I want to ask my boyfriend’s manager to help me surprise him at work

A reader writes:

I’m in a long distance relationship. I live in New York, while my boyfriend of one year and a couple of months lives in Nevada.

I want to surprise him next year in March 2016 for his birthday with a surprise visit to his job. He’s a great employee, never late, and rarely takes a sick day unless he’s seriously sick. I thought to ask his manager if I could maybe wait within the office and ask that he’s called in and would see me in there? Or maybe go in as a customer for the ride he operates and surprise him. Not sure.

Is there any particular way I should go about asking? Or should I just wait till he gets off work to surprise him after? 

Well, you wrote to a stick-in-the-mud, but wait until he gets off work.

I mean, it’s not the worst idea in the world, but since there’s no reason you can’t pull off the same thing outside of work, that’s a better option.

While some managers (and some boyfriends) would be perfectly fine with this plan, others might not be. Here’s why:

* You have no way of knowing details about his work life that could make it a bad idea. To give one example, what if he’s already on thin ice (or will be by next March) with his boss for having too many personal distractions at work? In that case, this would be last thing he or his manager would want. And you can’t really know that kind of thing from the outside.

* Many managers would feel uncomfortable saying yes to your request because they don’t actually know anything about you. Maybe you’re an ex who your boyfriend has been trying to shake. Maybe you’re a stalker. Who knows. The point is that the manager doesn’t know, and if she’s smart will realize that she doesn’t know.

* Lots of people don’t want surprise social visitors showing up at their work at all, no matter how much they like the people themselves. Maybe he’s having a busy and harried day and is going to feel pressure to stop what he’s doing and talk with you. Maybe he’s covering for someone else and juggling two sets of responsibilities. Maybe he’s the middle of dealing with a demanding customer. Who knows.

Or, maybe none of this is the case and he will be thrilled and to see you, and his manager will be delighted to help you arrange it.

But why not just leave work out of it? After all, you can still surprise him — just don’t do it at his workplace. And really, wouldn’t you rather surprise him with this when he can fully focus on you anyway?

{ 256 comments… read them below }

  1. UKAnon*

    I think you need to ask why you want to do it at his work OP. Is there a particular reason, or just seeing him as soon as is possible? ‘Cause if it’s the latter, you’re really not going to get to see him in any meaningful sense (conversation will be out because he’ll have to get back to work, and I assume that even if you were so inclined his office doesn’t approve of quacking on the work sofa) and this plan is fraught with difficulties. If you wanted to check with his manager whether he’s able to leave on time that day so you can book a restaurant table or something, I think that falls into more of a grey area where it’s understandable and some managers (most?) won’t mind, but turning up pushes it into a bit too much without a really good reason to do so.

    1. Katie the Fed*

      Honestly, I would find a significant other showing up at my work to surprise me with no warning offputting and slightly controlling. This is my space. He has his. I don’t need/want him in my space.

      1. KarenT*

        Agreed. It’s very intrusive, even from someone who knows you really well. OP, why not call one of his friends and arrange surprise drinks.

        I also think the manager would be weirded out by the early request (March 2016!). I say this as a fellow extreme planner: even if you decide to go ahead with the request, it’s way to early.

      2. Kelly O*

        Mr. O is working two part time jobs right now. I even feel weird stopping at the grocery store when I know he will be there, and I called ahead to make sure it was okay to say hello at his pizza delivery job when my daughter and I came back from a few days away.

        It’s just impolite to me. I realize I’m old-fashioned, but I think that sort of thing works best for perhaps being there when he gets off work or something.

      3. Heather*

        It brings to mind the episode on Friends when Ross kept showing up at Rachel’s work place and he couldn’t understand why she wasn’t thrilled with it.

  2. Kelly L.*

    I’m going to be a bigger stick in the mud and recommend against surprising him at all, unless you really know he likes that kind of thing. I’ve had a couple of LDRs and in one of them, the guy did come surprise me once. I literally stepped off the bus to find him waiting at my stop. It ended up being kind of a pain for all sorts of reasons, mostly just because I’d already planned the next few days and hadn’t planned a boyfriend visit into them. At least drop Strong Hints so he knows you’re up to something, or at least that’s what I’d suggest. Or maybe that’s just me.

    1. AnotherFed*

      Good point – what if they’re off on travel or something else? Most people can turn down or reschedule a trip if they know they need to, but if it’s a surprise visit they don’t have a chance!

    2. JMegan*

      No, I was going to say exactly the same thing. I would find this kind of surprise really disconcerting, especially if I had plans that I now had to either cancel or include him where I wouldn’t have otherwise. Even if my plans were an evening alone in front of the tv – actually, especially if my plans were an evening alone in front of the tv, because that’s often the hardest thing to schedule!

      And not to scare you off even further, but I actually had a boyfriend break up with me after I pulled a surprise like this. We weren’t long distance, but I did show up at a place and time where he wasn’t expecting me, and he did not like it. At all. And it was only after the fact, that I realized how much I would not have liked it either! Maybe not to the extent of breaking up with a person, but the TL;DR is certainly that not everyone would be comfortable with a surprise like this.

      OP, I think you’re better off asking him directly “Would you like me to surprise you with a visit one day?” I agree that it takes away some of the point of the surprise, but on the other hand at least you know how it’s likely to be received. And the specific date can still be a surprise, once you have his permission. Good luck!

      1. Allison*

        Totally agree. As much as I may have fantasized about a long distance lover showing up at my apartment one evening, the fact is that I haaaaaate having last minute stuff sprung on me, and having to rearrange my schedule and change my mindset to accommodate it – I’ll do it for someone I really like, but it’s not ideal. Not to mention, there’s a 95% chance my room would be a mess and I wouldn’t have any good food in the kitchen!

        If a guy wanted to come visit me, I’d some heads-up so I can keep my schedule clear, clean up my apartment, plan some yummy meals, and think of places for us to go while he’s in town.

        1. Kelly L.*

          Yes! I could just see myself having the place a wreck, and being broke and figuring on eating some of my “lean times specialties” (I have several boring but filling meals I can whip up when money is short), and having picked up an extra shift of work or something, and bam! boyfriend appears and I’m like “Welp. Make yourself at home. I have ramen and cheese…”

      2. RO*

        Too much of a surprise. My friend surprised her boyfriend (NY – AZ) and that was the weekend they broke-up.

      3. Sadsack*

        I agree with your suggestion about asking if he would like a surprise visit at all. Now would be a good time since it is do far in advance that he’ll likely have forgotten all about it when the time finally comes. But I still would not do it at work. He is a ride operator, so it would have to be timed when there is no one else waiting to get on the ride. Plus, for the other good reasons that others have mentioned.

    3. The IT Manager*

      I’m not spontaneous. I would hate this. Besides wouldn’t it be more fun to tell your BF you’re coming so he has the anticipation and can make plans to do things with you. It’s his birthday; he’s likely going to have plans with friends which you can join but perhaps both you and he would prefer a quiet birthday celebration alone which he can arrange for if he knows about your visit. Plus what if skips work that day to hang out with friends he doesn’t tell you because he doesn’t expect you.

      Ignoring my own non-spontaneous nature, it sounds like if you surprise him at work them you’re stuck hanging out with him while he finished work which can be awkward and unprofessional. He operates a ride so it doesn’t sound like an office, but still he probably has to focus on getting customers strapped in safely and stuff so a visiting GF sounds like an unnecessary distraction.

      1. Meg Murry*

        Yes – given that it’s his birthday it is likely he will have plans for the night or the weekend that you are just inviting yourself to. Or given that you mention he’s in NV, it’s possible his friends will have arranged a totally not girlfriend appropriate event in Vegas.

        If you know his friends, you might be able to have them help you with the surprise by making plans that you are (secretly) part of – like making reservations for dinner and including you in the count.

        But I would leave work out of it – or at most, arrive at his office 15 minutes before the end of his shift to surprise him.

        Plus, not to be cynical, but it’s July and his birthday is in March. I know you’ve already been in the relationship for a year, but a lot can happen in the next 9 months. You could break up, one or both of you could quit your job or move to a new city or any multitude of other things. I don’t know whether you are just mulling this over at this point or actually in the planning stages, but I’d slow way down if I were you.

        At most, if you really want to surprise him, could you plan a visit for Saturday but actually show up Friday as a surprise? When I was in a LDR, looking forward to visits from my SO and planning them months in advance were one of the things that kept us going – so I feel like you would be cheating him out of some of the fun and anticipation of visit planning by surprising him.

      2. TootsNYC*

        Oh, I forgot it was his birthday! He may well make plans, if he thinks you won’t be around! Not fair, then.

    4. Lily in NYC*

      And there’s always the chance he’s not as invested in the relationship and is seeing other people – god forbid he’s dating a coworker and OP shows up. Yikes.

      1. Applesauced*

        Yeah, but how great would that AAM letter be? “Dear Alison, this crazy lady showed up at the office claiming she’s my boyfriends girlfriend…”

      2. Uyulala*

        The relationship cynic in me thought that might be why the OP wanted it to be a surprise and at work.

        1. some1*

          I don’t think you are being cynical. Showing up at your significant other’s work, univited, definitely gives off a territorial vibe. “I want your coworkers to know you have a GF and that it’s me.”

          1. Andrea*

            I actually trust him, it’s not being territorial or anything. In many ways, from interests to ideals: he’s a male version of me lol

            I also trust that if he did do anything (like cheat) that karma will pay him a visit.

            But the visit would be my gift to him for his birthday because we don’t see each other often. Once a year if we only see each other for his week vacation.

            If we did nothing but just spend time together after his day of work in the hotel, I’m 100% content with it :)

            1. some1*

              Sorry, I should have written can definitely give off that vibe, even when that’s not the intention.

              1. Andrea*

                It’s fine ^_^ I’m talking to him about it now. He said he’d be all for it and I would have him meet me at the hotel lobby after work.

                Probably have balloons and Panda Express delivered if possible. His favorite take out.

                1. YaH*

                  See? You were awesome to talk to him about it, and it sounds like you have a nice idea of how to celebrate with him, and now you know he’s going to be eagerly anticipating your arrival. :)

            2. TrainerGirl*

              You only see each other once a year? Then it’s probably not the best idea to just show up for a visit. Everyone doesn’t love surprises even if there’s nothing going on. Your first two statements (“he’s a male version of me” and “if he did do anything (like cheat) that karma would pay him a visit” makes me wonder what your motives are for this visit, and especially for wanting to surprise him at work. Even if you two are a lot alike, he may not think the exact same way. Just because you might love for him to show up and surprise you at work doesn’t mean that he will.

    5. KT*

      This. I had a long-distance boyfriend do this, and I’m sure it seemed super romantic…but my grandmom was int he hospital and my family and I were all taking shifts to be with her, and boyfriend arrived when it was my turn to be at the hospital.

      Sorry boyfriend, my commitment to my ill grandmother came first.

      There’s so many reasons why a visit like this would be inconvenient (without even the surprise at work factor!)…he could be on thin ice at work, he could be facing a mountain of work and needs to put in 15 hour days, he may have family commitments, or he may have a flag football tournament.

    6. Saucy Minx*

      Mr Knightley’s observation suits me: “I don’t approve of surprises. The pleasure is never enhanced and the inconvenience is considerable.”

    7. Ad Astra*

      That’s a good point. Not everyone likes surprises, especially when those surprises are planning to stay at your house and interrupt the plans you’ve made for several days.

      If the OP knows how to reach this boyfriend’s roommate or other close friends in the area to get an idea of his plans and routine, she might have more success. For instance, they could make a bunch of plans with the boyfriend that weekend (to prevent him from scheduling an invasive medical procedure or out-of-town trip or whatever) and then “hand over” their allotted time to the girlfriend.

      But, even with accomplices, it’s a good idea to really think about whether this guy is someone who appreciates surprises (and the accompanying disruption to his routine).

    8. BRR*

      I would need them to surprise me at the exact right time. When I had no plans and my place was clean.

      1. virago*

        This reminds me of my parents’ reaction when my sister and I held a surprise party to celebrate their 25th wedding anniversary.

        Dad walks in, looks around, sees a lot of people, smiles broadly, grabs a beer and starts talking to the nearest person.

        Mom walks in, looks around, sees a lot of people, looks abashed, heads over to me and whispers, “You should have told me people were coming over! I would have done some cleaning!”

      2. Meg Murry*

        Oh yes. I would NOT want anyone to surprise me with showing up and expecting me to put them up at my place! I would be so embarrassed to bring my SO back to a place that very definitely needed cleaning and the many many piles of laundry dealt with.

    9. HB*

      I don’t love surprises either. I argue that anticipation is part of the enjoyment of something (you know, that time leading up to the big trip when you are all excited).

      1. TootsNYC*

        That’s why people doing the surprising think it’s such a great idea–they get TONS of anticipation! All of it, in fact.

    10. eee*

      ehh, it all comes down to knowing your audience. I was in a LDR and my boyfriend successfully surprised me with a visit–it worked because it was just the weekend (he showed up Friday afternoon, leaving Sunday morning), he checked with my mom (who I lived with) to see if it was a) okay with her, b) see if I had plans that weekend, and he also had friends who lived in the area who he could spend time with if I was unexpectedly busy. Also, a few years previously, when I was in college and he lived an hour away, he had planned on surprise visiting me for my birthday, and wound up getting unexpectedly sick. He told me that he had been planning on surprising me, and I was super enthusiastic about the idea. I would also add that in both cases, the surprise was because he found out at the last minute that he was going to be able to visit me–for my house he decided to tag along for the first leg of a road trip his sister was taking.

      So, if you’re gonna surprise your long-distance SO:
      1. figure out whether they would like a surprise visit in general (if they seem against the idea, DO NOT PROCEED)
      2. try as best you can to schedule it for a time where you know they won’t be busy
      3. keep it a short visit
      4. Be prepared to entertain/house yourself if something unexpected arises

      1. Elizabeth West*

        This. My ex-bf (I’ll call him Atticus) surprised me when he was driving out to the state he had been assigned to by his new job. He had told me he planned to take a more southerly route, and I said I wished he could drive through here so we could see each other. He texted me about three pm that day asking what time I got off work and told me he was getting off the road to get something to eat, etc. I assumed he wanted to know so we could get on Messenger later.

        It was about a quarter to five, and I was sitting at the front desk wishing I could see him, and I heard the outside lobby door open. I could see someone enter (we had an outside door into a foyer and then French doors into the office). I thought, “Wow, that person coming in looks an awful lot like Atticus—HOLY CRAP!”

        Yep, it was him. :)

        We had a lovely visit and then the next morning he got back on the road again. He planned that well because:

        –He knew I wanted to see him (because I had told him).
        –It was close to the end of the day, so no worries about him hanging around for a few minutes.
        –If my boss was weird about it, we could have arranged for him to take my key and go on to the house, so it wasn’t like he needed a ride or anything.

        *sigh* Too bad he wasn’t someone I ended up staying with!

    11. Shan*


      I started dating a guy in college and when Winter Break came along, we both went home to our own families, who lived about three hours apart from each other. Boyfriend said he wouldn’t be able to visit me over the break because he had to work, but since I’d been thinking about breaking up with him, it really came as a relief! When I got home, my family asked me about Boyfriend, and I casually told them I was going to break up with him. The *very next day* he showed up at my door at 8 am – he had planned to surprise me with my family’s help! It was incredibly awkward for me and my family. I stuck it out and broke up with him after that, but I don’t think my family will ever help a boyfriend surprise me again – and that’s fine with me!

    12. nep*

      Not just you. I would not be at all pleased with a surprise from my long-distance partner.
      I reckon the OP knows that this person would be OK and even happy with it. To each his/her own.
      (Agree with Alison and others, though, if OP does go ahead with it — why do it during his workday?)

    13. Emily K*

      Yes – this happened to me once! There were no issues at all with our relationship, but my boyfriend showed up a day early for a regular weekend and I have to say that I hated it, and I felt incredibly guilty for hating it. I was quite looking forward to my plans to make a bunch of mac and cheese, smoke some, and binge-watch Netflix…and instead I had to transition into hosting-my-boyfriend mode. And of course I felt so guilty for wishing my boyfriend, who I only got to see a couple times a month, hadn’t done this nice thing of surprising me and feeling guilty that I was such an unappreciative girlfriend…but honestly I just don’t like unexpected socialization with anyone, no matter how much I love them.

    14. The Bookworm*

      I’m another person who agrees with Kelly L. Your surprise visit may bomb.

      It isn’t work related, but when I was in college, my out of state boyfriend came for a surprise weekend visit. It was AWFUL. I had 3 major tests to study for & I felt pressured to spend time with him instead of studying.

      I wasn’t happy to see him (I was already stressed about my tests before he showed up), and he was upset that he’d gone to so much trouble to see me & I wasn’t happy about it.

    15. Melissa*

      Thiiiis. I actually like surprises, but I’ve been in an LDR too and I actually specifically told my then-boyfriend to stop trying to surprise me. The logistics of planning it are so elaborate but then you cannot plan for the other side’s reaction or schedule, and my then-boyfriend (now husband) would actually get kind of upset if his surprise didn’t work out the way he wanted it to – which was frequently, because I’m not planning for him to be there and have planned my day accordingly. Then you have to scramble to rearrange your schedule, which may introduce more work into it.

  3. LBK*

    I think it’s a particularly bad idea since it sounds like he does customer-facing work, which doesn’t lend itself to pausing to socialize. At most he’ll probably just be able to say hi before he has to go back to work, which leaves you sitting around waiting for his shift to end anyway.

    1. Tomato Frog*

      I love seeing people I know when I’m doing customer-facing work. But they always stop by with the understanding that I won’t be able to stop what I’m doing. I think it’s a lovely idea for her to buy a ticket to his ride, say “surprise,” and then say she’ll see him when he gets off work. Bad idea to do anything that involves his boss or him stopping his work.

      1. LBK*

        Ah, see that’s totally different from my experience. When I was in retail people would always want me to stop and chat and it was kind of like…thanks for visiting but I have other stuff I need to do.

      2. Dana*

        When I was in retail I liked when people I knew stopped up, but only if they were actually gonna buy something (even just a pop or candy bar) and then I could talk to them during the transaction, stand and chat if I was slow, or shoo them along if someone else came up. As long as I could keep the counter between us I didn’t feel unprofessional. To me, stepping around the counter to talk for extended periods of time (okay in retail that was like 10 minutes, but still) was something I silently judged my coworkers for doing.

      3. Cath in Canada*

        I worked as a bartender one summer and I loved it when friends popped in for a drink while I was working. But that’s way, way different to strapping people into a roller coaster or whatever, where you really need to focus and there’s a constant stream of people. No-one dies if you pull a Guinness too quickly…

  4. AnotherFed*

    I would hate this if anyone did it to me. It’s quite likely that I wouldn’t be at my desk and would have specific tasks that HAD to get done before people left for the day, so any visitor for me would be stuck hanging out with the receptionist for up to several hours before I could pull away. Even if it were my manager, he wouldn’t pull me out of customer meetings for this (nor should he), or be able to babysit so the visitor didn’t have to wait in the lobby (with no chairs).

    1. Ivy*

      I had my manager surprise me once with a visit from husband and kids during lunch on my birthday. What she didn’t know was that I was having an unexpected call with clients just scheduled over lunch time, so I had just time for a very quick bite with colleagues then husband and kids showed up, I had a minute to say “hi and bye” to them and left them to take lunch with my colleagues (almost all of which are young people without kids). Awkward!

    2. themmases*

      I would also hate if someone did this to me. There are hosting duties involved in having someone come to your workplace: show them your office, find them someplace appropriate to wait, find something entertaining or meaningful for them to do that doesn’t involve sensitive information, possibly introduce them to people who are busy themselves. It’s a pain even when you see it coming. I’d hate to have it sprung on me.

      I would also just find it undermining for a partner to contact my boss for any reason other than an emergency. I have a friendly relationship with my boss, but the only reasons I can think of that my boss should meet my partner, in order of acceptability to me, are: coincidence, holiday party, my boss and I are very good friends, my partner comes to my office for some reason that had better be good. Just coming for a social reason risks making the boyfriend look like he doesn’t understand work boundaries, without giving him an opportunity to opt out of this plan.

    3. MashaKasha*

      Ooohhhh I suddenly remembered that a guy I dated very briefly, very very long ago, did surprise me at work. I was a counselor at a summer camp. I was well liked by the campers, but not so much by the camp director. I’d been a camper there myself and she felt I wasn’t strict enough with the kids, not enforcing the rules and regulations and the schedule strictly enough etc. Mind you, this was a math camp for nerdy kids ages 13 to 16. For many of these kids, it was the one month out of the year when they could hang with people like themselves and be accepted and liked for who they were. So yeah, I let them enjoy that one month out of the year more than the camp director would’ve liked me to. I turned a blind eye on a lot of things. Anyway, right before leaving for camp I’d met this guy and we went on maybe three dates. I was 20 and he was 18. Absolutely nothing serious. One day, I’m running around camp working my ass off and all of a sudden he shows up. It was very awkward and inconvenient. I had to do work. My work day did not end until something like ten or eleven PM and it was still early afternoon. He wanted attention and I couldn’t give him any. He wanted to make out and we quickly found out that the camp director was very much opposed to any making out on camp territory. We’d find one empty room after another, hide there, close the door, and she’d barge in on us five minutes later and chase us out of there. Finally I gave up and told him “thanks for coming, but there isn’t much I can do for you right now, I’m on the job and am expected to be working.” and added “you’d probably feel the same if I showed up at your work”. He left, upset, and I never saw him again. (Probably a good thing.)

  5. Former Diet Coke Addict*

    I’m sure your boyfriend is a stand-up guy, but there’s the possibility that he believes himself to be a good employee but his boss has a different opinion. I would always rather err on the side of caution when dealing with someone else’s employment–and even more so when a surprise girlfriend visit might send the message of “not serious” or “another distraction.”

    Plan something fun to surprise him when he gets off work. More fun and less hassle.

  6. MicheleNYC*

    I agree with Allison on this one. It is really awkward and uncomfortable for the manager. I was put in this position when I was a young manager and really felt like I couldn’t say no. I had an ex-employees fiance ask if she could take the day off so they could go get married at city hall. I wanted to say no so badly but really felt like it wasn’t an option. The main reason I wanted to say no was that I knew she was marrying someone that was physically abusive. She had to be sent home on her 2nd day on the job because he had hit her so hard he ruptured her ear drum. I tried to talk her out of it but she had her mind set.

  7. Interviewer*

    Is no one noticing that she is planning a surprise for March 2016? That’s over 8 months from now.

      1. some1*

        They might not even still be together, or he might not still be working there, or have the same manager, or living there….so many things could change by then it might be moot point.

        1. De (Germany)*

          Well, she probably needs to buy plane tickets well in advance, so I’m not seeing why she shouldn’t already be planning it. I don’t think the question came up because she wants to contact his manager *now*, just asking what to do in the future…

          1. some1*

            If he lives in Vegas you can get cheap airfare pretty much all the time from every major US city.

          2. eee*

            my issue for this would be–if you’re planning it that far ahead in the future, why not *make sure* the person will be available for that date? How obnoxious (for everyone!) would it be if you’ve had a weekend scheduled as a surprise visit for 8 months, and three days before she shows up her boyfriend buys concert tickets to use that evening. Or trades shifts with a co-worker and has to work that evening (if he is operating a ride, I assume that might be shift work). Or decides that’s the weekend he’s going to get his apartment fumigated, or agrees to help a friend move, or any other host of things that he wouldn’t do if he knew she was visiting. For myself, when I was in a long distance relationship, I was very happy the one time he surprise visited me, but that was because it was spur of the moment (he made the decision the day before) and was able to check my current availability (which was completely free). Last weekend, I bought tickets to the ballet for me and one other friend Friday night, scheduled a movie outing with a group of friends on Saturday, painted part of the house on Saturday, and decided to leave work early on Friday and finish a big work project over Sunday. If my boyfriend decided to come visit me that weekend, and I found out he had been planning this since last December, I would be very annoyed, because I would be unable to change many of my plans. Why not just schedule it so that I could keep the weekend open?

          3. Melissa*

            Yeah, but not 8 months in advance. 2 months is fine; even 4 months would be understandable, but I think 8 months of planning is a bit much.

      2. Tanith*

        Give Interviewer a break on the semantics…(s)he was just remarking that it seems quite early to be planning this or asking the boss about the boyfriend’s availability,

          1. De (Germany)*

            Especially an issue so obvious that it would be strange for noone to have remarked on it yet… I was honestly confused and asking for clarification.

    1. Erin*

      Silly question. Why is that weird? They’ve already been together over a year, it’s not a new relationship. No reason to think they won’t still be together in eight months. Also, she’s probably taking the time to save up money for the trip, it might be the best time for her to take off work, etc., etc., etc.

      1. Kelly L.*

        I knew my current relationship was getting serious (several years ago) when he told me he’d gotten us–not “him,” “us”–a room for an event that was like 6 months away. It was a cool moment, realizing we were both pretty darn sure we’d still be together then.

        1. some1*

          What was that old Margaret Cho line? How much it sucks to realize you want to break up with your boyfriend, but then you remember that you have concert tickets?

        2. Oryx*

          Yes. My boyfriend did something like this similar, made a comment about us going to some event six months down the road and in my head I was all “Oh, okay, so you see us still together six months down the road, too. Great!”

      2. MsM*

        I still don’t see why you’d need to even worry about involving the boss this far out. They probably don’t know the work schedule or if there are going to be issues around that particular date yet. And they might forget that it’s happening and assign the boyfriend to something important that day or forget that it’s a surprise and blab.

        Of course, I’m with the people who think this is not a good surprise to pull in the first place, so maybe I’m not the right person to ask.

        1. MashaKasha*

          Most surprises are not good to pull in the first place. I still have a vivid memory of my then husband bolting from his surprise 40th party with a terrified look on his face. This one does seem especially not good, because it involves surprising a person in the middle of their workday, which is IMO never a good idea.

        2. Emily*

          I agree on all counts, but will allow that the LW is just making plans for making plans at this stage. Better to be considering the pros and cons of this scenario now, including asking for AAM’s advice, than to write to Alison at the last minute and wind up pulling the trigger before she gets to answer the letter!

      3. MashaKasha*

        Over a year is still a new relationship, especially when it’s that long-distance. Saying this as someone whose bf of two years, that we’d had future plans with, one day showed up to our weekly after-work get-together with a large bag full of my stuff from his apartment and informed me he had to move on. That was two years ago and I saw him maybe three or four times since. I absolutely would not plan a surprise visit across country, book tickets, bring his manager into this etc. for something that’s eight months out, for a relationship like the one OP describes. Just like I don’t make any plans involving my current bf, also of a little over a year, without making sure I have a plan B in case we’re not together anymore by the time the planned event rolls around.

    2. Christy*

      I noticed it too, then I realized that yesterday I called a restaurant in a city I haven’t relocated to yet to see if the restaurant’s rental loft had an elevator for the hypothetical wedding with the girlfriend I haven’t decided to marry yet. Some of us are planners. (And yes, the restaurant has an elevator to the loft. I know you were concerned.)

      1. Persephone Mulberry*

        And this totally reminds me of the episode of Friends where Monica inquires about the wedding venue and Chandler hears the message and freaks out (because everything reminds me of an episode of Friends).

          1. some1*

            The original letter reminded me of Ross showing up at Rachel’s office with a picnic when she had to work late. When the show first aired I thought Ross was being sweet but now I totally get Rachel’s annoyance.

            1. kozinskey*

              On the other hand, there’s the episode of Gilmore Girls where Logan shows up with a surprise picnic and totally saves the day for Rory. So…only show up if you’re prepared to be useful?

              1. MsM*

                I think that’s the first time I’ve ever seen anyone give Logan props for being a good boyfriend.

                1. So Very Anonymous*

                  I’ve just been rewatching the last season of Gilmore Girls since it was originally on, and have been surprised that I hate Logan less than I did originally. But I still think his good boyfriend-ness is just a role he’s playing to get something he wants; he seems incapable of not working whatever situation he’s in. Agree that his willingness to actually help get the paper out (along with picnic) is a good thing, though.

            2. Ad Astra*

              Ross is the worst! His stupid, possessive antics could have really hurt Rachel’s career, especially considering she didn’t have much experience at that point and would likely be relying very heavily on the references and reputation she earned at Ralph Lauren.

              1. some1*

                Especially because Ross had canceled on her and the other friends when he had a work emergency!

              2. Ethyl*

                When Friends was finally up on Netflix, I spent like two weeks texting my media studies friend “I HATE ROSS SO MUCH” like, every ten minutes.

      2. De (Germany)*

        I’m not a big planner myself, but I know quite a a few people who plan their trips a year in advance or so.

        And yes, even early in a relationship – it just wouldn’t occur to me to not make plans for 9 months out in a long term relationship because we might be broken up by then…

      3. Allison*

        I’m a planner too, and to be honest, if I was gonna do something like this I too would want to plan a while in advance, but I often try to restrain myself from making any solid plans too far in advance. It could come across as overly eager, foolish, and creepy, and as I’ve learned in past relationships, things can always change. Sometimes it just takes one bad night to screw everything up . . .

    3. Sally-O*

      I was also surprised by this. If the boyfriend’s job is to operate a particular ride, that doesn’t seem like the type of job he will definitely still be in next March. Maybe he’ll have moved elsewhere in the company, or maybe he won’t even have the same boss in 8 months. It’s WAY too early to contact a boss about something like this – I am doubting the schedules for March 2016 are already set. (Although I don’t think she should contact the boss at all.)

    4. Lead, Follow or Get Outta the Way!*

      I did notice this and feel it’s a little premature not unless she is planning the ultimate proposal.

    5. Elsajeni*

      I mean, it’s certainly early to be planning at a level as detailed as “I’ll wait in the office and have the manager page him,” and way too early to contact the manager about it even if she decided that was a good idea. But it’s not crazy to be planning, in general terms, what you’ll do for someone’s next birthday starting as early as “right after their last birthday,” especially when it will involve long-distance travel. And I don’t know if this is part of what you’re getting at, but it seems weirdly cynical to me for the people in the relationship to be expected to make plans on the assumption that the relationship won’t last! I mean, of course they could break up, but anything could happen — as long as the OP wants the relationship to continue and doesn’t have any particular reason to believe it won’t, avoiding making future plans in case they break up is like avoiding making future plans in case she gets hit by a bus tomorrow.

  8. moss*

    Don’t do this. Your personal life has no place at your boyfriend’s work. There is no benefit at all to surprising him at work even if he’s perfectly happy to be surprised. At work. His coworkers will not think this is cute & fun, they’ll think it’s rude and a distraction and will forever think less of him.

    Surprise him at home if you must surprise him.

  9. TCO*

    I once contacted my then-boyfriend’s boss to help with a surprise. My boyfriend traveled a lot during the day, and I wanted to surprise him by meeting him at work at the end of the day (not during the workday, just at the end of it) to take him out to dinner. I checked with the boss to see if my boyfriend’s appointment schedule would have him at the office at the end of the day or not.

    One key distinction is that I knew this boss quite well–he and my boyfriend had been close friends for many years before working together (and no, that didn’t always work out well). We went to each other’s weddings, we hung out at each other’s houses, etc. I wouldn’t have done this under OP’s circumstances, where she wants to 1) meet her boyfriend during the work day, and 2) doesn’t seem to know her boyfriend’s boss very well, if at all.

  10. AndersonDarling*

    Hate to say it, but March 2016 is a LONG way away. You could be living together by then, he could have a different job, who knows.

    1. Laurel Gray*

      Or the total opposite – they could have broken up and no longer be in contact (sorry for the Deborah D. Downer scenario)

    2. Connie-Lynne*

      Or he could have a different boss! His boss might move positions or companies in that time.

  11. Academic Librarian*

    Before there is an avalanche of comments…just no. I don’t even think it matters if the manager says yes. I don’t think it matters if it a laid back culture. No. Ride? That means he is public facing. Still no. Schedule a fabulous time together. Get some tickets to a show. A spa day together at the Bellagio (sp?) a trip out to the national park. Work is work.
    No good can come of a surprise. I am sure there will be commenters who had lovely, fabulous, memorable surprises at work. The down side is way to great.

    1. Laurel Gray*

      Seconding this.

      You didn’t state what city in Nevada so I am not going to assume it is Vegas or Reno. However, you can get great deals (and even better well in advance) for getaways to both cities and I think it would be a good idea if you did this instead. I too have been in LDRs and there is something about a pop up surprise in a LDR that is very different than one when the person lives in the same city. When you and your beau are local, you have a better understanding of their schedule and routines but it isn’t the same with an LDR. I think the reaction to a surprise pop up of your local boyfriend to his job with a surprise like a lunch invitation is waaaaay different than one that involves packing bags and boarding a plane.

  12. Erin*

    Yeah, unless you know his manager personally (and it sounds like you don’t) I wouldn’t risk it. You just have no way of knowing the dynamic there, even if you were local.

    Side note though, love that you’re surprising him! Cute, awesome idea. I would reach out to one of his friends instead and have them help you arrange something. They can help you make sure you’re surprising him at an ideal time, and not when he might be swamped with work or personal things.

    1. Lily in NYC*

      Caveat: I hope OP knows if he’s the type who would appreciate a surprise and isn’t just doing it because it seems like a fun thing to do. Someone doing this to me would be my biggest nightmare come true (surprising me with a visit; not just showing up at my job).

      1. Erin*

        I assumed she knows her boyfriend well enough to make that judgement, but I hear you, that’s certainly worth considering. I have to admit I’d be pretty pissed though if I went to all this effort and he was like, “Yeah I don’t like surprises.”

        1. Mallory Janis Ian*

          Well, my husband and I had been married for about six years before he had the opportunity to learn that I hate pop-in surprise visits at work. So it is possible to know someone and to misjudge their possible reaction to a particular sort of surprise. I had appreciated all his other surprises that did not involve my place of employment.

          1. Erin*

            Fair point, but you’re married and presumably living together. This young lady lives across the country from her boyfriend and sees him once a year. Even if I hated surprises at work, if my boyfriend from another state showed up, my excitement at seeing him would trump any discomfort or annoyance at him basically invading my workspace.

        2. I don't like surprises!!*

          My boyfriend showed up at my job with all the accouterments for Valentines day one year…because he thought all women loved that sort of thing. I don’t think he’ll ever set foot at my job again. I HATE surprises and I just kinda stood around like a deer in headlights and probably looked like I wanted to jump out the window. My coworkers thought it was great and I felt awful for my reaction, but I was in shock.

          NO NO NO! Unless you specifically know your audience.

          1. Erin*

            Were you long distance, though? That is the key thing here most seem to be overlooking. OP stated in an above comment they see each other once a year.

            1. Mallory Janis Ian*

              I think even long distance, you run the risk of the surprisee not liking his workplace invaded.

      2. Cath in Canada*

        A friend of mine when I lived in Glasgow went home to Ireland unannounced one random weekend as a surprise for her Mum, and her Mum was so startled, she actually slapped my friend! Just a weird reflex to seeing her unexpectedly – she apparently apologized profusely and said she thought it was a ghost or something!

        OTOH a friend here in Vancouver recently went back to Scotland unannounced for her sister’s birthday party, and everyone shrieked and cried and loved it (the video’s super cute). Know your audience!

        1. Grouchy*

          I, for one, would not be happy about a prodigal sibling arriving and stealing star status at my birthday party.

      3. Windchime*

        Yeah, it would be a nightmare for me, too. I need to plan ahead when people are going to be in my space. I need to make sure the housework is done and that I have groceries, for instance. I’m find with beer and popcorn for dinner but that doesn’t suit everyone.

  13. Joie de Vivre*

    Please don’t. Not to be a Debbie Downer, but surprises don’t always work out the way we hope.

    I was in a LDR and my boyfriend showed up at work as a surprise. I was in the middle of something for a major customer and couldn’t drop everything to go spend time with him that afternoon. Security didn’t want to let him in (which made me actually worked for me because I hadn’t told anyone at work I was in a relationship and did not want to explain!!) so he wound up sitting in the lobby with a bunch of flowers for a couple of hours waiting for me.

    Unfortunately, I had pretty much decided to end the relationship, just hadn’t had the conversation yet. If only he had told me what he was planning, it would have saved us both a lot of aggravation.

  14. jhhj*

    If he works as a ride operator, then asking the boss — MUCH closer to the time — if he will be working at that ride at the end of the day so you can surprise him in line at the LAST MINUTE of his shift might work. But this is premature. See what feels right in February.

  15. Graciosa*

    Please – not at work.

    Alison’s second bullet point is a big deal. I don’t think I know enough about my employees’ private lives to make this kind of decision.

    No, I’m not an insensitive jerk, but I don’t ask these questions. So yes, when Jane announced her engagement to Fiance Frank, I congratulated her and knew that AT ONE TIME they were engaged.

    But if Frank calls me up and says he wants to surprise Jane – well, I don’t know that this isn’t because yesterday she discovered him running a child pornography ring in the living room while she was supposed to be at work and he needs an opportunity to pressure her not to turn him in to the police.

    And if this happened, it’s possible that she is not ready to talk about this at work – and may never be – which is fine, because this is work. The employee – not anyone the employee may have a relationship with – gets to decide how much personal information to reveal to others at work.

    And as I said, I don’t ask. It’s none of my business.

    But if you call me, you’re asking me to use my position AS A MANAGER to make a decision about an employee’s personal life.

    This is really inappropriate.

    I should not be deciding Jane will be happy to see Frank. Jane gets to decide that. My job is to stay out of it – at least until Jane comes to me and explains that she has a restraining order and I need to quietly make sure security keeps him off the property.

    OP, you who are in the relationship may be scoffing at all this because everything in your relationship is sunshine and roses. But I don’t know that. Don’t drag me into this.

    If everything is sunshine and roses, he’ll be at least as happy to see you *after* work – probably happier because you can do things together in privacy elsewhere that he is not free to do in the work environment and on the clock.

    1. Hlyssande*

      Yes! This ties into the grand romantic gesture narrative that gets murderous exes into workplaces and dorms because ‘they seemed like such a nice boy/girl and it’s such a sweet gesture that I’m happy to help!’

      Please don’t do this, OP. Like Graciosa said, the manager shouldn’t be put in the middle here. Sure, you’re a quality person, but they don’t know that. If they do this for you, the next person could be an ex getting back at their former partner.

      It seems sweet on the surface, but it really isn’t (even leaving out the interruption problem).

    2. Lunar*

      Yes! Not only is this important for reasons of safety, but I just don’t want my manager to know that much about my life and relationships and so I would be so uncomfortable if someone I was dating contacted my boss about something like that. I find it awkward and wouldn’t want to answer questions about it later.

    3. Dana*

      I think this is an important point to make because you’re putting all sorts of undue pressure on the manager/boss. It isn’t their job to check to make sure you aren’t a crazy stalker or ex-girlfriend. It isn’t their job to get involved in their employee’s social life and arrangements.

      And, of course, there’s the added element of being in a long-distance relationship–something that works out fantastically for some people and goes horribly wrong for others. Not to knock the OP’s situation, but I feel compelled to share: When my best friend was in college she dated a guy for over a year. He graduated the year before she did and moved back home (about an hour away). Her mom worked at a bank in his hometown and was socializing with a co-worker. Co-worker was talking about her daughter’s boyfriend of a couple months who was oh so sweet. His name was Mike. My best friend’s mom was like, oh, my daughter’s boyfriend’s name is Mike. Yeah, come to find out, it was the same Mike… My best friend thought she was dating a great guy. But distance does funny things to some people.

    4. Verde*

      +1000 – also why you don’t discuss anything with significant others re. benefits, pay, etc. Those conversations should only be with the employee, as you don’t know what all is going on in their private life.

  16. YandO*

    Also…March 2016 is a LONG time from now. My lovely BF and I have been together for 8+ years and I still would not do this to him because…..well, so much can go wrong in the next 8 months, even if not our relationship related. People relocate. People change jobs.

  17. Nope*

    Even if he is a stellar employee and your relationship is solid as a rock, I still think it’s a bad idea. The OP said he operates a ride, so I’m picturing her trying to squeeze in between a possible line of customers, distracting him while he’s trying to operate the ride, and waiting for the ride’s cycle to end to get all of 5 minutes with him. It doesn’t actually sound like a job where he could stop and talk. Even if he could talk, I know for me, I wouldn’t want to expose my co-workers or my customers to my mushy couple time. To me, that’s unprofessional. So, you have made all these plans just to get five minutes of putting him in a really bad position, where he most likely will not be able to express his feelings for you. I vote ‘no’.

  18. TootsNYC*

    I love anticipation, so I’m not a fan of surprises. A surprise like this means that *I* don’t get a week’s worth of “ooh, my sweetie is coming!” And that’s a fun I particularly enjoy.

    I also have come to believe that surprises like this are really a power trip. The surprise-er gets all the clout, all the control. The surprise-ee turns into a mere prop in their elaborate plan. It’s really all about how much the surprise-er will enjoy it; “look at me and the wonderful surprise I am planning.”

    I don’t admire these sorts of surprises anymore.

    Also: Glamour magazine recently did a story about surprises like this, and a lot of the stories were of the surprise-er finding out that the relationship was pretty much over.

    1. Former Diet Coke Addict*

      I loathe surprises like this, and the power thing is part of it. Like the gigantic stick in the mud I am, I also loathe surprise public marriage proposals and despise surprise military homecomings (especially for children–they can be really damaging and unsettling after the first flush of surprise).

      And while I’m complaining, I’ll share a story of a guy I knew whose girlfriend took a job in Dubai. She planned a week vacation in London, and the boyfriend planned a surprise trip to London to see her (from where we live in Canada–no small feat!). About a week before her trip she confessed that the trip to London was meant to see her new London boyfriend and she would no longer be dating the first guy. It was….let’s just say we had a very depressed guy on our hands for a few nights. Surprises do not always work out.

      1. JMegan*

        Yes. I’m firmly on Team Stick in the Mud for surprises like this, including surprise marriage proposals and surprise military homecomings. They put so much pressure on the surprise-ee to be happy about it all, regardless of how they really feel about it.

      2. The IT Manager*

        +1 to loathing public proposals and military homecomings.

        But for your second paragraph, I saw that coming in your story because why would someone fly from Dubai to vacation in London without her BF? If she had wanted to see him she would have flown all the way to see him or would have invited him to join her in London. Poor guy probably had hints galore and was trying to save the relationship. If you want to break up with someone, just do it. Yes, it’s hurts him, but dragging it out a lying about it only prolongs the suffering and makes him hurt worse longer.

        1. Former Diet Coke Addict*

          Yeah, pretty much. Love is blind (or I suppose in many cases sees only what it wants to see).

          A military homecoming for adults is, I suppose, not too bad. But I hate the dynamic for kids–it’s terribly hard for them to be separated from their parents for a long time to begin with and all that accompanies that–now they’re taken aback by Mom or Dad turning up out of nowhere and surprising them at school or a game? It sets up a weird dynamic where the kids can be afraid that their parent won’t always be there or might disappear just as quickly as they appeared, or send the message that the kids’ feelings and anticipation are not important or worthy of consideration, or horrid embarrassment for crying in public (a big concern for a lot of kids!). There’s also the idea that the homecoming is Surprise! Dad’s Home and then the actual reintegration being difficult can really be hard on kids.

          In my own experience they’re not popular or considered a good idea, and most counselors will recommend lots and lots of discussion around it to better prepare kids for what might not be all happy fun joy.

          1. Carpe Librarium*

            Surprise homecomings are best reserved for pets – it’s always going to be a surprise for them.

            Oh, how I love seeing animals practically wriggle out of their fur with joy.

        2. Laurel Gray*

          Marriage proposals at sporting events are so ick! Especially when it makes the jumbotron and they show the people watching at home. I once witnessed a marriage proposal at a restaurant on Valentine’s day and the bride-to-be was dressed like she was on her way to do hot yoga. I have no idea why she was dressed like that on V-day night but I know if she had a heads up she would have looked the part.

          1. Kelly L.*

            Oh, you know which surprise bugged me? There was some thing a few years ago where a guy sprung a surprise wedding on his fiancee. They were engaged, so she did really want to marry him, and by all appearances was really happy about it–but it would have not been a good moment for me. I would want to have some part in planning my own wedding, just to make sure I had invited everyone I wanted there, and was wearing something I’d be happy about wearing, and so on.

            1. Laurel Gray*

              Just the idea of someone going behind your back and planning an entire wedding for you and robbing you of the fun of taste testing wedding cakes and dinner menu items is in itself a crime.

          2. CheeryO*

            I was at a minor league baseball game a couple weeks ago, and the couple in front of us got engaged between innings. I felt so icky about it, because (1) we saw ourselves on the jumbotron before we realized what was happening and started doing all kinds of silly dancing and waving, which ended up being embarrassing, and (2) I had no idea what I was supposed to do with my face while watching the proposal (which took SO LONG)… he was crying, she was shaking, and even though she said yes and it was all very cute, it was SO WEIRD to be caught in the middle of it.

      3. hermit crab*

        The exception to the surprise military homecoming issue (which I totally agree with) is those videos of dogs seeing their returning humans again for the first time. In most cases, though, I guess it would be hard NOT to surprise a dog. :)

        1. HeyNonnyNonny*

          I love the dog ones! There is one with a schnauzer that gets so excited it faints.

      4. Ad Astra*

        I hate surprise military homecomings. I would never want to be caught off guard at such a huge moment, especially one that will immediately affect my day-to-day life. Not to mention, I can’t help but think of all those kids watching whose parents aren’t coming home.

        I’m fine with surprise public proposals, but you better know your boyfriend/girlfriend well enough to be sure that’s what they want.

      5. cv*

        I think the reason surprise military homecomings for children are a thing is that often the family doesn’t know exactly when a deployed person is going to be coming home, and it’s not uncommon for things to change last minute. So parents don’t tell their kids that Daddy thinks he might be coming home on Thursday because then it turns out to be next Tuesday, or weeks or months from now, or the person is still in a highly dangerous situation until they’re in the air on the plane home. Jerking a kid around about when they’ll see their parent over and over in a situation like that can be cruel, depending on the age of the kid and the particular circumstances, so some people decide it’s better not to tell their kids anything at all. And sometimes the spouse doesn’t even know the person is coming home until he or she lands in the US and they only have half a day to prepare themselves emotionally, much less prepare the kids.

        The viral video aspect of it is troubling to me in many ways, and I’m sure that there are often better ways than just having a parent show up with no warning, but it’s not always done for the “hey, wouldn’t it be a fun surprise?” effect.

        1. some1*

          I agree. I totally get why the parent surprises the kid, I just don’t get why anyone thinks filming it is a good idea.

          1. Judy*

            I can even see filming it. It’s the putting it out there for the entire world to see that I don’t think is a good idea.

      6. HRChick*

        I never like military homecoming surprises but always felt like it was a personal issue for me. Having a husband that has been deployed 4 times and still has a long way to go in his career, seeing those was very, very painful while he was overseas. I wanted to be happy for this gushing, crying happy family, but all I would really feel was, on a good day, an achy loneliness and on a bad day devastating sadness that my husband wasn’t home yet.

        Plus, it feels too much like propaganda. They’re cashing in on these people’s personal lives and his career to promote the military feel-good stuff. I’ve been a military wife for years, but it still bothers me for some reason.

    2. Christy*

      My girlfriend had to teach me about this. I loved the idea of surprises but I think I’ve finally come around to the idea that anticipation is better.

    3. Isben Takes Tea*

      That’s a really good point. They’re is a difference between spontaneity and surprise. My sister LOVES being spontaneous, but she really hates surprises. If I want to surprise her, I have to let her know well in advance that we’re having a mystery outing on such and such a day, and then actually give her all the details of what we’re doing the day before. That way she gets some fun anticipation without feeling that someone is taking control of her time.

    4. Lily in NYC*

      Good point! I remember seeing a video of parents who tricked their kids into thinking they were going on vacation to the beach but they were really going to Disney. They didn’t tell the kids until they pulled in to the parking lot. Sure they were excited, but I remember being beside myself with excitement for a few weeks before my first trip to Disney World as a little tyke. The anticipation is an important part of these things.

      1. some1*

        Omg! That video cracked me up. “We’ve been planning to go to Dick’s house for a really long time.”

      2. Cath in Canada*

        Heh, my friends have a hilarious video (which they did NOT put on the internet) of them telling their daughter that they were flying down to Disney that day. Instead of her being super excited like they imagined, she burst into tears because she was worried about who was going to feed the neighbourhood stray cats that she’d semi-adopted!

        1. Lily in NYC*

          That is so sweet and cute! Embarrassing confession: my sister and I used to spend summers with our grandparents in Spain. My parents put a nice pool in while we were away as a surprise, and my reaction was to be bummed because I had been looking forward to seeing the sunflowers I had planted there before I left (which had to be removed for the pool). To be fair, I was really young and I didn’t say it out loud and acted thrilled. I just didn’t care about having a pool – it was my sister who was begging for one.

    5. Clever Name*

      Yeah, I have to agree. I feel that surprises of this magnitude are sort of like pranks in that the pranker gets all the enjoyment and the prankee is gets flack if they don’t find it as amazingly funny as the pranker.

    6. Allison*

      Wow, I’ve actually never thought of it as a power trip, but you’re right. This and public proposals, where the proposer is getting all the glory for planning it, plus the public support for being *so* romantic, and the person being proposed to had better say yes and show appreciation or everyone will call them a jerk.

  19. Artemesia*

    This just screams ‘Inappropriate! NO NO NO’ to me. I had a much more negative reaction than Alison. I can see this seriously damaging the boyfriend at the office because it comes across as adolescent and clingy. And think twice about ‘surprise’ visits as the surprise is not always what you think it will be. PLenty of people would feel that a surprise visit was presumptuous even if they would welcome a visit. And a boss who would participate in this unless he knew the employee was engaged to this person at least is really an idiot. How does he know that the employee doesn’t have a local girlfriend? or that the distance relationship is a lot less certain than she claims? or that the woman who contacts him is not actually that stalker that is the last person he wants to see?

    It brings something much too personal into the workplace — don’t send clowns, bouquets of balloons on his birthday or singing greetings to his workplace either.

  20. nona*

    Plan a surprise outside of work, OP.

    Workdays tend to not go exactly as planned. I think it will be better to surprise him when he’s done with that for the day. :)

  21. Lily in NYC*

    I think this is a bad idea for most people unless you are a military person coming back from deployment and surprising a loved one. I love those videos of soldiers surprising their dogs (and their unsuspecting children at school, but the dog ones really get me).

    1. The IT Manager*

      I think the military returnee surprising people are a bad idea too especially in public or filmed so the entire world can see an emotional reunion that should be private.

      Now surprising pets on the other hand – totally not opposed to that.

      1. MashaKasha*

        Agree, I too was thinking about all the “owner surprises a dog” videos as I was scrolling through this thread. It’s super easy to surprise a dog, because a dog lives in the moment. Hell I used to surprise my dog each time I got home from work! Thing is, dogs love surprises. Most humans, errr not so much.

    2. Allison*

      I was just about to type a similar comment. Homecoming visits hit me right in the feels every time, but they’re pretty much the only people who can pull that off.

    3. Emmie*

      If I were active duty military returning home from deployment, I would never surprise my kids – as much as the videos make me tear up. I am too aware that I could die on future deployments, and that my kids would forever be thinking that their Mom would magically show up at school one day, walk in the door, appear at the park, etc…. I pass no judgement on others. This just isn’t for me.

  22. Chickaletta*

    Look, I wish my husband would surprise me more, I’ve never had a surprise about anything and it gets dull after a decade or two of being able to predict the other person’s every move from a mile away. But I think a surprise at work would be awkward. So, while I’m all for encouraging you to surprise him and keep the spark alive, I’d figure out another way to do it.

    1. CorpGal*

      I feel bad you don’t get surprises — I love little surprises…like flowers, the laundry being done without me having to ask for help, etc. But surprise vacations, drop-ins and other surprises that require large amounts of rescheduling or time are NOT even close to things I love.

      1. Shan*

        Agreed. I’ve been with my SO for over 2 years, and I usually plan everything we do (which I don’t mind). If he were to surprise me with a get-away, I think I’d freak out wondering if he planned everything thoroughly and it would take all of the fun out of it for me.

    2. OfficePrincess*

      Agreed. It wouldn’t have to be big, in fact, it preferably wouldn’t be huge, but a simple surprise now and then would be great. Only problem is he gets so excited he can’t keep anything a secret (most years I know my Christmas present within a day or two of him picking something out). Surprising me at work though would go over like a lead balloon. IF he could get in the building, he’d either have to sit in a chair at my desk while I basically ignored him, help me move boxes (because he’s not going to get to sit and watch that) or turn around and go home. I try to plan my work days so that I don’t spend extra time here. When I’m done I can leave, but until then I’ve got things to do.

  23. Mallory Janis Ian*

    My husband showed up as a surprise at my work way back when I’d first started a new job. I did not like it one bit. I was away from my desk, so he chatted with my co-workers while they tried to locate me. I was in the dean’s suite in the middle of a something that needed my attention. It wasn’t exactly an emergency, just a small nuisance that I needed other people’s input to fix. My husband is a great guy, and my coworkers are lovely people, but I just didn’t like the possibility that he could show up at random at my work and disrupt what I was working on. When I’m at work, I just want to focus on doing my job without the potential for surprise social obligations popping up (even from my beloved family).

  24. CAinUK*

    Folks have covered why this is a bad idea for your bf and his boss, but I wanted to mention why his might also be a bad idea for YOU, OP:

    If you are spending money and time to fly across the country to visit him, don’t you want to ensure he takes time off work and some notice so he can plan someone activities (like coordinating with friends he wants you to meet at dinner, or show you around, etc.)? Otherwise, you show up and YAY he gets a surprise but then everything else isn’t planned and you have to sit around while he works all day.

    TL;DR weigh up the value of the surprise vs. the value of planning quality time together

    1. KT*

      This! The surprise fun will wear off when you find out he’s actually booked solid and can’t spend time with you.

      1. Kelly L.*

        Yup. It’s a lot of time and money to lay out for a trip where you may not even get to see him much.

      2. MashaKasha*

        Well, that’s where his boss comes in. “Josh, you need to take the week of the 15th off.” – “but I don’t want to.” – “Oh trust me you do. Look, just take the damn thing off already.”

        lol sorry this whole thread has put me in a giggly mood, I guess.

    2. Nancy Drew*

      My thoughts exactly. Something like this would really upset me, apart from the work issue, because I would want to take time off work, show you around, and meet my friends.

    3. EvilQueenRegina*

      Yes, this. My relatives turned up to surprise me once and because I had no idea until they turned up on the doorstep, I wasn’t able to get the time off work and they had to entertain themselves. I advised them against doing that again.

  25. KT*

    I’m a big giant stick in the mud. I have a sharp divide between personal life and professional life. If a significant other showed up at my work (and I found out he had worked it out with my boss), I would be beyond uncomfortable and angry.

  26. Case of the Mondays*

    So, I’ve been part of one work surprise that involved a large group of out of town friends surprising an employee. Said employee worked in the laid back entertainment industry and his coworkers all got involved and it was really successful but such things are rare.

    I wouldn’t have a problem involving a boss if just to make sure the employee doesn’t get scheduled for a day off or for overtime that day. As an example, my husband just threw me a surprise party on a Saturday. The Saturday before, I agreed to go into work. I wouldn’t have minded at all if he had told my boss so that my boss would make sure on that Saturday I wasn’t volunteering for any extra work, screwing everything up.

    1. Case of the Mondays*

      Just to be clear, the making sure the schedule works part is for time he normally wouldn’t be at work and you are still planning your surprise for outside of the office. I think this also depends on how old you are. I loved surprises like this in my late teens early twenties. Now that I’m older, I want a say in when I use vacation time and how I spend my money and stuff.

      1. Andrea*

        I’m 24 and he’s 25. But agreed :) I’ll plan this out and talk to him in the coming months.

        I know it seems early but I’m using my money to go out there (saving up ALOT lol) and when he gets his vacation time, he’ll fly to NYC.

        He’s coming here this year in August. Then I won’t see him till the same timeframe next year so I figured I would go there in March:

        1) March 6 is his birthday
        2) It makes our LDR easier and stronger :)

  27. Ad Astra*

    I’m sure this OP is perfectly nice and has the best of intentions, but it’s a bad idea for managers to give outsiders access to their employees. If the visitor is someone the employee really doesn’t want to see, you’ve put your employee in an uncomfortable position. If the visitor is someone who’s been abusing, stalking, threatening, or otherwise scaring your employee, you may have put your employee in real danger.

    So managers, please remember to decline requests like these, even if they sound harmless and adorable.

    1. Nina*

      Yep, stalking crossed my mind, too. Not that OP is a stalker, but that stalkers and abusers use similar tactics when they’re trying to track someone down.

      1. Andrea*

        Not just stalkers. About 15 years ago, I worked as a legal researcher for a law firm, and it was sometimes my job to get information about certain individuals. (Usually after they had stopped making payments after having a judgment issued against them, and we were going about wage garnishment and needed to confirm whether they were still working at the last known place of employment.) Usually, all I had to do was call an employer, claim to be an SO or faraway relative or old friend planning a surprise, and I could get every detail I needed and more from various employers (sometimes they would even give me current place of employment). The best policy is not to give any information to anyone in such contexts, no matter who the caller claims to be.

  28. Margaret*

    In a college job (workstudy student employees, though I think this was during the summer when we were technically temps and working fulltime), a coworker’s boyfriend asked our boss to give her the day off, so he could surprise her with a date. From the work/professionalism standpoint, it worked because, since we were on campus, he knew our boss and the environment was casual enough that he (also a student there) could swing by and chat with his girlfriend and the rest of the office fairly regularly. So he was able to have a good sense of how the boss would see it, whether his girlfriend would have urgent work to do, etc. The only real problem in this case was that, because he went out of the way to even involve work to surprise the girlfriend, the office guessed that he was going to propose! And, though they actually are married now, the date in question was just a surprise to take her to a concert, just because.

    But if I were in a LDR, I would not appreciate a surprise visit. I’m introverted and a homebody, and if I plan time to be home by myself, nobody, even a SO that I love, would be a pleasant alternative. And in most situations (a job like I described above with relatively low expectations and knowing the boss/office pretty well being a very rare exception), not appropriate to involve the workplace in that way.

  29. L*

    You: “Boyfriend, I’d like to plan a surprise on your birthday. Can you take the day off?”

    Easy. Leave his job out of it. People see movies/youtube and think the dramatic is great. Being thoughtful is WAY better.

    1. Nina*

      That’s a great way to do it. You’re still planning a surprise for him, and you’re leaving the job concern out of the situation entirely.

      FWIW, I think the OP’s heart is in the right place and means well with this gesture, there’s just too many ways it can go wrong.

  30. Lunchy*

    OP, take it from someone who was also in a LDR – wait until after work.
    I actually surprised my boyfriend by flying to see him, roping his friend into driving me to his apartment, and waiting there until he came home from work. I called him and told him to open the door, but being the stick in the mud he is, he refused to open it because he didn’t see a point. Finally, I got fed up and just busted the door down and marched into his room. The look on his face was priceless. He just kept looking from his phone to me and back, saying, “I’M SO CONFUSED!”

    It turned out he’d had another stressful day at work, and me popping up really cheered him up. Can you really think of anything better than coming home after a tough day and finding the person you love waiting for you? Ignore the cynics saying you might not be together in 8 months. You know your guy (I would think, anyway), and you can decide if he’s cool with surprises.

    1. Emily*

      “You know your guy . . . and you can decide if he’s cool with surprises.”

      Totally true. This is one of those cases where I think you can truly say, “there are two kind of people in this world . . ” Some people love surprises. Some people loathe surprises. Sounds like this guy might be a surprise-lover—great! Save the thrill of the surprise for a time and space away from work, where he can react candidly and enjoy his gift. At the office, you risk falling into assorted professional pitfalls, but also putting a real damper on what could be a fun/sweet/romantic surprise.

  31. Andrea*

    Hello everyone!! :)

    I’m the one who wrote in. Read the replies and it was very helpful!!

    I re-evaluated things and agree that it wouldn’t be a good idea to see him at his job, but will just wait till afterwards and let him know a couple weeks before in little hints.

    The hotel I’m looking at is within walking distance from his job so I thought it be a plus. His vacation isn’t till the summer (anytime after July, once a year) so I thought to see him in March and celebrate his birthday and the few days after he’s done with work. As far as friends of his wanting to do anything? It’s unlikely because his small circle of friends are always busy. But you guys are right: anything can change with plans! :) So we’ll see.

    But thank you all for your advice! :) Very helpful!!

    1. Season Pass Holder*

      Yay! Good plan. BTW, if you ask his friends early enough maybe they won’t be busy

  32. Season Pass Holder*

    Amusement parks and the like take safety seriously, as well they should- people have died on some rides. I don’t think any manager would willingly invite this kind of distraction upon one of their operators. Or at least I *hope* they wouldn’t.

    1. nona*

      +1 I didn’t catch that he was a ride operator. Maybe I’m still nervous from the N.C. State Fair, but don’t distract him at all!!

  33. BritCred*

    My mother was actually quite friendly with my step fathers boss and once arranged for him to have a few days off without him knowing so they could go on holiday. The difference was the surprise didn’t happen at work and they already had a talking rapport so it wasn’t out of the blue.

  34. Sunshine Brite*

    Sorry, team stick-in-the-mud as well.
    -I hate surprises.
    -Rom-com moments are supposed to be left in the movies
    -It doesn’t sound like you know the boss at all
    -Boss can’t be on the hook if your boyfriend doesn’t want you there for whatever reason – personal/professional divide, concerns of abuse, rules with the ride, etc.
    -He might have other birthday plans made by then
    -A lot can happen between now and March
    -He might not have a place for you to stay at or want guests for whatever reason

    If you must surprise him, make sure to get a hotel where he lives and possibly a rental car depending on if he’s in the city or outside of it and have a ton of alternative ideas to check out if he’s busy so you still have a good trip.

    1. Andrea*

      I have a hotel in mind I’m staying at :)
      He would actually come after work to the hotel. It’s within walking distance from his job. A block or two.

      And I wouldn’t say you’re a stick in the mud :) and the job is in Downtown Las Vegas where there’s a lot to see so I’ll keep myself quite busy till he’s done with work :D

  35. The Other Dawn*

    Although I *think* that I would love a surprise like this, the reality is I probably wouldn’t. As it is, I get really annoyed when I don’t get to binge-watch The Golden Girls on Friday nights in my jammies, curled up with the cats, while I switch back and forth between the iPad and cell phone in order to maximize my Candy Crush lives. If I had a long-distance boyfriend or spouse that decided to crash my work place and I had to rearrange plans, clean the house in a hurry, feed another person (which means grocery shopping or eating out), or miss my Friday night ritual, I’d be pissed. Sure, I love the guy to pieces, but I don’t think I’d like to be ambushed like that. It feels so…demanding, I guess. Kind of like, “You have to pay attention to me for the next three days and just let everything else go.” But I’m crabby like that, so.

    1. The Other Dawn*

      Ack! Hit the button too soon.

      As a manager, I don’t want to be put in the position to have to make a decision like that. While I do know my team somewhat, I’m not privy to all the gory intimate details of their lives.

      One of my team members did this to her boyfriend, who works in another department here, and I kind of cringed when I heard what she was planning. She arranged it with his boss to have that Friday off and she told him when they got in the car to leave for work that they had the day off and they were driving to DC for weekend. Luckily he loved it, but I couldn’t help but wonder if he really felt ambushed and trapped. Especially because he’s in IT support; IT is usually swamped and it’s not usually predictable.

    2. Pam Poovey*

      While I don’t necessarily binge watch Golden Girls, I’m binge watching something on a Friday night with my cats and have the same strategy for Candy Crush while doing so. You just described my typical weekend night, so I really hope you weren’t just being facetious :)

  36. Karyn*

    Last February, I was talking to a good male friend of mine who lives in VA (I’m in OH), and we admitted to having regrets about never going out in college. It was a wine-induced nostalgia-fest. Casually, in the course of conversation, he asked me what I was doing that weekend. I said I planned to stay in my pajamas and try to get some work done on my novel. It was very casual, and by the next day, I’d put the conversation out of my mind.

    Fast forward to two days later, a Saturday. I was in my bathrobe in my room, having gotten out of the shower a few minutes earlier, and all of a sudden, my mother calls upstairs: “Karyn? George is here.”

    I come downstairs, and there is George, standing in my living room looking proud of himself. He goes, “Hey, what’s up?” As if I should have expected this! I look at him and go, “GET UPSTAIRS WE NEED TO HAVE A CONVERSATION PLS.”

    Cue me standing there in my bedroom, in my bathrobe, spitting tacks. I told him he might as well have come with a boombox and stood outside my house. It was an invasion, particularly because he knew I wanted to stay in and work on my writing, and because in no way had I indicated I wanted to try for a relationship NOW. Then he informs me that he hasn’t made plans for a place to stay (WITH his two dogs, BTW). I told him I didn’t care what he did, but he wasn’t staying at my place – I live with my parents right now, and this was just as much a surprise for them as it was for me.

    To this day, I still don’t know what he was thinking. Obviously, he had a plan for how this would work out, but I think it involved me swooning and telling him how romantic it all was. We don’t talk much anymore, though. Which is a shame because he was one of my best friends… but I think he was so embarrassed by the entire thing that he has little to say.

    1. MsM*

      He brought the dogs?! I can see the thought process that went into his “surprise” – although I am 100% in agreement with you, and it sounds like you handled explaining why it was not okay like a boss – but even the most love-addled, romance movie-deluded would-be lover has to know furry houseguests are something you clear in advance.

      Sucks about the friendship, but all in all, I’d say it’s a good thing you two never gave it a shot in college.

      1. Karyn*

        I was flabbergasted. I understood the thought process he had with the surprise (meaning I get what he was thinking but how he didn’t realize this was a bad idea is beyond me) but the dogs. He knows we have like thirteen cats in this house and a dog of our own. SERIOUSLY DUDE.

        And yeah, I told him he would be staying in a hotel which I would not be visiting and I was sorry he’d wasted the gas on the drive from VA to OH, but maaaaaaan, I was not going to reward bad behavior.

  37. Elad*

    This is a bad idea.
    I once saw a movie in which the girlfriend comes into the apartment of her boyfriend on his birthday for a suprise visid only to catches him cheating on her with another woman.

    1. Andrea*

      Oh no!! O.O

      Well, I know him very well and I know he wouldn’t cheat and neither would I.

      We agreed that if either felt the need to stray at any point, we’ll tell the other person and end things right then and there and not be too angry about it because it was said before hand.

      No lies, no actions were made (and karma is a real you-know-what) but I get the idea :)

      1. fposte*

        Yeah, I don’t think just because it went badly in a movie means that it’s going to be doomed. I think you’re being very sensible in thinking through the pros and cons, and this is a guy you seem to know pretty well and will know even better come the time. I think people have made a good point about surprises being more for the surpriser than the surprisee, but as long as you know he enjoys that kind of thing I think it’s fine to have your fun doing it too.

        Just don’t do it at his work :-).

        1. Andrea*

          Thank you :) I am definitely not doing this at his job.

          And I asked his really good friend about it and she said she’ll help in anyway possible to make this one of his best birthdays ever!

          And he also told me that he may actually be starting work elsewhere by November.

          A long time friend of his is starting up a business and they’re considering a partnership in it together.

          Here’s hoping things go well with their idea. And if it does work, he’ll have more availability in seeing me more often. But he’s not quitting his job just yet but will eventually do part time hours instead of full.

  38. Applesauced*

    The ONLY time I’ve seen this work was my parents – for her 50th Birthday my dad planned a surprise trip for my mom (a place they’d been wanting to go and talking about doing a few months later) She’d been at her job for 10 years so he knew her boss and asked for her to have a Friday off, got my sister and I to pack a bag and showed up at the office to take her on a long weekend!

  39. Anongal*

    Do you think the same advice applies re asking a manager to give a significant other a day off for their birthday (with lots of advance notice)? I’d like to surprise my husband by having him wake up on his birthday thinking he’s going to work. I usually drop him off on the way in and it would be fun to just drive past his office, tell him he’s got a long weekend, and then head off for a 3-day getaway.

    1. The IT Manager*

      I would still hate this. You know your husband, but Margo Victory (below) points out why this still might be a bad idea – maybe there’s something at work that needs to/should be done at work on his birthday and your husband was not consulted before you and his boss decided to give him a day off.

      1. MsM*

        And even if the long weekend does turn out to be good timing, he may not want a getaway so much as a chance to sleep for the next three days, or to spend his birthday with his buddies. As with most of these questions, this is a “know your significant other” thing, but if I’m going somewhere, I want to be able to plan for it well in advance.

    2. fposte*

      Even more so, I’d say. That’s not just asking to drop by, that’s asking to change schedules. I’d be pretty taken aback to get a schedule-change request from somebody who didn’t work for me.

  40. Margo Victory*

    Eh, I think the part about not knowing someone’s working life still holds. Even for significant others who share everything and have been together forever, you still don’t know everything about their daily working life.

    We don’t tell even those closest to us every little thing on our plate at work, every deadline, every necessary phone call, every I-need-to-finish-these-small-things-this-week-or-next-week-they’ll-multiply-like-gremlins. That is tedious information we rarely share, but it’s very relevant to determining good/bad surprises. Spending 3 days on an otherwise fun getaway while a list of all the things I now have to unexpectedly push to Monday runs in the back of my head OR much more relaxing 3-day fun getaway I knew enough about in advance so I could plan for it and clear my schedule? I know which one sounds more fun and romantic to me.

    “I want to take you away for a surprise 3-day vacation.” There is nothing wrong with leaving the destination as the only mystery. That’s enough of a surprise to still be fun.

  41. Mary in Texas*

    I have a punctuation question. Twice in this post, Alison wrote “Who knows.” Should there be a question mark (“?”) instead of a period at the end of this sentence? I’ve been wondering that a lot lately. I see sentenences when read are in the form of a question, but no question mark. Thoughts???

    1. Ask a Manager* Post author

      Yes, theoretically there should be. I used a period because this is informal writing and I wanted to emphasize that I’m saying it as a statement more than a question (more like “we can’t know”), but if this were formal writing, it should be a question mark.

  42. Student*

    There are times for surprise visits.

    Any time you have to fly cross-country to hang out with someone is NOT a time for a surprise visit. Please talk to your boyfriend and let him know you’re coming.

    There’s a chance that the surprise could work out great, either at or outside work. There’s a good chance it’ll reflect badly on him at work. In addition to comments already included, birthdays are a cultural thing, not a universal thing; you could be making him look bad to his boss merely by making a big deal about his birthday. Some of us (self included) regard birthdays as a children’s event, not something for adults.

    There’s also a chance that he will make other plans if he doesn’t know you are coming. If he’s a big birthday person, I’d say it’s rather likely. Wouldn’t you feel terrible if you showed up and he’s gone on a camping trip with his buddies? Or to an out of town sport event, or to meet up with his parents, or any other number of things he might do for his own birthday? Some stuff you could likely tag along with – some you’d probably be left sitting alone at a hotel.

    1. Andrea*

      He’s actually not big on his birthday :( like going out to an event, movies, things like that. He thinks of it as another day.

      I sent for him through this gift basket company (Shari’s Berries) a box of chocolate covered strawberries (his favorite) with 3 brownie cupcakes with candles in them with a card, and had his favorite take out food paid for and he just needed to pick it up. And he just wanted to spend the rest of his birthday on Skype with me, even though I told him he should go out lol

  43. Nancie*

    Oh good. Now I’m going to have nightmares about the girlfriend who decided she wanted to surprise one of my coworkers, her boyfriend, at work on his birthday. She’d asked our manager if she could bring in a cake and a singing telegram.

    What she left out, was that the “singing telegram” was actually a male, cross-dressing, stripper. That was all kinds of uncomfortable, and I felt far worse for my manager than I did for either the gf or my coworker.

    1. ThursdaysGeek*

      Yeah, the strip-tease Miss Piggy* sent to my workplace for a birthday surprise for some co-worker (years ago) was all sorts of awkward for all involved.

      *She was anatomically correct…for a pig!

  44. mdv*

    My younger brother and I just did a surprise party for my mom’s birthday this weekend, with assistance from stepdad — brother’s idea to fly in from San Francisco for a long weekend, and to then do a surprise party. Stepdad was in charge of invitations and the day-of distractions, while I organized the food and made sure we got everything set up in what seemed like a VERY SHORT hour. It was a lot of fun, and went over very well!

  45. Chris*

    My friend called his girlfriend’s boss, and got them to give her several days off. Then he let her get ready for work, proposed to her, and then took her to Vegas for the weekend. So I think it’s a YMMV situation. If you’re sure the workplace would find this reasonable, no worries. Some places, thinking big corporations/banks, etc, might not appreciate it.

    1. HRG*

      I honestly think this is awesome. I’m a spontaneous person and would be 100% into this happening.

  46. Elle*

    Am I the only one who got super stick in the mud and thought -who says you’ll be together in March 2016?- Just sayin’…

  47. SevenSixOne*

    ” Lots of people don’t want surprise social visitors showing up at their work at all, no matter how much they like the people themselves.”

    If it were up to me, I’d never have social visitors at work AT ALL– meeting someone for lunch stresses me out, even when we plan it days or weeks in advance.

  48. mel*

    Aw man, having people visit at work is the worst thing ever. I mean, yeah, hanging out with friends is SO MUCH BETTER than having strangers at best ignoring you and at worst yelling at you all day… but you won’t be hanging out. You can’t have a conversation because everything is recorded and witnessed with harsh scrutiny. And even if you try to chat anyway, it’s stressful to keep looking over your shoulder for the boss or for a quiet customer who thinks you’re undeserving of eye contact or bottled water, let alone friendship.

    And then you’ll awkwardly part, and his day gets agonizingly longer because now he knows that there’s something good out there waiting for him while he’s selling his life for minimum wage.

    I’m just saying, if you’ve got a work surprise, hopefully it’s at the very end of a shift and more than just a “heeeeyyyyyyy!”

  49. HRG*

    Unpopular opinion but I would absolutely love this. Love the idea of being surprised at work because it would truly be a surprise, wouldn’t even be thinking about my boyfriend and then BAM! There he would be! Maybe with flowers or something. aw. My bf and I have been together about a year and a half.. we were in an LDR until a month ago when he moved to my city. I would’ve loved this though, and my manager definitely would’ve gotten into it. I guess it depends on how you think your bf would react and what you know, if anything, about his manager.

    1. HRG*

      For the record, my boyfriend and manager and coworkers had met a few times at happy hours and such so it would’ve been less weird in my hypothetical for him to reach out and ask about surprising me. Have you ever been to his work before or met his manager? That makes a difference too, I think.

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