What I’m getting at is “let it go or let her know” is a superficial way of looking at this. Telling her may do a lot of permanent damage—including to your existing friendship. If you don’t tell her, yes, your friend may cheat again. Or he may not. What I really want you to do is look at your own motivation for even thinking about telling her. Sometimes people “do the right thing” out of self-righteousness, self-protection, or even revenge. (Any reason you’d want to break up this relationship?) If you’re truly concerned about this woman’s heart—and only you know if you are—go for it. Tell her. But you may end up bearing a burden that I’m not at all convinced you’re ready to handle.

She Said: If this woman was a close friend of yours, my answer might be different. But given that she is your friend’s fiancé, telling her would not only be disruptive and damaging, I actually think it might feel more disrespectful to her than the cheating you’re referring to. For all you know, they had an agreement (this is San Francisco, remember?); for all you know, she’s also cheated and admitted it and therefore he got a “pass”; for all you know, the affairs were the very experiences that gave him perspective and made him ready to commit to her.

I’ll make this simple for you. Pretend you live not in the United States, where Puritan forefathers and neo-cons have conspired to have us believe that sexual monogamy is the sole way to build a successful long-term marriage, but in, say, France or Italy. In those countries, a groom’s friend would never think of telling the bride-to-be that her fiancé had a few flings prior to the engagement.

Take it from someone who has seen families torn apart by loose lips, and who has experienced the insufferable proddings of well-meaning friends (with wholly different value systems, by the way) into her own marital troubles. Mind your own business. Capisce?

Send your questions to Twosense@7x7.com