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.
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, new 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.