Here’s how most people tell you to deal with a crush on your boss: don’t. They say that all the drama from the relationship can be bad for both your career and his, so your best bet is to let it go. However, sometimes the heart just wants what it wants. So if you’ve fallen hard for your boss, this advice is for you.
If you must tell your coworkers…
Telling your coworkers about your office crush is a bad idea. Your best friend at work may find it too tempting to keep from spilling the beans to just one other person—who can’t keep a secret. Tell someone you work closely with, and they could see it as juicy gossip. If you must tell someone at work, tell a friend who doesn’t work in the same department you do. Choose someone who’s removed from the situation, doesn’t know everyone involved, and wouldn’t feel like she’s keeping a big secret if you confide in her.
If you must flirt with him…
If you and your boss have a flirtatious relationship, it can make work more interesting. It could even be a productivity enhancement. But it’s important to flirt smartly, because your co-workers will notice these things. It could make you seem less professional to some of them.
Don’t flirt in front of other employees. Consider what might make coworkers uncomfortable if they saw or overheard you; don’t touch, and go easy on the innuendo. If he’s not responding to your flirtation in kind, it’s probably because he isn’t interested—not because he’s shy.
If you must know whether he’s flirting back…
If you have an unreciprocated crush, that’s one thing; if he flirts with you, it can be even more exciting and interesting to deal with.
But just because he’s flirting with you doesn’t necessarily mean he’s as interested as you are. It could be because your attention feeds his ego and makes him feel good. To find out, withdraw from your regular behavior for a few days and watch his reaction carefully. If he just shrugs and withdraws in kind, chances are he didn’t attach much meaning to your interaction.
If you must ask him out…
If you absolutely must ask your boss out, it’s better to do it away from the office, in a situation where you’re more likely to be acting as peers, not boss-and-employee. Make it clear that you don’t want this to affect your working relationship, no matter what.
If you’re going to admit your feelings at all…
Confessing your feelings to your boss or even openly flirting is risky. If he’s not comfortable with the attention, you could be wading into the waters of sexual harassment. If you tell him how you feel, it could lead to a great relationship—or it could make him think you’re likely to bring up a sexual harassment suit against him, even if that’s the furthest thing from your mind.
Be aware that there will be consequences—either positive or negative—that could affect your job—the least likely outcome is that nothing will change. Handle this situation with care, and be discreet about it at the office—and hopefully you’ll wind up with a wonderful new relationship, not a disaster.
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Another thing I’d like to add: be prepared to find a new job if your relationship progresses. I got into a relationship with, while not my direct boss, the 2nd in command of my small (20 person) office. We kept it very discreet, but as our relationship progressed it got increasingly difficult to keep it a secret and also to worry about people seeing us together, etc.
I had a good job there and could have gone places, career-wise there, but it became clear that our relationship was going somewhere more than casual dating. I found a new job and we eventually got married.
A job’s a job and I’d advise before getting involved with someone at work you evaluate whether, if this guy/gal turns out to be your soulmate, are you willing to go get a new job? If you just can’t imagine having to give up the job, I wouldn’t even think about dating anyone at work. It’s just a recipe for disaster–either you break up and it’s uncomfortable or you end up being totally in love but always having to look over your shoulder, feeling like you’re sneaking around.
Either get over the crush or follow the above advice.
I cannot really see anything positive for one’s professional life by hooking up with the boss.
The boss?
This is a well written post. However I would add if it looks like a relationship in the making to have a backup plan (i.e. - another job lined up). Maybe the ‘boss’ could arrange for a transfer. While I was reading this post I felt like I was walking on eggshells as it went from a crush to flirting to asking him/her out on a date to a relationship.
What happens when it comes time to do a performance review? This is when who you know really comes into play.
[…] totally normal to have a crush on someone at work. And it is totally normal for people to tell you not to act on it. And it is totally normal to throw caution to the wind. According to Helaine Olen, author of the […]