my coworker has a crush on our boss and is mad that I asked her to stop talking about him

A reader writes:

I work for a small company. We are an office of about 10 people and most of my colleagues have worked with each other for several years. My position was newly created to take some of the clerical burden off the others, and I’m definitely the new kid on the block, so to speak. Ive been there about four months now.

The problem I’m running into is our chatty office manager, Jan, who I work most closely with. Although Jan is a great technical worker, personally she driving me nuts. Through many conversations with her, it’s clear she has a crush on on our boss, Keith (10 years younger than her, 10 years older than me). Keith is a retired fire fighter and the textbook tall, dark, and handsome. He’s charismatic but professional. For context, Jan’s husband passed away suddenly about a year and a half before I started working there. I think the loneliness of being a widow is setting in and that’s why she had eyes for our boss, simply because he pays attention to her.

It has gotten to the point that whenever I’m alone with Jan, the conversation quickly turns to an unrelated conversation about Keith. Most of the time, I just ignore her or redirect the conversation to the original topic. This seemed to be working up until recently. Over lunch the other day, Jan and I were talking about a time-consuming project the office was working on for a client. Keith seemed irritated about possibly not meeting our deadline. Jan said, “I wonder what his wife does to make him relax at home, I know what I would do. Oh, who am I kidding, you would have a better chance with him since you’re younger.” I finally stopped her and said I didn’t feel comfortable talking about Keith in that manner with her, and frankly the continued conversations about him were getting annoying. Her response was, “Oh, it’s just a little girl talk. There’s no harm in that.” I countered with, “I’d rather talk about something else” and then changed the subject. I could tell I embarrassed her. We awkwardly finished our lunch and she was very curt and stand-off ish the rest of the day.

For the last week, if the conversation happens to drift towards Keith she’ll say, “Oh, that’s right, we can’t talk about about him” or if I have my office door shut (to avoid her!) she’ll proclaim to the office that I’m not being social today.

I’m not sure how to approach Jan going forward. Do I confront her and call out her immature behavior? Since we are such a small office and I’m fairly new, I really don’t feel like I have anyone I can confide in. Do I just keep ignoring her so she doesn’t get a reaction? I also don’t feel comfortable going to Keith just yet because I feel like it will just be an awkward she said-she said conversation. I feel like she’ll just gaslight me to make me look crazy to stay in his good graces.

First things first: You have the right not to be exposed to sexual comments at work, and you have the right not to be hassled when you express that sexual comments are unwelcome. If you want to escalate this, you can.

I’m guessing in such a small company you don’t have HR or even pseudo-HR, which makes this harder. But if Keith is the person you’d need to report it to, you can do that! You mentioned you’re worried it’ll be a she said/she said situation … but that’s true of most reports of sexual inappropriateness at work, and it’s still worth doing if you’re feeling harassed. It doesn’t sound like you’re necessarily at the point where you want to take that option, but it’s there if that changes.

If you don’t want to go that route, my advice is to keep ignoring Jan for a few weeks and then reassess.

If she says you’re not being social because you have your door closed, just ignore that or calmly say, “Yep, just trying to focus.” I’m not sure exactly what she’s trying to get out of you, but my best guess is that she wants you to walk back what you said so that she feels better about it. You don’t need to.

And when she says, “Oh, that’s right, we can’t talk about Keith,” you should take that as a win. She’s right, she can’t talk about Keith. If you want, you could respond very sincerely with, “Thanks, I appreciate you respecting that” … or you can just ignore her. She’s likely to get tired of making those comments eventually. Or someone will overhear and ask why she can’t talk about Keith, and the answer she’s likely to give will reflect poorly on her, not you.

If she’s still doing this a couple of weeks from now, or if she starts escalating how obnoxious she’s being, at that point it might be worth trying to clear the air by saying something like, “I think I embarrassed you when I asked you not to talk about Keith that way. That wasn’t my intention. I’m not comfortable hearing anyone we work with spoken about in a sexual way, even if you’re just joking around. I hope you understand.”

But if that doesn’t solve it, then you’ve got to decide how much she’s bothering you and weigh that against your desire not to bring Keith into it. To help overcome your discomfort about involving him: If a man you managed were talking about you this way and then freezing out someone who objected, wouldn’t you want to know? I’m not always a fan of flipping the genders as a thought experiment unless you can also reverse thousands of years of history and systemic sexism, but in this case it might help you feel more comfortable letting him know.

But let’s hope that after a few weeks of not getting a rise from you with her comments, Jan will pull herself together and move on.