Dear Prudence

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.


Dear Prudence,
I have curly hair. At times it can be hard to control, but when it behaves, I do get lots of compliments on it, and have grown to really love it. As a child I hated the knots and tangles, and all the barrettes needed to keep it looking tidy. My sister, who has straight hair, has a 4-year-old daughter with curly hair. My sister is now acting as though her daughter has some sort of defect that must be hidden from the world. Every morning my sister subjects her little girl to blow dryers and flat irons. She even avoids taking her outside when it’s rainy or misty out, lest her hair “frizz out.” I feel like this will only get worse as she get older, and am afraid this will hurt my niece’s self-esteem. Should I say something to my sister, or am I just being biased because I too have curly hair? 

—Mop Top

Dear Top,
How sad that your sister is maligning the natural beauty—and hampering the freedom—of her darling little girl. Soon enough, your niece will be a teenager obsessed with her looks, and she will devote way too much time to taming her locks. But the mother of a preschooler shouldn’t be spending more than a few minutes a day tending to her daughter’s hair. Putting it in a pony tale or clipping in a couple of barrettes is all it should take. Keeping her indoors so her hair doesn’t frizz is oppressive and undermining. I think you should say something. I hope you can keep it light and humorous and say as a representative of the curly-haired caucus you want to speak on behalf of your sisters (if not your biological sister) and say you would like to see her celebrating her daughter’s gift, instead of frying it into submission. Tell her you spent too many hours as a girl feeling bad about your hair, but now that you’ve learned to love it, you enjoy the freedom of letting your curls fly and the compliments they bring. If your sister won’t put down the styling equipment, then make sure you have your niece over for sleepovers. Then you two can give each other shampoos and she can learn to celebrate the corkscrews that emerge.


Dear Prudence,
I have been blessed with the fact that my 16-year-old son and my husband, his stepfather, have a wonderful relationship. This year we are having a Halloween party at our house and they have decided to dress up as Walter White and Jesse Pinkman from Breaking Bad. My husband has an orange painting suit, complete with mask, which my son would wear. I am a huge fan of the show, but the mother in me thinks this is not a good idea. They would not be going out in public, but pictures will inevitably end up on social media. My son is a good kid, into sports, and does not do drugs. I have told my husband that having my son dress up as a meth dealer would probably be considered bad parenting, but he says it is all in good fun and that people dress up as worse things for Halloween. What do you think?

—“Bad” Mother

Dear Bad,
went into mourning when Breaking Bad ended, but even though week after week Slate writers exalted the show, no one took that to mean they thought meth dealing was preferable to blogging (even if potentially more lucrative). Every Halloween I have children coming to my door dressed as Freddy Krueger, and although some readers say I have a penchant for recommending people call Child Protective Services, this costume has never made me think these little killers have criminally bad mothers. After all, Halloween is largely about inhabiting your own nightmares. During the George W. Bush years, many parents got their children W masks, and they weren’t doing it to celebrate the president, but because they thought it was the most horrible image they could imagine. The fun of Halloween is in letting loose, and it’s beautiful that your husband and your son have such great chemistry that they want to bond over their mutual love of show about a chemistry teacher.


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