great people out there and you’ve already dated some other good candidates, even if those relationships didn’t last until the present day. You should strive to excel in your career and keep your focus on your professional goals there. You should also strive to excel in your relationships and keep a mindful focus on your personal goals there. But the two should not be conflated. There is too much overlap for everyone involved and it’s not going to end well if it ends. Why do that to yourself when the whole problem is preventable? You can always consider dating her later, when you are working elsewhere (and if you’re both still available and interested). I know that there are a lot of stories about people who broke the rules or recommendations and everything turned out fine. Thinking about it by the numbers, however, those stories are the exception and the reality is more likely to be an awkward attempt to clean up your personal mess in a professional setting if one or both of you decide to stop seeing one another after some time of dating.

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  114. Married a Coworker

    I agree with everyone who suggests taking it slowly. There are so many risks inherent in dating a coworker, I don’t think it should ever be the result of a whim. Unless you really think the relationship could go the distance, I would advise against it. Not wanting to be lonely, thinking it would be exciting, etc aren’t reasons that will hold up, so you should take time to really make sure there is a good foundation there. OP, I could be way off here, but I sense that you are more excited at the prospect of a relationship, than convinced that she is the partner you truly want. And in that case, the potential (probable? Inevitable?) HR nightmare far outweighs the potential benefits of the relationship. Obviously dating for fun is okay, but work is not the place for starting casual relationships. IMHO, there are MUCH better places for that.

    But I also think it’s silly to say that it can’t ever work (assuming you can avoid an ethical mess). I love that my relationship with my husband started at work. It gave us a lot of great opportunities to get to know each others’ character. The spark was always there, but we spent months building a strong friendship. I finally asked him out one evening and he turned me down (he had a strict no-coworkers policy). As much as I owed it the company as an employee, it was the importance of his friendship and my respect for him that made it easy to keep work drama-free. He later told me he had a similar experience. We were even better friends after that, and before long, he was ready to make me the exception to his no-coworkers rule. Everybody’s story is different, but my ultimate point is that your office romance will have the best outcome if you are patient and are confident that it’s truly about each other, and not because it sounds exciting as an idea.

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  115. SL

    This is a bad idea. Do not date or attempt to date your boss’s daughter. You will become miserable at work if you do this no matter the outcome. Love is hard to find but a job your actually enjoy is harder.

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  116. Girl friday

    For yes/no questions it would be really great to have a poll feature- as it boils down to many well-worded answers to a yes/no question.

    Reply
  117. Caitidid

    Hi OP, I’m a little late to the game, but this question really spoke to me. As a high functioning introvert, I get where you are coming from. Getting yourself out and interacting with new groups is hard, and online date makes you ill just thinking about it if you’re anything like me. So, you’ve met this girl and it’s exactly how you hoped this might work, you meet her in a less social, therefore less stressful, setting. You connect, get along well, and the relationship (peer/coworker/friend) grows naturally. The timing is finally right, and you know she was interested, at least at one point recently, and you think you think you’re ready to take the plunge. And then come to a screeching halt when you remember it’s not just a coworker, it’s your bosses daughter.

    Ok, not great, but not hopeless. If you were someone more outgoing with no problems meeting people, I’d say move on. But you’re not, you’re a recluse/introvert, which just means that finding a way to connect with people is *hard*.

    (All of you who say he needs to get out there more, I challenge that you have no idea what its like to try and connect with someone when you meet on a blind date or at a bar when social conventions just confuse you and your desperately trying not to puke all over this person during a panic attack while trying to figure out if your level of discomfort is worth the tenuous possible connection you made. And if it doesn’t go well? Goodluck getting up the energy/courage do that again before the end of this decade…)

    So, as a fellow introvert that feels like they understand this situation as something that could be possibly great, but also terrifying, here are some suggestions.

    First, how are her and her dad’s relationship? If they are able to keep it professional in the office, hopefully, any drama will stay out of it. If they are very familial, that’s a flag that if something goes wrong, it might bleed over into work.

    I’ve seen your posts about your job, you love it and you’re good at it, so I assume you really don’t want to leave. Ok, but what about her? Is she here cause it’s the family business, or because it’s what she’s passionate about? These are things to know so you understand the landscape.

    Set your own boundaries. How fast are you willing to move? If you or her all in after a few dates, I love you by the second month, moving in by 6 months, is that ok with you? Also, nothing is wrong with this, but I would suggest that people who want to take things slower are probably safer office dating options overall because it’s often easier to end things with fewer entanglements. Just be sure you know what you want, and what lines you draw when it comes to work.

    A lot of this requires you to talk to her. Maybe things have changed on her end, maybe she has the same reservations, maybe she doesn’t think it’s a big deal. Where she stands, and if she understands some of your reservations, is big deal, and will tell you a lot. Because of this, I also suggest a “pre-date”. Go get coffee together and talk frankly and honestly, tell her your concerns, figure out where you guys stand, see if you have the same perspective on work and dating and what that would look like. Cause if you don’t, the relationship is not likely to work anyway.

    So go for it, not at full throttle, but at a steady, comfortable pace. Like a boat in a no wake zone, get through the first part at an easy pace, and once you have figured out if this is something you can make work, then hit the throttle.

    And from introvert to recluse, good luck. I hope it works, but if it doesn’t, that’s ok too. You’ll never know unless you try, but that doesn’t mean you have to be reckless. Be honest, communicate, and trust your instincts.

    Oh! P.S. If it does work, I would suggest that it be her job to set boundaries with her father, not you setting boundaries with your boss. You just need to keep it professional at work with him and her.

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  118. Lowermanagement

    I will say, yes, date the girl, as long as you are prepared to either find a new job or demonstrate great professionalism should something happen. Also, your boss and coworker/potential girlfriend should also be able to be professional as well should something go bad. I dated a coworker, and it ended and he in a crazy turn of events ended up being my boss months later but I think we had time to let emotions go and he was professional about it, as was I. It’s just a matter of whether or not you’re prepared to deal with the consequences should something go wrong. You also have to take into consideration what kind of relationship they have with each other. Is she going to tell him every time you do something stupid or something that upsets her? Is that going to inevitably strain professional and personal relationships?

    Reply

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