“My Crush on my Boss is Crushing Me”

I work for a very small organization that has one part time and two full time employees. The work we do is very demanding and stressful, but the three of us get along very well both personally and professionally. It is honestly the best job I’ve ever had. My problem is, I seem to have developed an enormous crush on my boss. He’s about my age, single, and we share a great deal in common. I admire his passion for the work that he does as well as his intelligence and kindness. I’m also getting the feeling that he might be interested in me as well. It’s gotten to the point where he walks into the room and I can feel my face flush and my mouth go dry. I’m not the kind of person who would normally even think about dating her boss, and I know it’s not a good idea, but I can’t stop fantasizing about it anyway. Am I crazy for thinking I could make a relationship with my boss work? If I am, how can I get him out of my head when I have to see him everyday? — Hot for Boss Man

I wouldn’t say you’re crazy for thinking you can make a relationship with your boss work, but I would definitely think long and hard about the possible repercussions of dating him. It makes sense that you’d have feelings for someone you spend so much time with in a high-pressured, very close-knit environment. That you’re both single, close in age, have a lot in common, and that you find him to be an intelligent and kind person can only sweeten the deal, I’m sure. And while it may be tempting to act on these feelings — especially if you suspect they’re mutual — the fact is that doing so would absolutely put your job — a job you say you love — in serious jeopardy.

First of all, even if things work out between you, the dynamic in your office would certainly change. There are only three of you, so it’s not like you have the luxury of moving to another department or avoiding him at the office. You’d still be his subordinate, which could complicate the boundaries of your relationship both in and out of work. Then, there’s your third co-worker to think about. As it stands, the three of you work well together — a dynamic I’m sure in necessary in what you describe as a demanding work environment. What happens if/when s/he feels awkward about the romantic relationship blossoming between her two only co-workers? What happens if she feels the boss is giving you preferential treatment? What if she decides to leave and your boss if forced to find a replacement who may not gel as well with you both? Or … what if your boss decides that rather than let her leave, you should be the one to find a new job? How do you suppose that might affect your relationship?

And then there’s the possibility of things not working out between you — of you two giving dating a shot and discovering the bond you share in the office and even as friends doesn’t transfer to a romantic relationship. In a perfect world, you’d be able to move seamlessly from dating partners back to strictly work partners, but you’re only human and this world isn’t perfect. Emotional investments can make transitions like that challenging — and all the more so if your work relationship is that of supervisor/subordinate.

Bottom line: are you prepared to give up your job for a chance at a relationship with your boss? It may not come to that, of course, but the possibility is very real, and something you need to be ready to deal with. If you are, then go for it. Who knows — maybe this guy is your soul-mate or whatever. Maybe the reason you ended up at this position was to meet him, fall in love, get married and start a life together. Jobs, after all, come and go (though one can argue that so do boyfriends…), but the love of your life — well, that usually just comes along once. Of course, pursuing your boss doesn’t guarantee that he will be interested in pursuing you back. Even if he is interested in you, he may decide the risk is not worth it and decline any advances from you. So, in addition to the risk of your job, you need to be prepared for the risk of rejection, too.

If it all seems like too big of a chance to take and you’d rather just brush the crush aside, I’d give it another month or so of trying to get him out of your head in that way before making any rash moves. Make a list in your journal of all the reasons dating him would screw things up. Try to imagine him as a terrible kisser and bad in bed. Be sure not to dress in provocative ways or otherwise flirt with him or engage him in ways that could be misconstrued.

If, after a month or so, you’re feeling more turned on by him than ever — and you suspect the feeling might be mutual — it could behoove you to have a private discussion with him about these feelings. Holding the secret in gives it a sort of power that can continue to magnify. And while there’s risk in confessing the crush — like embarrassment or awkwardness — there’s a good chance that by releasing the secret, it will feel less illicit and will relinquish its power over you. I wouldn’t make the confession a big deal, though. Since you’re friendly outside of the office, I might invite him for a cup of coffee before work and say something like, “I’m sure it’s because we spend so many hours of the day together, but lately I’ve developed feelings for you that are not strictly professional or platonic in nature, and I wanted to let you know because while I have no intention of acting on them, I didn’t want you to get the impression that I do. I love my job, I love our work dynamic and I would never want to do anything to jeopardize either, so until these feelings pass — as I’m sure they will soon — I hope you’ll be patient with me as I work through them.” Professional, to the point, and not terribly sexy — three major points to hit if you what you want is to move on and get over it.

*If you have a relationship/dating question I can help answer, send me your letters at wendy@dearwendy.com and be sure to follow me on Twitter.


  1. Wendy, your advice to LW is spot on!

    I’m curious LW, what signs are you getting that your crush for the boss is potentially reciprocated? Is his style of communication with you different from that of the other co-worker or are you getting more leeway? How frequent are his non-work related conversations with you? Are you getting solo invitations to lunch or other social events outside the workday?

    If your company was big enough, I would say ask for a transfer and see what happens then. Yet since your company is so small, make sure you’re not evaluating your crush through the rosy haze of potential. If you feel the possibility of romance outweighs the career established so far, I would start a potential job search as a safety net before you follow through with revealing your crush as Wendy suggested.

    Good Luck!

  2. ReginaRey says:

    I definitely think you need to weigh the potential pros against the inevitable cons if you were to pursue a relationship. If it DOES work out, there’s really no doubt that you would have to leave your job – in such an intimate organization, intimate relationships will make the work dynamic pretty awkward for the remaining employees, and could have a lot of negative effects on your romantic relationship. You would have to take direction, be supervised by, and report to someone who you have sleepovers with! It’s not very healthy for the romantic side of your relationship.

    BUT, from what you’ve written I don’t think you should necessarily ignore it or try to quash it. Like Wendy said, give it a bit more time. If you still can’t get him out of your head, I think you need to very tenderly address your feelings with him (outside the office!). People end up with people who they have things in common with – be it work, passions, personality, intelligence, values, what have you. You seem to have developed feelings for him for the right reasons, and you would not be the first person to meet your future partner at the office. People who work together naturally have a good deal of things in common, which is a great foundation for building a relationship. Just be prepared to sacrifice your job if it comes to it.

    1. missarissa says:

      I don’t know about leaving her job if it works out…

      I’m inclined to think that the smallness of the firm makes it MORE ok to date the boss and survive.

      If this is her dream job that is the best she’s had, I’m going to assume she and the boss are the full time employee and the third employee is the parttime employee. If so, then he is probably the owner of the company and it is his brainchild, and she is helping it happen. If they do pursue a successful relationship and he is a modern, enlightened man, then eventually they will grow to be more like partners in the endeavor, and less like boss-man and subordinate employee. This can’t happen in a big firm with a bureacracy, because of sexual discrimination problems, as well as others. If she’s basically the only other employee (save the parttime worker who, I’m sorry, by virtue of being parttime, is on another track) , there are no sexual discrimination problems if she grows into a role as his partner, both inside and outside of work.

      That said, if the relationship sours, it makes it much much more difficult to continue because it’s just the two of them.

      1. sweetleaf says:

        Totally agree. I work at a relatively small company (about 150 employees) Here, there are about 10 married couples, most of which met here at the company. Some are in upper management while their SO do things on a smaller scale. Anything is possible. And as a single gal, I’m hoping they hire my match soon 😉

  3. gosh, i don’t envy the LWs position in having that conversation!

  4. I think the risks out weigh the benefits. Being such a small office, the possibility of rejection could be just as, if not more, awkward for everyone than if you two did start dating. He would know you were into him, so would probably act a little different around you. Your office dynamic would change. Maybe you all would stop going out for happy hour or whatever it is you do socially together. Then you would feel awkward because you confessed your feelings for him and he rejected you, and you’d blame yourself for the change in office dynamic. It could affect work habits or productivity. Then he’d feel awkward bringing it up, scared to address the issues because he’d be afraid you’d think he was trying to get rid of you because you like him and he doesn’t like you.

    Then on the flip side, let’s say you two do get together. Could you be with this guy pretty much 24/7? Yeah, there’s the phase when you’re dating and you still live separately, so you both have your alone time. But what if things progress? What if you decide to do what most couples end up doing – moving in together? Can you wake up with the guy, go to work with him, be with him (and take orders from him) all day, go home together, go to bed together, then wake up and do it all over again? As much love as two people can be in, spending THAT much time together is likely going to mess with you. Everyone, I don’t care who you are, needs their space. Where do you go to escape? Out shopping, maybe out with friends. That kills, what, a few hours. You would ultimately feel there was no escaping, and either you or he would have to choose between a) breaking up. Then you’re back to my former example of having things be awkward in the office, or b) quitting your job and looking for another one (in this lovely job-market we live in), in which case whoever did would end up resenting the other one and you’d ultimately end up doing Option A, but it would be worse because one of you would be out of a job.

    You can use these overly-dramatic examples of potential outcomes to try and convince yourself to let this one slide as you wait it out, as Wendy suggested.

  5. As someone who started a romantic relationship with someone who was not my boss, but supervised me on a couple of projects, I can say from experience that it is not a sustainable situation. We worked for a much larger company, and didn’t even have to work together every day, but it was clear from day one that we wouldn’t be able to keep working together forever. It was impossible to leave work at work, and all our work arguments became fights and all our fights became work arguments… it was not a good dynamic at all! We stuck that out for over a year before I finally moved to another job, but it put a lot of stress on our relationship from the get-go, and it’s been a lot easier since I left. I can’t even imagine trying to make that work in such a small company!

    From my experience, if you want things to work out well in both short and long term, you can either pursue the crush OR continue working there. Odds are if you do both at once you’ll ruin both your job and your relationship.

  6. BoomChakaLaka says:

    Yeah, the cons really outweigh the pros in this situation. I feel like in any other scenario, it would be easy to just say “Go for it,” but you need to think long and hard about the consequences of your actions here. If you love what you do (you say “It’s the best job I’ve ever had”), I don’t think it would be the best thing to potentially jeopardize that for a chance with your boss, especially since a good job (great environment, benefits, etc) is really hard to come by.

    I would certainly take Wendy’s advice and sit on it for a bit. Then follow that up with a conversation outside of the office where you professionally discuss your feelings and see if you guys can work something out. At the end of the day, I hope you are still able to keep a your great boss and great work environment.

  7. WatersEdge says:

    I think you should let things stay the way they are for a while. As ReginaRay said, you do seem to like this guy for all the right reasons. It’s nice to hear someone admire someone else’s good character as a reason to want to date them! He sounds like a great guy, and those are few and far between.

    I think this situation will naturally come to a head in its own time. Hopefully if you keep working together and keep building a bond before you pursue each other, it will be more likely that you’ll have a solid foundation for a long-lasting relationship. Or maybe one of you will meet someone else and it’ll resolve itself in that way.

    Just be prepared that if you do start to be involved with your boss in any personal way, the clock begins ticking toward the day you need to find a new job. Whether things go great or whether they go badly, you can’t work together and date for very long in such a small office.

  8. Hoo boy.

    I’ve been there. Except – I was the boss in the situation. And, speaking from this point of view, I wish it had never started to begin with. Oh, sure, it was fun and great while it lasted.

    But after it blew up spectacularly (and it did – although that was due to his drinking…it’s a long story) we had to continue to work together. And it was a very small environment as well. In all honesty, it was probably one of the worst experiences I’ve ever been through. He treated me like crap and when I would call him on it, he always took it personally. I tried, and mostly succeeded, to treat him the same as I did my other employees even though he was the one that ended it. I never let him see how much it rattled me or that I went home crying everyday for about 5 months. I couldn’t fire him because my boss didn’t see anything wrong since it was a personal issue. I was stuck and he knew it.

    Now, I’m not saying that things will be this awful for your boss. But things COULD be this bad for you. If I had to do it all over again, I wouldn’t. You couldn’t pay me to put myself through all of that. So my advice is to think about it before you pursue anything. If you can’t get him out of your head, find something else to distract yourself with. Find classes or take part in other hobbies. Maybe you’ll meet someone else that you’ll feel just as attracted to!

  9. spaceboy761 says:

    As someone who actually tried this in 2003, I’ll say that it can work under the right circumstances. My situation was a little different since when we held the same position when started dating and I got a very unexpected promotion (due to a mass exodus on our Philly desk, the NY manager transferring to Philly, and me taking over in NY) to become my ex’s boss. Our division was seven people and she was the only woman, FWIW. If you set ground rules right away with everybody, it’s not impossible. The relationship ended on decentish terms not relating at all to work, and she actually got fired before we broke up (not by me).

    And here’s the monkey wrench. A three-person office is perhaps the worst place humanly imaginable for an office romance. That is like some shit out of a Sartre novel that develops the concept of existential hell. Previous commenters have said that jobs come and go and relationships come and go. You have to make up your mind between the two BEFORE initiating any ‘let’s see what’s there’ conversation with your hot boss. Either way, you’ll be putting a ton of pressure on the aspect (job or relationship) that remains because you’ll be sacrificing one to invest in the other.

    Having that said, getting a clear idea of how interested in you by seeing how see responds to mixedish signals without having a big talk would be really helpful in making your decision. I know that that’s typically AWFUL AWFUL advice, but being left with neither the boyfriend nor the job is a real possibility here and something you want to avoid at all costs, even if it means blowing on the dice a little bit. You would have to be something of a relationship black belt to pull this off, but man, it would really help your decision.

    1. caitie_didn't says:

      I agree about the Satre….this is a modern day “No Exit” for SURE.

      1. spaceboy761 says:

        I pride myself on my ability to reference literary works I’ve never read.

      2. demoiselle says:

        Except they’re all alive!!

  10. I agree with Wendy’s advice until the last paragraph. If I were wait out the crush and ultimately decided that I would not want to pursue any type of relationship, I wouldn’t tell the boss my feelings. At that point unless they are affecting your job performance, they are irrelevant and he has no need to know. I feel telling your boss would just make him uncomfortable, and could still have the power affect the LW’s work environment. My question is what would the goal of that conversation be. To make her feel better about revealing the secret? While communication is important in relationships, some things are better left unspoken among coworkers or bosses!

    1. I completely agree! Tell a friend! Talking about the crush will help you get over it (or at least, it will probably help tone it down) but you should talk about it with an outside friend, someone who has little/no contact with the people you work with.

      1. Yeh I agree. I see no reason to tell the boss. I would talk about it to my friends and just wait for the feelings to subside. Try to get interested in other guys in the meantime.

  11. In my experience, relationships that start between a person in authority and a person below them tend to keep that dynamic well into the relationship. I don’t know very many people who started dating their boss, but I do know quite a few couples that developed from a professor/student relationship. And all of their relationships have a really weird power imbalance that is strange to watch. Obviously, not all boss/employee or teacher/student relationships go this way, but I do think its important to consider how the professional relationship you’ve cultivated would translate into a romantic one. Could he be too used to being in charge?

    Also, even if you are very good about keeping everything even outside your job, he would still be your boss. And when you have a romantic relationship, it might be really, really annoying when he asks you to do his bitchwork, corrects you, or reprimands you. I guess I just prefer my boyfriend to be an outlet that I can discuss work stresses with, not a part of it.

    1. spaceboy761 says:

      Not every relationship like this goes that way. My office romance ex treated me like a manbitch while we were working in the same capacity and not dating, treated me like a manbitch while we were working in the same capacity and had started dating, and treated me like a manbitch while I was her boss and we were still dating. I LIKES EM FEISTY!!!

    2. Agreed. A big component of a successful relationship is both parties being on the same page / level / “place”…when one is always dominating the other or taking care of the other it won’t last.

  12. demoiselle says:

    Wendy’s advice is spot on. Work relationships are really, really tricky. And even when you do everything right, there can be unexpected consequences.

    We see lots of work-romance letters, so I’ll share my family story:

    Even when a situation seems like it’s fairly “safe,” you have to be very careful about confessing you love your boss. My father was twenty-plus years older than my mother and (unhappily, it turned out) married, with grown kids. My mother fell in love with him on the job, and never let on how she felt. Then, he announced that he was going to take a new job in a different city across the country. He was resigning and moving away imminently.

    The thought that my dad would soon be gone and that she’d never confessed her feelings got to mom. And it seemed safe. He was about to move across the country. So she told him that she’d fallen in love with him. He got very quiet, and sent her away from his office.

    Mom was surprised. She’d expected him to tell her she was a silly young woman (or something) and that he didn’t feel a thing. She was bewildered by his strange, silent response. Then, a few hours later, he called her back to his office, told her he’d fallen in love with her too.

    Within three weeks, he’d already filed for a divorce. Needless to say, there was no longer any question of him moving across the country for a new job. He turned it down. I believe my dad transferred my mother out of his department so he was no longer her supervisor. My parents got married when his divorce was finalized, and moved to a new city themselves to start anew professionally, working apart. And here I am.

    It was a pretty good marriage, and my parents were both terrific for me. I know that they did the best they could in the situation. They did not have an extramarital affair–not in the sexual sense, anyway. They did not have a long, drawn out emotional affair. As soon as they admitted how they felt, he made his choice and ended his marriage. There was no long, dragged out trauma with his wife. My parents never went on a date until after he had filed for divorce. His kids were all adults and had all moved out on their own. He and his wife had previously discussed divorcing, but just hadn’t done it yet (in fact, I believe he had even been planning to make the move for the new job ALONE).

    But the way their relationship started did not endear my mother or my father to his older kids. They assumed he had an affair. His ex-wife, who had been very happy to get divorced, was NOT happy that my dad married a younger woman and had a baby. She made her kids choose between dad and her–which wounded my dad terribly, because he’d really believed they’d understand how unhappy he and his first wife had been, and would have been happy for him. Years later, one of his grandkids–who hadn’t even been born when my parents met and whose father actually WAS a flagrant cheat who was moving back and forth between wife and mistress–decided he HATED his grandfather (it was easier than hating his own father). Meanwhile, I never got to have a strong relationship with my half-siblings, because to them I wasn’t really one of the family, while I grew up believing that I WAS.

    It wasn’t until thirty years later, after the ex-wife had passed away and when my dad was terminally ill, that my parents were able to explain to his older kids that there had been no extramarital affair. That fact, and the way my mom cared for my ill father and welcomed them into our home for as long as they wanted to stay, despite their previous estrangement, made them finally *truly* realize how much she loved him (that she wasn’t a gold-digging younger woman, after all).

    The morale of the story for me has always been that you can be as careful as you possibly can with a work romance, and it can still have unforeseen consequences. You can do everything as right-as-possible when you fall in love with a married person–but the fallout can still be devastating. And everyone pays the price–even people who aren’t yet born.

    Good luck, LW–I hope that your situation works out well. And to future readers who are in a situation more like my parents’, I hope that my family’s story is useful.

    1. I can empathize with your situation as my family has a lot of those issues going on as well just not for the same reason. It really is tough – I’m glad the truth was told and accepted before the end.

      1. demoiselle says:

        It is worth noting, though, that although the truth came out in the end and made my *siblings* feel better about my mom and dad, it did not repair the relationship or make us into a family. Functionally, now I have only my mother-I can’t count on anyone else being there for me. And when one kid out of dad’s quite-a-few others has mistreated my mother, the others can only bring themselves to disapprove silently.

        I hope that your family can pull together better than mine did. I know that there are many families that do handle this situation–and much worse ones–better than mine did. My dad’s ex did everything she could to estrange us all. And though she apologized before she died and publicly tried to fix things, it was too late. (I will note, though, that the few times we met, she was flawlessly kind to me.)

    2. spaceboy761 says:

      I wish that my creation story was that dramatic and uplifting. My parents just met on the job and started banging. 🙁

      1. demoiselle says:

        It seems to have worked out in your favor, at least, spaceboy. I’m glad you think of my family’s story as uplifting. I tend to think of it as a Tragicomedy of Errors. 🙂

      2. spaceboy761, you rock…I swear half the time i just scan the comments for your Gravatar so i know which comments to read… 🙂

  13. Ouch, this is a tough one.
    I don’t have experience with dating a boss or supervisor, BUT I do have several experiences where I got too close to my boss, iow, became too friendly, too confident & BOTH times it back fired on me really bad!
    The first time it happened it was with two male bosses who would joke around with me all the time, as my *friends*, including dates I’d go on, parties I went to, etc…Then they started to tell me to respect the boundaries of work & the fact that they are my bosses. Um…ok? I ended up quitting because the tension got very bad.
    Now it’s with my current boss. She’s a woman, & kept saying she wanted to be my “mentor”, we developed a very close relationship, talk about private/personal things, I felt I could trust her…
    I guess I didn’t learn my lesson the first time because at this point, I am looking for another job. In the recent months she has become so unbearable, has crossed the line SO many times, including throwing a file at me…The last “out” we had was when I requested a day off bc one of my very good, long-time, friends from another country (that I hadn’t seen in two years) was in town for her birthday & only for a few days. My boss had known for a WEEK that I needed that day off…Then she came up with I couldn’t take the whole day off only half the day. I said, ok that’s fine, no problem…
    That day I got to work & 20 mins before I was scheduled to leave she informed me that I couldn’t leave because she had told her boss early that morning that I would help him out in his office. (UMMMM she waited 4 hours to inform me that she signed me up for smg!!)
    I began to ask her how could that be? etc…Long story short, she began yelling at me saying I made my choice, “my friends are obv. more important then my job”, & my decision was duly noted. (Lets note I’ve been a BEYOND loyal employee, am only a part-timer, & even showed up to work the day after I got into a car accident because she was in DIRE need of my assistance).
    So really point is, be careful. I know not everyone is like my two examples, but it’s so difficult when it pertains to work, ESPECIALLY if they have power over you. But weigh your options, if you’re ok with maybe having to quit if things don’t work out, if it’s worth it, then go for it. I believe in gut feelings, if you think this guy is truly worth it, go for it. Just recognize their may* be consequences…

    1. BoomChakaLaka says:

      That sounds horrible! Do you see a common personality trait with these bosses? Maybe you should keep an eye out for that on your next hunt.

      I have usually “tried” to get close to my bosses, but the relationship truly flourishes when I’m not working with them, rather than during my tenure. I would only advise you to know your limits, don’t share too much, keep it professional in the boundaries of work.

      1. Yes. I learned my lesson. Honestly the common trait I could pick up is that both times they wanted to “mentor” me & keep me close to them, for w/e reason. & I fell into the trap trusting them because both of them are a good 15-20 yrs older than me.
        Next job, I will definitely be more cautious I no matter what, refrain from getting to close/personal.
        But yeah, right now, the tension in my job is pretty bad.

  14. Christina says:

    I let work crushes go and don’t act on them because I know they come up just because of the close work environment. Mine usually last about 2 weeks, I get nervous around them and spend too much time thinking about them and then it just fizzles out. Yours probably will too. It’s fun for awhile and then they are just someone you used to have a crush on and working together gets easier. If he is feeling the same way he may just be letting it go too just to keep the work environment going well. Enjoy your crush but don’t act on it. I think the one month rule is great. It lets you put off the decision for action until later and by then you’ll know if you still feel as strongly, if he is interested enough to approach you and whether a relationship would be worth the change it would make to your great job.

    1. That’s a good point. It’s kind of like camp crushes or study abroad crushes….when somebody seems so attractive for that period of time you’re spending so much time with them, even though in retrospect, you can see that they wouldn’t really be a match or someone you’d go for if you hadn’t been in this situation. Work crushes can be really fun, and its definitely more exciting to be sorting through files when you can feel the sexual tension radiating….I’d enjoy it while it lasts and not say anything. He can make a move if he wants to.

      1. haha camp crushes or study abroad! I totally know what you mean. I had a crush on this guy when I was studying abroad, but I had a boyfriend back home so I never acted on it. I found out later that he was bipolar so I don’t think it would’ve ever truely worked. Crushes are fun while they last…

      2. ReginaRey says:

        I’m still with my study abroad crush 2 years later haha! But yeah, the majority of the time it’s just the magic of where you are making you believe you’re into someone.

      3. I had the biggest crush on this guy I studied abroad with last time… there were only 8 of us on the trip, all living together in a pretty isolated environment, and the sexual tension between us just grew and grew until we couldn’t stand it anymore. We made out one time, but nothing else ever happened because we were constantly surrounded by everyone else. We almost went on a trip to London together after it ended, but it ended up falling through because I couldn’t afford it….to this day I still wonder how that would’ve went! As soon as I got home, I lost all interest. I mean, he’s a cool guy, and he’s cute, but he is the opposite of my type. I always go for the kinda tattooed guy in a band (I know, I’m lame and typical as shit), and he is an extremely clean cut politician-in-training, with the button-up and ego to match. Nothing ever would’ve happened if we just met in a bar or something….

      4. bitter gay mark says:

        Oooooh, dang! Tattoos are so hot once one nears 40 and the start to stretch and sag… Ugh. I guess I am showing my age, but the whole tattoo thing is just tired and cliched to the max… Right up there with those jumbo cork like earrings I see far too many dudes sporting these days…

      5. Haha my sexual taste is definitely a cliche. I always go for the former skinny skateboarder with a sleeve that I meet at an indie show…its cool, I’m still young, I can change my mind later 🙂

      6. spaceboy761 says:

        It’s a little known fact that the simple act of uttering the last nine words of your reply karmically dooms to sobbing your 30 year-old eyes out and screaming “WHY AM I ALONE?!!!” while stuffing your face with eclairs from the Viennese table and wearing your fifth tacky bridesmaid’s dress in three years in front of all of your friends,

      7. Haa, I’m not one of those girls that is terrified of the prospect of being single. I don’t even want to get married. Also, I don’t like sweets, and my friends have very good taste!

  15. Quakergirl says:

    LW, I would advise you to make a decision assuming you’re going to have to leave your job. And not necessarily just leave, but leave without a reference or the ability to find another job quickly. The best case scenario is that you and your boss do manage to make your relationship work and you can continue working together without changing the office dynamic (possible, but unlikely). The worst case scenario is that you are fired or forced to leave amidst all the anger/hurt feelings/spitefulness of a breakup. Don’t underestimate how ugly this could get, and how long it might take you to find a new job, especially in this job market and especially if your boss says something negative about you in a reference check.

    And think how much pressure there’s going to be on this new relationship given all the possible consequences. If you stay at your job, that’s a) a lot of time together, and b) super complicated given the environment. And if you choose to leave, it probably will always floating in the back of your and your boss’s mind that you gave up your dream job for the relationship. That’s never a fun way to start a relationship. I’m not saying don’t do it, but just realize that you’re putting your job and the potential relationship at risk by starting things up while he’s still your boss.

    In the meantime, try to take your mind off him by keeping busy, going out with friends, or even casually flirting with or dating a few people. Obviously don’t lead anyone on while you’re still hung up on your boss, but a few flirtatious exchanges or a casual date may show you what’s still out there.

  16. Addie Pray says:

    I liked Wendy’s advice about talking to him about it… I’d be hesitant to make a move on your boss. I made out with a coworker in a conference room once. It was hot. I recommend it (with a coworker). That’s all I wanted to say.

    1. Hahaha I’m jealous.

      1. Addie Pray says:

        The only bad thing is the room had those automatic florescent lights that would flash on every time there was motion…. Lights can be a bad thing. 🙂

      2. I have an extremely innocent crush on a guy I loosely work with. Sometimes when I’m bored I fantasize about the proximity of us and the conference room. Hahahaha.

  17. I dated my boss once – it worked out quite well actually.

    Nevertheless, it was sometimes awkward at the office to try and maintain a professional relationship when we both just wanted to go do it on the conference table or something. Also, we worked with about 50 other people. I can’t imagine trying to make something like this work with a 3 person office.

    I didn’t read all the comments but my thoughts are that it’s simply not worth it. Your time would be better spent finding someone else to occupy your thoughts and your bed, and wipe this guy out of your mind all together. The only way I really see this working is if you went to work somewhere else… but finding a job you love so much would be challenging at best.

  18. silver_dragon_girl says:

    Ok, not to downplay your emotions here, but I’ve had a work crush at EVERY job I’ve ever had. And every time I convince myself that we’re soul mates and meant to be together. Has it ever once worked out? NO.

    I understand that the intensity of your feelings is impossible to ignore, but I really think that if you weren’t spending all day with this guy all the time things wouldn’t be this bad. I say use the work crush as a distraction when things get boring, and spend time outside of work looking for a boyfriend. You need a distraction from this guy- someone else to think about.

    Not to mention if you’re gettin’ some outside of work you won’t be thinking about it quite so much *at* work…

  19. LW- I could have written your letter a year ago. And I now have an incredible relationship because of it. BUT. The big difference between me and you is that my job was temporary from the beginning, and I didn’t take it too seriously as a job. It was just a two month thing to make some Summer pocket change. Fortunately, we had the opportunity and ability to just wait until the job was over before making any serious moves. And honestly, I believe that working together or going to school together are perfect ways to fall in love, because you don’t have that unnatural, forced pressure of dating while you’re getting to know each other.

    All that said, you’ve got to think long and hard about what you’re putting on the line here. You seem to really enjoy you’re job, as a long term thing. Is it worth losing? Would you be willing to work somewhere else if you guys broke up and/or if that was better for your relationship? Lots of questions to ask yourself…

    Good luck!

    1. SpyGlassez says:

      “I could have written your letter a year ago. And I now have an incredible relationship because of it. BUT. The big difference between me and you is that my job was temporary from the beginning, and I didn’t take it too seriously as a job. ”

      Likewise, except in my case it wasn’t a coworker but a student of mine at a community college where I’m an adjunct. We’ve been together for over 17 months now. However, we were only in the teacher-student relationship for 8 weeks (it was an accelerated composition class) and did not pursue anything until a couple weeks after classes ended. The main reason it has worked so well is that, while we met there, I would never have to have him in class again. I don’t know how it would have worked if we were in that kind of subordinate relationship every day, and trying to have a relationship outside of it.

  20. fallonthecity says:

    It’s a tough one, LW, but try to keep perspective. I have never seen an office romance work out where both parties kept their current jobs. They’ve either transferred to another department or left the job, whether the relationship worked out or not.

    If you do try to pursue this, try to keep it extremely professional for the sake of the other employee and for the sake of any customers or other people you work with. But I think you have to be prepared to choose between the guy and the job. And for me at least… it wouldn’t be even close to worth it. Then again, relationships are not exactly high on my priority list at this point in my life 🙂

  21. As my dad always said, don’t crap where you eat

    1. SpyGlassez says:

      Mine used a stronger word than crap, and put “sleep” in place of “eat.” But yea, good sentiment!

  22. Quickest way to diffuse this would be to be like, “Hey boss, you’re not going to believe what my friend did. She works with 2 other people and she went for the boss! Can you believe it? How awkward would that be! What an idiot!”

  23. I’m living proof you can date your boss and almost live happily ever after. I was enlisted and dated an officer while in the service. I approached him, I don’t think he ever paid much attention to me, he treated everyone regardless of rank equally and that so impressed me, of course he was very handsome. He was killed some time ago but we got married and had a family first. Life is short, take chances even just a few moments, a few breaths with him were worth it, it was wonderful love. However in order for us to make it work I did get out of the military when it was time!

    1. That is the most awe inspiring reply! I will take your advice as I am in the same situation as you were and the LW is. Hugs xxxxx

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