“Should I Tell My Work Crush I Have Feelings for Him?”

I have an intense crush on the guy I work with — every time I see him I just want to get closer and spend more time with him. I don’t know how he feels as he hasn’t been anything other than coworker-friendly to me; but then again, I have been the same. I don’t want to ruin things and make the work environment awkward if he finds out I like him and he doesn’t like me back, especially since we pretty much always have the same shifts. But I like him so much! I don’t know what to do. How can I get him to notice me more? Or should I tell him how I feel? Or is it not worth jeopardizing our place right now? — Work Crush

You have to tread very carefully with work crushes and there are a few questions you can ask yourself to determine whether the risk of pursing a crush is worth it. First and foremost, do you know whether he’s in a relationship? If he is, do NOT pursue him. If things didn’t work out between you two either because he’s not interested or because a relationship between you failed, and working together proved too awkward or hostile as a result, could you change your shift, role, or job fairly easily and without too much negative effect on your finances and career trajectory? Finally, what is the company policy on dating in the work place?

If your answer to all of these questions still leaves a potential relationship with him open, I would try to arrange some recreational time with him outside of work, ideally within a group setting where you can get a better sense of his interest level without being too forward. Invite a few co-workers out for happy hour after work some day or organize a group activity, like bowling, where you can gravitate toward each other casually and assess mutual interest.

If, after feeling him out outside of work, you get more than “co-worker friendly” vibes, you might suggest something more one-on-one the next time and see what he says. I would NOT confess feelings without at least a few one-on-one hang-outs first or you really will jeopardize your comfort at work, if not your job altogether, for zero signs that your feelings are reciprocated.

If you decide not to pursue him but still can’t stop thinking about him and your crush is affecting your work and/or mental well-being, you may want to start looking for a new job or at least ask to change your shift so you are no longer working directly with him.

My ex and I have known each other 20 years and have been on-and-off for four years. We just decided to work on our relationship again, which is long-distance. But I’m not sure if I should even re-open this door again. His family is planning a birthday party for his brother in Florida and the whole family will be attending. However, he did not ask me if l wanted to go. This is not the first time he has not invited me to one of his family events. I’m really pissed off thinking we were trying to work on things, but I really feel as though this is not the case. I just don’t know anymore. — On and Off and On Again

Honestly, if after 20 years as friends, and four years as on-and-off romantic partners, you still don’t know where you stand with the guy and what his commitment level is to you, it’s time to move on. You’re already pissed off at him after recently deciding to work on things. You two clearly don’t have similar expectations of the relationship and don’t know how to communicate your respective expectations to each other, even after all these years.

There’s a reason you keep breaking up and it outweighs whatever reason you have for continuing to keep getting back together. In addition, research suggests that these types of on-and-off relationships negatively affect one’s mental health. And something tells me that if you thought about your history with this guy, you might agree with that argument.


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If you have a relationship/dating question I can help answer, you can send me your letters at wendy​(AT)​dearwendy.com.


  1. Ruby Tuesday says:

    LW 2: Don’t waste 20 more years on this man. If nothing’s changed in 20 years, what makes this time different?

    Nothing. Nothing at all.

  2. dinoceros says:

    LW1: I’m not sure how old you are, but after you get to a certain age, you don’t really “tell someone your feelings” if you barely know them. “I really like you, even though we’ve only ever interacted at work and as co-workers.” That would sound bonkers. It’s nice that you have an idea that he might be someone you might like outside of work, but at this point, you don’t know anything about who he is. (A lot of people are very different outside of work.) So, the next step would be to try to get to know him better by following Wendy’s advice.

    LW2: No, you should not try, but not for the reasons you mentioned. You guys have made your relationship so complicated that there’s no real yes-or-no on whether he should have invited you. You’re off, you’re on, who really knows? That’s the point though. Relationships where people are off and on, break up several times, don’t know where they stand, know each other for decades and still have never gotten anywhere — those are all signs you are not right for each other. Don’t waste more time trying to make this work.

  3. LW1, you sound young and maybe like this isn’t a career type job. In that case, for every scenario I think it makes sense to look for alternate employment arrangement, be it a different shift, a different department, or a different job. The options are: 1. Keep working with a dude you have a big crush on but don’t do anything about, 2. Make a move and then be working closely with your SO, or 3. Make a move and get shot down and then have to work with a guy who knows you like him and doesn’t like you back or 4. Date and break up, and then have to work with your ex.
    So if changing shifts or departments or even jobs is easy, then definitely do that before you make a move. If this is a more permanent/career type job and its not easy to change shifts or departments, then do nothing and wait for this crush to flame out.

  4. L2, I don’t agree that he should invite you to an attend a large (out of state?) family event. You’re off and on, and just recently decided to try again how does that make you stable and serious enough to bring to a family gathering? Let a lone a large one possibly out of state?

    I also don’t think you should decide to re start anything while you’re long distance. Long distance relationships can be difficult even with a solid foundation, which you don’t have. Work on yourself and once you’re both living in the same area that would be a time to reassess.

    1. Ugh the typos. Apparently i need more coffee.

    2. Bittergaymark says:

      Yeah. I whole heartedly agree. A family reunion / milestone birthday party fir somebody else is NOT where one begins to refocus on their on and off relationship again. I disagree with Wendy that this is some slight on his part and thus reveals his lack of interest.

  5. I agree with the last few posters and find it strange that LW would expect to go to this reunion. That has a strong whiff of desperation for instant relationship affirmation. After on-again, off-again and now only beginning to try yet again, there cannot possibly any instant determination whether it is going to magically work this time around. Most likely it won’t work, if you’ve broken up multiple times after knowing each other for a decade and a half, there likely is some major incompatibility in play. I suspect he has as much doubt about whether this time is the charm as you do and the last thing he wants to do is prompt a discussion with all his relatives “isn’t this the woman you were with before… and before that”… raised eyebrows, accompanied by sad, slightly pitying look. LW has to give this some time, before she has any expectations at all, or just decide that any chance at a relationship passed some time ago..

    1. dinoceros says:

      Yeah. As much as I assume the LW might not like to hear it, dating for 4 years off and on is not the same as dating for 4 years.

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