I know a lot about one of my boyfriend’s friends’ past relationships. I’m not particularly close to her one-on-one. Should I just say something or stay out of it?

How to Do It is Slate 's sex advice column from Stoya and Rich .

Stoya offers advice on how to protect someone younger from getting her feelings hurt or self-image obstructed by an alleged patriarchal dickhead.

For the sake of maintaining peace within the friend group, tread lightly.

If you want to help her, do it right.

I would say I am a good-looking, in-shape, older guy. Other people have remarked that I am handsome, stylish, smart, smart.

I usually get something like, “Oh, you look nice.” Should that be enough? Maybe, "You look nice" is the best he can do verbally.

Maybe the move here is not to interpret feedback from others as a sign of what your partner is lacking.

A divorced woman has not dated or had sex in nearly 10 years .

She realized that she always chose men who needed help so she wouldn’t have to focus on her own issues.

She resolved her lifetime fear of ending up alone and realized that being single was kind of excellent, actually.