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Dear Mahvelous,
A friend of mine, Sara, is dating a guy I dated a few years ago. She’s all starry-eyed about him, but he has always been a player. We have a get-together with friends coming up and I know she is bringing him as her “plus-one.” I haven’t told her that I once dated him or all the things I know about him. How should I handle this? — Erika
Dear Erika,
Some things are witnessed best au natural, meaning wait and see what happens naturally. Don’t let the impulse to fess up take over your common sense — wait and see how he handles it when you meet and then take it from there. Although my own friends call me the eternal optimist, I would say I’m more the eternal pragmatist. So maybe the guy has done a 180, really likes your friend, and there is something of value between them. If he is friendly, self-deprecating and brings up your previous “friendship, “ then take it at face value that he’s not trying to do the cover-up with Sara (that is, if you are still remotely recognizable as the Erika you were then). If, on the other hand, he won’t look you in the eye and pretends like he’s meeting you for the first time, that’s your clue to give Sara the heads up.
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