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Tell Me About It: Friend is a jerk to his dates

Adapted from a recent online discussion. Question: I (female) have a very good friend (male). He's great and we enjoy each other's company.

Adapted from a recent online discussion.

Question: I (female) have a very good friend (male). He's great and we 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 examples. She claimed he'd be different with her and I stayed out of it.

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 like to keep both friends.

Answer: What you can do is take or leave the terms she's offering, then she can decide whether to take or leave the friendship.

I 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.

That's about it for this situation with your friends, but what about the other thing - that you're friends with someone you know treats women badly? Have you said anything to him, during those conversations, to the effect that it sounds as if he's lousy to women he dates?

Seems to me that passes both the boundaries test and the test to be sure you're not enabling a jerk. 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.