How To Sleep With Your Boss… and Survive

We’re going to be totally straight with you here: having a consensual sexual relationship with your boss is a win-win situation. Although we’ve all watched the sexual harassment videos, people get it on in the workplace all the time. If you sense the beginnings of a spark between you and your superior, here’s how to fan it into a flame and what to do when it’s over.

Your First Interview

If you suspect that there might be a little chemistry there, the most important thing is trying to set up some one-on-one time outside of the office so you can feel things out away from the prying eyes of your co-workers. If she’s interested, this should be easy. Most workplaces have a group of people who get together for drinks after work every so often, and life’s easier if your boss is one of them. If she’s not, invent a pretext for some after-work time – a project you’d like to discuss with her after working hours.

Make The Move

If she says that she can’t associate with employees outside of the office, that’s it. Game over. If she agrees, though, you’re in. This is the hardest part of the whole gambit: crossing the Rubicon from business associates to booty call buddies. Once you’re at your after-work rendezvous, open the conversation casually. Explore mutual interests, but scrupulously keep the chit-chat away from work issues.

Let Her Initiate

This is the biggest and most important secret to getting with your boss. They need to make the first move. So it’s your job to set up a situation in which that first move can occur. After your post-work liason, offer to walk her to her car. This opens up plenty of opportunities for increased physical intimacy. Most office romances start with spontaneous uncontrollable make-outs, so you need to create a space for one to happen. From there, it’s all good.

Don’t Expect Special Treatment

If you’re nailing your boss because you think it’s going to help you get ahead, you’re not alone – some 37% of office workers believe that sleeping your way to the top is a viable strategy, according to a recent survey conducted by the Center for World-Life Policy. We don’t recommend it though, because it makes everything weird. No matter how much of a wildcat you are in the sack, trying to trade it in for a raise opens ethical doors you want to keep closed.

Keep It Secret

The most important thing about an office romance is keeping it under the table. If your co-workers know about your liason, there’s all kinds of things they can do to make life difficult for you. And, let’s be honest, keeping it secret also makes it that much hotter. A hook-up with your boss is never going to develop into a long-term relationship, it’s just too weird. Once it’s over, it’s over.

End It Gracefully

There are a number of ways an office relationship can end. The good news is, just about all of them are good for you. If you’re dismissed from the company for some reason, you can make your relationship public and use it as a bargaining chip for more severance or other perks. If you break up with her, things might be awkward but she’ll be helpless to take her anger out on you for fear of you going to HR. If she breaks up with you, whatever: you’re no worse off than you were before, and hopefully you made copies of the keys to the supply cabinet.