ask a boss

‘My Boss Is Having Sex in the Office!’

Photo: Stanley Kubrick/Getty Images

Dear Boss, 

My first job out of college started as a dream: a hip tech startup in Los Angeles with a majority female team and an express mission of empowering women on social media. Now that I’ve been here almost a year, the cracks are starting to show, specifically with my boss. She’s C-level, and the “female face” of our company to investors, clients, etc., and while she pitches the company as empowerment-based, she’s anything but empowering to her employees and has put us all in a very uncomfortable situation.

She frequently cheats on her live-in boyfriend with other men in the office at night, often leaving evidence for us to discover in the morning. Just last week she started making out with several men in front of my co-worker while repping our company at a networking event. Everyone in the office knows, but I feel especially guilty because her boyfriend has my role in another company and has served as a mentor-esque figure for me in the past. 

Maybe this is just my Catholic guilt showing, but the whole situation makes me very uncomfortable. I can hardly stand to look at her, let alone her boyfriend. Knowing all of this information about her has made it hard to take her seriously as my boss and be comfortable and successful in the office. She plays it off like this is normal behavior in tech and that I would totally get it if I were older and more experienced, but if that’s the case, maybe I need to be in another industry. 

Do I need to quit my job? Do I tell her boyfriend? Is this normal and I’m just totally overreacting? Any advice would be greatly appreciated so my sleep schedule can return to semi-normalcy. 

Nope, this is not normal! Not in tech and not anywhere else. Certainly there are people in every industry who cheat on their significant others, but they don’t typically let their entire office know about it. And if they’re having sex in their office, they’re at least generally more discreet. (And leaving evidence behind?! I don’t even want to speculate on what that means.)

Normally, of course, your boss’s sex life and relationship choices would be none of your business. And if you’d stumbled on this information accidentally, I’d tell you to try to wipe it from your mind and pretend you didn’t know. I’d also point out that there might be context you weren’t aware of, like that her relationship was an open one. And who knows, maybe that’s the case here.

But it’s hard to consider this none of your business when your boss keeps making it your business by being so flagrant about it. It’s hard not to notice when your boss is making out with multiple people at a business event. And it’s even harder to ignore when she’s talking about it so openly.

The thing that matters here is: this stuff just doesn’t belong at work. Even if your boss is in an ethical non-monogamous relationship where all parties involved are fully informed and consenting, she’s making her sexual choices a focus of your workplace in a way that’s 100 percent inappropriate. In fact, even if she were single — and thus you weren’t worried about the cheating aspect of this — it would still be inappropriate for her colleagues to know this much about her sex life (let alone that some of that sex is apparently happening in the building where you work).

You just can’t inflict that on people at work. And you especially can’t inflict it on people who work for you, since the power dynamics of boss/employee relationships mean that people may feel uncomfortable and unable to speak up and say “Hey, I don’t want to hear about this.”

That said … it’s worth thinking about whether gender is playing into how you and others perceive this. To be clear, this behavior would be inappropriate from anyone, man or woman — but sometimes women are condemned more strongly for it than men would be. Some of that is rooted in old sexist tropes, of course. But sometimes there’s another thing at play, too: Sometimes we unfairly expect the female leaders in our offices to be perfect models of professionalism and to meet a standard that we don’t hold their male counterparts to, because at some level we figure that if they’re perfectly polished and appropriate and skilled, the path will be eased for other women. In other words, we expect senior professional women to represent all women in a way that we don’t expect men to — and that’s an unfair burden to place on women (particularly on top of other burdens of sexism they’re already shouldering).

That’s not to say your boss isn’t being wildly inappropriate. She is! But be sure you’re using a gender-neutral lens when you think about her behavior, and take a hard look at any feelings you might have about how she’s representing women in general in your office. (If you have them, that is. Maybe you don’t! But it’s common enough that it’s worth flagging.)

As for what you should actually do here … What do you want to do? Given the power dynamics at play, it’s okay to discard any worries about what you might or might not be obligated to do and just focus on what you’re comfortable with.

That’s particularly true when it comes to telling her boyfriend what’s going on. Certainly if you feel ethically compelled to do that, you can — but you’re not obligated to, and you’re not a bad person if you choose not to. This is your boss, and presumably you could jeopardize your job if you out her to her boyfriend. You are not required to jeopardize your livelihood in an effort to make this right.

That doesn’t mean, though, that there aren’t other things you can do. You’re absolutely allowed to say to your boss, “This makes me uncomfortable to hear about, especially since I know Ryan. I would rather not hear this kind of thing!” She may think you’re being overly delicate, but you can make this request and stick to it.

You also asked if you need to quit your job. The answer to that is: Only if you want to. You might decide that you have so little respect for your boundary-violating boss that it does make sense to move on. Or you might decide that, while gross, the situation doesn’t rise to that level.

But you’re not overreacting, and you don’t need to worry that you’ll encounter this issue at all future jobs. This is just one weird boss out of control, not a corporate trend or a staple of work life.

Order Alison Green’s book, Ask a Manager: Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Work, here. Got a question for her? Email Her advice column appears here every Tuesday.

‘My Boss Is Having Sex in the Office!’