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Dear Prudence: Should she tell new man she slept with his brother?

  • Article by: Emily Yoffe
  • Slate
  • October 22, 2013 - 2:29 PM

Dear Prudence: Ten years ago I was in my early 20s, living in a large city and having fun. I went on a date with an attractive man but he told me things about himself that seemed too good to be true, so I ruled him out as a potential boyfriend. But we did go to a hotel and had a tawdry one-night stand.

Today I have an amazing career that has taken me to a rural location. A year ago a new friend invited me to supper and presto, her husband is the hookup from my past. He did not give any indication of knowing who I was. I have since determined that they didn’t know each other when he and I had our date. (And it turns out he was telling me the truth about his life.) I see my friend frequently, and see them as a couple occasionally.

Because I live in a small town, finding romance has been difficult. Until now. I recently met an attractive man and we both feel a sincere connection to each other. It turns out he is the brother of my friend’s husband. Do I have any responsibility to disclose to this new man that I had a tawdry night with his brother 10 years ago?

Prudence says: Thanks for making a liar of me. When questions of what to reveal about one’s sexual past come up, I usually counsel that one’s sexual history is private except for the need to reveal one’s STD status — and when the identity of any previous lovers would be germane to a potential partner. In fact, I often use having slept with your love interest’s brother as an example of when you’re obligated to spill.

Except in your case! From your description of your encounter a decade later with your one-night stand, I think it’s perfectly possible you’re the only one who remembers this event. You say your friend’s husband did not betray a flicker of recognition when he saw you. Either that’s because he’s a really good actor or because he simply doesn’t recall all his tawdry, perhaps alcohol-enabled, youthful adventures.

I’m betting on the latter. For you to tell the brother about a onetime event from long ago would likely end your nascent romance. If he then blabbed, it would likely end your friendship with the wife, and also create terrible tension in their marriage. I say keep this part of your past in a sealed vault. I wish, though, that you had let us know what was too good to be true about your erstwhile paramour. I hope that it’s that he and his brother once bought a Powerball ticket together and won.

Send your questions to prudence@slate.com.

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