Dear Prudence: I once had a one-night stand with my new crush’s brother.

Help! I Once Had a One-Night Stand With My New Crush’s Brother.

Help! I Once Had a One-Night Stand With My New Crush’s Brother.

Advice on manners and morals.
Oct. 17 2013 6:00 AM

Once Upon a One-Night Stand

I slept with my new crush's brother long ago. Should I come clean?

Emily Yoffe.
Emily Yoffe

Photo by Teresa Castracane.

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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?



Dear Wondering,
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, you’d 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.


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Dear Prudence,
My parents divorced when I was 5 years old. I have a strong and loving relationship with both my parents and each has remarried and started new families, which means I have much younger half siblings, whom I also love dearly. My father and stepmother never helped me financially through college, though their house and lifestyle would lead me to believe they could have. I worked to pay for college, lived at home, and made excellent grades. But I am saddled with over $100,000 in school debt. Now my younger sister has started college. My father and stepmother have been paying a significant amount of her tuition, are helping with day-to-day expenses, and encouraging her to study abroad. She's stated that she’s been told "school is her job" and she doesn’t have to work. I feel like I need to distance myself and cool off, but still want to share with my father how unfair this all seems to me. How do I deal with the anger and resentment I feel toward my sister and the "second family"?

—Frustrated First Daughter

Dear Frustrated,
It’s always a good idea to cool off before you confront a difficult situation in which you are going to seek redress. Your goal should not simply be to unload to your father about the disparities in the opportunities you two sisters have had, but to open a discussion with him about the burden you carried alone for your own education. You can say that seeing how he and his wife are easing much of the financial load for your sister has made you wish you’d had the emotional wherewithal when you went off—make that stayed home—for college to talk to him about getting assistance. (You have left your mother out of the equation. I’m assuming you were living with her and that she didn’t have funds for your education.) Explain you maintained excellent grades while working your way through school. But you couldn’t earn enough to pay the tuition, and you now have a six-figure debt. Explain how this is impeding your ability to launch your adult life, and you are asking that he help pay off part of your college loans. I hope your father will consider your request and come through for you. If not, then you will have some understandable anger and resentment to work through, but keep in mind the person behaving unfairly is your father, not your siblings.