Ask Him: Break the Glass Ceiling? I’m Banging My Boss!

Q: “You should never go to Nashville on a business trip with your boss, because you might end up sleeping with him. That’s what happened to me, and it has continued for the past month or so. I think he’s falling in love with me, and I like him a lot too, but I’m also really scared that it will go wrong. I think it could hurt my career. What should I do?”

having sex with boss

A: Ah, yes, the timeless question of what in the hell you’re supposed to do after you f**k a co-worker despite the fact you told yourself you would never, ever, do something like that. Because there is a certain level of taboo to dipping the pen in the company ink. I’ve been there, but not with a superior. And it was also after I had turned in my two weeks’ notice and was poised to move hundreds of miles away. So my situation was much more carefree than yours. I still miss this girl sometimes. She was very good at sex things.

First, try not to freak out about this. There is absolutely no way that it should be able to negatively affect your career. It actually shouldn’t affect your career at all, in any way, but more on that later. And it’s not at all uncommon to be attracted to people you work with, and to act on that attraction at some point. These are the people you’re spending most of your time with if you’re single. And the people you probably dress your nicest around.

Sometimes, like with any relationship, things go to sh*t, which can result in, at the very least, awkwardness in the office (though I know plenty of people who have gotten past this and are now fine working together and are also friends).

But occasionally, they work out very well. The Office‘s Jim and Pam storyline isn’t just an aspirational fiction. I work with a dude who worked the same job with his wife for many years. They would commute together and work on the same floor, doing the same things for different clients. And he loved it. I also used to work with a married couple who sat right across from each other. That’s a whole lot of together time, but it also means that you have a really good source of support at work. And someone you can sneak away with for nooners and stuff. That would be really cool.

The fact that he’s your boss kind of throws a number of cogs into the machine that could potentially produce a whole lot of chaos. Guys can be real pricks after the end of a relationship, and I totally understand your fear that he could negatively affect your career. He could try and make things hell for you at your current job, and then if you leave he can become a really, really bad reference.

First thing I would do is make sure that all of your correspondence is saved and backed up. Use the cloud and an external hard drive or whatever you need to. If, god forbid, something happens where you have to let people know that you feel you might be being treated badly because of a non work-related romantic relationship, you’re going to have to have some kind of proof. (Be careful, though, that it really is because of the relationship, and not because you’re doing a terrible job work-wise.)

You also need to have conversations with your boss/lover about the situation. Often, we tend to put these sorts of conversations off, but this situation warrants an immediate conversation. You need to tell him your concerns and he needs to assure you that they’re unfounded. You need to lay out the ground rules for your relationship, which I would suggest keeping out of the workplace, at least at the beginning. I would agree not to tell co-workers, because people will immediately jump to the conclusion that you’re going to get preferential treatment because you’re snogging the boss. Nothing you do will be perceived as great — it will instead be perceived as decent but lauded by the boss because, you know, you’re hypnotizing him with your feminine charms or whatever.

Finally, make it clear that you don’t want or expect to be treated differently, and that you need to keep work completely separated from the relationship.

Except, of course, when you duck out for nooners.

Good luck. Make sure you both read up on the company’s HR rules for inter-office relationships.

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