My sister is dating her boss

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Hi Meredith,

My sister has had a decently messy love life for many years. She's very insecure about herself, her relationships with others, the way she looks, etc., and it shows in her relationships. She's very kind, but she has commitment issues and will fling herself at any person who shows her a modicum of kindness or attention. She cycles through close friends and cheats on every person she dates. She's been in therapy for years and has discussed all of this with her therapist. We're very close and she trusts me to be honest with her about her decisions. I try not to be judgmental and let her work through her issues, only offering advice when asked.

Well, now she's dating her boss who is 15 years her senior. She's told me about how she's very open with her feelings and struggles at work, whether it comes to her strained relationship with her ex, our parents (she recently moved out of their house) or friends. I think it's inappropriate, but apparently it's very normal(?) at their office. This guy she is now seeing has three very young kids. She confessed her feelings to him while he was still married and seemingly had no intentions of getting a divorce. But in the few weeks since then, he has moved out, filed for divorce, and is fully dating my sister. He's 40! And she expressed in recent months, pre-relationship, that she doesn’t want children and felt pressured by our family to do so, yet now she’s weighing being a stepmother to these young kids.

Her company has a strict policy against superiors and subordinates dating, and I believe some coworkers have caught on. But she doesn't care because "we're in love." She could lose her job, a job she loves, over this. He even told her that if it came down to one of them being fired because of the relationship, she would likely be the one to get axed because she’s newer to the company. Seems like an awfully cavalier attitude to have about your partner's future. I've already expressed my concerns, which are 1) that I think he's a skeeze for actively pursuing a relationship with her in secret despite the stark power imbalance and the strong possibility she would lose her job; 2) that he has three kids, which she does not want, and that will inevitably become an issue and 3) that she's 25 and does not need to worry about settling down with somebody closer in age to our parents than her. She says I infantilize her by saying the age gap is an issue; I think he's just looking for somebody young, pretty and without objection so he can feel better about himself. I love her dearly and don’t want to see her lose what she’s built for a man having a midlife crisis. Apologies for the long letter, but how can I convince her to dump this guy?

– Meredith

You can't convince her to dump this guy. There's literally no way to do that. Sorry.

You've told her all the reasons you're concerned, and she's told you she doesn't care about those potential problems. All you can do now is set boundaries for yourself.

What boundaries? Well, if you feel like all she does is talk about this man, you can tell her you miss talking about work, her other interests, etc. I mean, that seems to be an issue here – that her romantic narratives have taken over your relationship (and ruined some friendships). It seems that whenever she dates someone, she drops everything and is all about that person. And in this case, yes, the person is her boss, and that is upsetting.

The biggest red flag, to me, is the work stuff. He's her superior and yeah, he's being pretty "oh well, whatever" about how this decision could affect her career path (based on what you’ve told us, at least). Also, he might be wrong about who gets fired for this. We’re (hopefully) at the point where companies have started to pin responsibility on managers – the people with the power. He might be surprised to learn that he's the guy who has to start looking for work.

Regardless, the other issues are too difficult to make guesses about. Maybe they are madly in love, and maybe she adores the kids. Who knows? Or maybe this will end like her other relationships, and this won't be a long-term worry.

You have to accept that you can't pull her out of this decision. You can only remind her about the rest of her life by asking questions, and be there for her in ways that are healthy for you.

I worked with the NPR's LifeKit on a podcast episode about how to give advice, and it might help. Especially point No. 2. Take a listen.

– Meredith

Readers? How do you sit back and watch this kind of relationship without trying to advise?