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Is it OK to date your friend's ex?

Q. A friend forwarded to me the online-dating profile of a former boyfriend of mine, and asked if that was him. She said they had spoken on the phone and were to meet in person. Apparently she was trying to feel out what I thought about it.

I said I couldn't tell her what to do, but I'm sure she knew I was upset.

I would never do that to a friend, and I feel that if she is my friend, then she would not contact him. What do you think?

Curious

A. Yours is a common view, so over the years I've tried to see things that way, to have your perspective of feeling betrayed by friends who date your exes.

Nevertheless, I agree only in one very narrow circumstance: when the ex caused you significant and deliberate harm.

It can be awkward, even painful; I get that. I picture, say, a sibling with an ex-spouse and I wince. But even that doesn't justify throwing our hoodies over people as if they're chairs in a middle-school cafeteria.

There's also this counterargument: If you were her friend, then she'd have your blessing to seek happiness wherever she thinks she'll find it.

There are other men on earth, of course, but for whatever reason you and he didn't work; meanwhile, she apparently sees something in him that works for her. While men may be abundant, promising connections are not. I can't endorse denying a friend such a chance.

Q. I have a close friend of many years (we're in our early/mid-20s) who has been nothing but considerate and supportive to me. I can only hope I've been as good a friend to her.

Recently she's begun seeing someone who is in a relationship with someone else. She's over the moon with new love, but I feel deeply uncomfortable listening to her stories about this entanglement. I can't reconcile the caring, giving person I know with someone who would knowingly assist in the deception and injury of another.

I've tried couching my hesitance in terms of not wanting to see her get hurt by someone who is already invested elsewhere (and also clearly a bit of a (glass bowl)), but she's waved away the objection and I don't think trying to guilt-trip her is the right thing to do.

What exactly are my options here? Her relationship isn't my life to live, but it makes me question her deeper character.

The Other Woman's Best Friend

A. You can read character in the messes people make, yes, but you can also read it in the ways they clean them up. Plus, this could still just be a bad case of the young-and-stupids.

While both of you wait for the moral of this story to unfold, I suggest you stop couching and start telling your truth. Not to guilt or judge her again, half of this story is yet unwritten but to inform. "Talking about this makes me really uncomfortable, knowing he's still with this other girl."

You can be both blunt and loving, too: "You're too good a person to stay in denial forever, but whenever you're ready to get your head out of your (dark place), it won't be too soon." Take the long view before you take a stand.

• Email Carolyn at tellmewashpost.com, follow her on Facebook at www.facebook.com/carolyn.hax or chat with her online at noon Eastern time each Friday at www.washingtonpost.com.

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