Dear Carolyn • I (female) have a very good friend (male). He's a great guy and we really enjoy each other's company. I do know, through conversations with him, that he's pretty much a jerk to women he dates/sleeps with, but our friendship doesn't revolve around this, so I don't really care. I have another friend (female) who was interested in him. I told her that while he's a good friend I think he'd be a lousy boyfriend, and gave some specific examples. She claimed he'd be different with her and I stayed out of it, already having said my piece. Well, six months later, he was a jerk to her, too, and she's mad at me not him for not stopping her, and insists I can no longer be friends with him. How do I deal with this? I would really like to keep both friends.
Dear Messenger • That's not up to you, unfortunately. What you can do is take or leave the terms she's offering, and then she can decide whether to take or leave the friendship. I do think you have a right to say that you didn't feel it was your place to stop her, only to warn her and then say nothing further, because that already takes you to the very edge of the told-you-so cliff. Even if there were more you could do without pushing the limits of sincerity, it would be worth asking yourself if you really want to prostrate yourself to keep a friend who feels she can dictate whom you keep and don't keep as a friend. That's about it for this part of the situation with your two friends, but what about the other part that you're friends with someone you know treats women badly? Have you said anything to your male friend, during these revealing conversations, to the effect that it sounds as if he is lousy to the women he dates? Seems to me that passes both the boundaries test and the test to be sure you're not enabling a jerk. I'm projecting a bit here, but your it-doesn't-hurt-me-so-I-don't-care stance on his lousy behavior verges on mercenary and it's a mere hop, skip and a logical jump from that to the fact that you have two friends who don't exactly stand out for their maturity, humility or grace.