What About Just A Hook-Up With My Boss?

A question to Ask the Workplace Doctors about sex with the boss.

Question: I really like my boss, but I just want a hook up. No dating, no relationship, no commitments, nothing like that.

Answer: We’re a site about workplace communication issues, rather than an advice column about romance and/or sexual activity. However, you may benefit from a reasonable and practical response to your question.

A fact of life is that men and women together are the basic ingredients for sexual interest. Add to that the shared problems, frustrations and achievements of a workplace and the interest can grow. A component for most people is the influence and work status of the other person, which can add to the intrigue and also has an affect on every element of that person’s appearance and demeanor. Put it all together and it’s not surprising there are so many sexual relationships (casual or serious) at work–and that the most common is a woman involved with a man of higher organizational level. There’s an entire genre of romantic fiction with variations on the theme!

When you consider the reasons you would like to hook-up with your boss (which will include at least some of the reasons above) you can see that it’s highly unlikely you could do it as you describe. It’s a nice fantasy scenario, but it’s just not the way it would work out.

For one thing, if you know your boss well enough to like him and enjoy being around him, you already have a relationship with him–apparently a good one. So, the first thing to consider is whether or not you are likely to be able to keep that same relationship if you let your boss know you are interested in unemotional, just-for-fun sex. Probably not.

The fact that you even mention the subject of sex will change everything, because it can’t be unsaid and it will be in the back of your minds after that. If you let him know you’re only interested in sex, he may figure you have said the same thing to who-knows-how-many-others and may be offended or shocked or feel sorry for you. It will change the dynamic of your work relationship dramatically.

Or, if he’s been around the block a few times, he may not believe you. A guy once told me cynically, “She said the same old thing they all say about, ‘I just want sex, not a relationship’. Yeah, right, no relationship until after we’re done having sex once, then she’ll cuddle up and tell me she never expected it to be so special.”

If he’s flattered but says no, there will still be a change. If he says yes, you have no assurance that he will not view it in a more serious way than you do. And, you have no assurance that you will be able to stay as pragmatic as you say you are.

You may also find that having sex with your boss turns out to be a disappointing experience or even unpleasant. Or, he might feel that way about you. When one or both of you realize you don’t really want to go to the trouble of doing it again, it can be very embarrassing to see each other at work and be required to carefully avoid having a repeat mentioned.

The result of changing your relationship from what it is now, will be that instead of having a good place to work, with a boss you like, you’ll be distracted, uncomfortable and stressful and probably you’ll wish you had left it the way it was. Even if you are able to have occasional sex sessions without romance or commitment, you’ll have to work out ways to set things up, find a place to do it, not be discovered at work and if either of you are married, not be discovered at home. It’s an incredibly complicated situation that takes a lot of the fun out of the activity.

There is also the consideration that if you are in an organization beyond a one or two person business, there will be rules or policies about relationships or sexual activity between a boss and a subordinate employee. If there is a rule against it, you could both be fired if anyone finds out–which nearly always is what happens.

Further, if your boss isn’t interested in that kind of situation or even if he is, he might report you for even suggesting it to him. He might not want to report you, but might fear repercussions if he doesn’t or fears allegations by you one of these days.

If you decide to find a job somewhere else or if you are no longer working around each other in the way you are now, that would change the situation. Then, you could contact him and be more open about your attraction for him and what you’d like to do about it.

You could try a slightly flirtatious suggestion, but a blatant statement would be more effective and would get you a yes or no. “I couldn’t say this while we were working together, but I can now. I don’t want to get involved with a romance or commitments or phone calls or daily texts or things like that, I just would like to get together with you in some place private now and then for whatever develops. What are the chances that can happen?”

He’ll get the message and can let you know if he’s agreeable to that kind of no-strings-attached activity. Remember though, that you can’t control his feelings or even your own. So, if you don’t want to risk something that may be difficult to stop, make sure you’re in a situation where you can stay completely away from him when it’s over.

After all of that, I would be remiss if I didn’t remind you that at any age and in any circumstance, you should put your focus on making decisions that will move you forward in the life you want to have five years, ten years and many more years from now.

Part of maturing is learning lessons from bad decisions. Sadly, some of those decisions that mature us are because we have suffered (or caused others to suffer) a lot of mental, emotional or physical pain. I hope you will be conscious about decision points in your life and back away from those that you know have a high likelihood of causing you regret, while enjoying the good feeling of choosing the things that are most likely to bring happiness, mental peace and a clear conscience.

Best wishes to you!
Tina Lewis Rowe
Ask the Workplace Doctors

Tina Lewis Rowe

Tina had a thirty-three year career in law enforcement, serving with the Denver Police Department from 1969-1994 and was the Presidential United States Marshal for Colorado from 1994-2002. She provides training to law enforcement organizations and private sector groups and does conference presentations related to leadership, workplace communications and customized topics. Her style is inspirational with humor.