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In my experience, it was unavoidable - a close circle of friends is going to eventually involve dating someone else's ex. I've been to weddings of quite a few ex-girlfriends, and am good friends with one of my wife's ex-boyfriends.
I mean - hey, if you want someone who "saved themselves" for you, you'd better be clear about that at the beginning of a relationship, and not be a hypocrite about it, either. Otherwise, STFU.
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If you want to avoid 95% of internet spelling errors:
"If your ridiculous pants are too loose, you're definitely going to lose them. Tell your two loser friends over there that they're going to lose theirs, too."
It won't hurt your fashion sense, either.
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