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Q: An older married man at work started flirting with me, and when I refused to send him a selfie, things got awkward. What could I have done differently?

I am a woman in my mid-20s, who started at a company a few months ago and took a very junior position. A mid-40s married male colleague in a leadership role was very kind to me, and I felt he really facilitated my integration into the company. Soon we were talking frequently in the mornings before work at the company gym, and also during his breaks.

I enjoyed talking to him, but due to our difference in positions he had to initiate most of our conversations. He'd come by my desk a few times a day and chat with me for five minutes. He told me that he was unhappy with his job and hinted that he was unhappy in his marriage. Since I was new to the area, I was very lonely and talking to him was the highlight of my day.

One day after work, he told me that he wanted to take me to a place. We drove to a park, and he told me that we were talking too much at work, and people would suspect that we were having an affair. And he said that if I wanted to talk to him, we could arrange to meet in a park. He said we might lose our jobs.

He then went away on a business trip/ vacation and while he was gone, he started texting me. At first, it was innocent enough and regarded work stuff, but then he asked me for a selfie. Thinking it was a bad joke, I sent him a picture of a cat. But he continued to pressure me to send him a photo, and when I stopped responding, he said something to the effect of, “I see that you’re busy and I’ll stop bothering you now.”

After that, working in the same office with him was very uncomfortable. He has since moved onto another company, but he made me feel extremely uncomfortable and vulnerable. Was I overreacting? What should I have done?

A: An emotional affair is basically an affair without the physical component and would imply that you had feelings for this guy. It doesn’t sound to me like you did. Rather, it sounds like this dude was being incredibly inappropriate and skeevy toward you. (Which makes me think your friends are being weird in labeling this an emotional affair rather than something more one-sided.)

It’s not that an older married man can never have a friendship with a younger woman, but genuine friendship doesn’t come with attempts at secret assignations in the park and intrusive questions, and it doesn’t leave one of the parties feeling “extremely uncomfortable and vulnerable.”

This dude was at a minimum attempting to carry on a secret flirtation with you, and he was almost certainly interested in more. His conduct with you was pretty much a walking red flag:

  • Telling you that he was unhappy in his marriage: red flag
  • Asking you to send him a photo: red flag (Do your platonic friends nag you for selfies? Do your coworkers? That’s pretty much the province of people with non-platonic interest.)
  • Telling you that your relationship needed to be on the down-low: huge red flag
  • Saying you could lose your jobs: red flag (For what? Office friendships don’t generally jeopardize people’s jobs; he had something else in mind.)

And the biggest red flags of all: making you feel that any tension would be seen as your fault rather than his (which is a really convenient side effect when someone with more power hits on someone with less power), and making you feel trapped in a situation that you weren’t comfortable with.

So I’m pretty comfortable concluding that he was a skeevy dude taking advantage of a professional power dynamic that — intentionally or not — made it easier for him to get away with making you uncomfortable because you were hesitant to call him out.

I wouldn’t call that an emotional affair. I’d call it unwelcome and inappropriate conduct and possibly harassment.

You asked what you should have done. First, let me say that no one tells you how to handle this stuff, so you shouldn’t beat yourself up for anything you did or didn’t do. You tried to be friendly to someone who you thought was being genuinely friendly to you. You’re not responsible for him crossing lines with you or for not perfectly shutting it down when he did.

But in the future if someone’s behavior starts making you uncomfortable (which in this case sounds like it might have been the day of the trip to the park), ideally you’d be clear that you need the person to back off. How you do that is up to you and depends on what you’re comfortable with. Some people are most comfortable doing that by pulling way back on the social relationship and keeping the interactions strictly professional in order to give the other person a cue in a way that lets the other person save some face. (However, some people will respect that cue and some won’t.) Other people prefer to directly tell the person that they’re not interested and the behavior is unwelcome (which can range from “I’m really not interested in meeting you outside of work” to “I’m not comfortable with this conversation” to “please leave me alone”).

If the person doesn’t back off after you’ve directly told them that their behavior is unwelcome, at that point you have a potential harassment situation and you should talk to your manager or HR or someone in a position of authority in your company who you feel comfortable approaching. No healthy company would blame you for the situation if they heard about the fact that you’d asked him to stop and he hadn’t. That’s pretty much textbook harassment and most companies take it seriously.

I’d say that the best thing you can do here is to see this situation for what it was: not an emotional affair, not you being responsible for any potential tension, but an older married colleague getting you comfortable with him and then coming on to you in a way you found unwelcome. That reflects on him, not on you.

Q: What can I do about my coworker’s girlfriend constantly hanging out in his office?

My coworker's girlfriend drops by for plausible reasons like lunch or for his birthday, but she stays too long. Today she stayed for 1.5 hours. They kept the door to his office open. At one point they were going over flashcards for her schoolwork. This was from 3:00-4:30.

I am not his direct supervisor, but I am above him in title and supervise others in the office. We work for admissions at a university and while accepted students are protected by law I don’t believe prospects are. Still, we discuss transcripts and items with personal info that a non-employee shouldn’t see.

Our supervisor is the type who avoids any kind of conflict and doesn’t address people-stuff head on. The culture is somewhat relaxed. I am wondering if it’s even worth mentioning.

A: Yeah, that’s ridiculous. Hanging around his office for an hour and a half? Doing flashcards for her schoolwork? It’s unprofessional and it doesn’t reflect well on his work ethic; that’s a lot of time for him not to be working. I’m more concerned about that than I am about her seeing students’ information, although that’s a concern too.

This is really for his manager to deal with, but if you have the kind of seniority where you could give him a pointed, concerned look as you pass his office, I’m grinch-like enough to do that.

These questions are adapted from ones that originally appeared on Ask a Manager. Some questions have been edited for length.

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