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.
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