My friend has a cheating problem. She's cheated on every boyfriend she's had. Until recently, she told me about many of these conquests. However, I've always been disapproving - urging her to end these affairs, or break up with the current boyfriend.

So she's become more withholding. She just ended a yearlong relationship with a boyfriend who's a good friend of mine.
To my knowledge, she'd slept with four other guys while committed to my friend. They're now broken up because of "trust" issues (he knew about one of these men). I don't want to hurt him with the knowledge of the others, but I also want to urge him to be tested for STDs, as I've known her to have unprotected sex in the past.

How do I do this without all of the above blowing up in my face, and hurting everyone involved?

In the Middle

Protect the guy by advising him to get tested. You don't need to list all her other affairs, he already knows about one of the men and it only takes one to be exposed to an STD.

Then bow out of this messy friendship. You don't approve of her behaviour, it's demeaning for you to be a confidante, and you don't have much respect for her judgement anyway, so there's not much left for friendship other than the gossipy position of knowing too much.

This won't "blow up in your face" if you simply encourage the guy, and stay distant from the woman.

Last December we went out for breakfast, and my daughter and her family came in. When my daughter sat next to my husband, her stepfather, he said his day was ruined. She and I felt this was really rude but didn't say anything. At Christmas, she said she couldn't give him a gift, as he'd really upset her. So that day, he left to visit friends, returned late, went to the basement and wouldn't talk to us, stating that he'd already eaten.

I was hurt; he ruined Christmas for me. But he sees nothing wrong with his behaviour. Was I upset over nothing?

Upset

There's tension between those two that needs working out. Urge them both to deal with this, or there'll be more incidents, more hurts all around.

FEEDBACK Here's a view of one woman's reaction to strip clubs (Feb. 24). Also see March 23 for a related question and answer:

Reader - "The wife's disapproval of strip clubs may come from any number of things, including her own body image or perhaps past indiscretions.

"She expressed her displeasure with her husband's frequent visits to strip clubs, not banished it all together. By laughing it off, he doesn't show respect for her. His continued visits and lack of openness about those outings make it cheating. That is a breach of trust and she should not "loosen the reigns" - it might serve as a free pass to him.

"There are plenty of other places where guys can hang out that do not involve giving money to someone who is taking off their clothes.

"Maybe he should try cutting back or even share the excitement of it with her. Inviting her to either go with him to see what it's like or maybe asking her to put on a show just for him. This could be a great intimacy booster for them.

"Yes, I agree with you that counselling could be beneficial in dealing with her insecurities and his secretiveness."

FEEDBACK Regarding the girl, 15, who's troubled after parties (February 21):

Reader - "She needs to look at who she hangs out with and whether they're the right friends for her. We went through the same thing with our daughter, at 15.

"Within six months, she changed her entire group of friends. She was still friendly with the old ones, but stopped hanging out with them on weekend nights. She just wasn't comfortable with their choices and wanted to make choices she knew were right.
"She started hanging out more with the girls on her cross country and track teams who were committed to their sport. She got involved in a nondenominational religious organization that had a chapter specifically for teens attending her school. She met kids from other local schools when they would hold regional meetings. She's now in college and leading a group at a high school nearby."