Q: My best friend is dating a jerk and she doesn’t seem to see it. Every time I’ve hung out with them he has some snarky, sarcastic comment to say to her. He tries to disguise it as a joke but it’s clear to everyone (except my friend) that he’s simply being an ass.  Normally, I’d have no problem telling her how I feel. But I haven’t because before she started dating him, I had hooked up with him once and I don’t want her to think I’m just being resentful. I’m really not because I have no desire to be with him, but I also have no desire to see my friend be with such a mean guy.

A: Ok, I’m not going to get into why of ALL the men in NY, your friend had to date one that you were previously involved with. Clearly, the two of you have come to some sort of resolution on that issue so I’ll leave it alone.  So because of this “resolution”, it sounds like you have the type of friendship that can withstand constructive criticism (and I’m taking your word for it that it is truly constructive and not some residual bitterness). I say just tell her. Say that you feel uncomfortable hanging out with them because of the way he speaks to her. Make it all about her feelings and not about him as a person. Just remind her that you care and you don’t want her to feel belittled or disrespected. If she continues to be in denial, let it go. You’ve done your part as a friend. Another option: stop hanging out with them together. It’s a subtle way to take a stand.