Dear Prudence: I Found My Stepsister on a Sugar Daddy Website

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Dear Prudence,

I just came out of a toxic divorce. I messed around online and found out my 23-year-old stepsister has several profiles on “sugar daddy” websites. She still lives with our parents and has college loans. My mom thinks she does web design. In the most awkward email of my life, I told her she needs to clean her accounts and come up with an alias. This will haunt her later in life and ruin her reputation now, plus it will kill our parents. She never responded but her accounts vanished.

I tried to get back in the dating game but realized I have too much baggage. I want sex, but I don’t have the emotional capacity to commit to anyone. I emailed my stepsister and asked her if she had any “friends” she could recommend for a short-term sugar daddy situation. She called me a pervert and went on a ludicrous rant about my character. I told her not to be coy—she was selling sex. She doesn’t get the high moral ground here. She threatened to tell her father; I told her I would be there with popcorn. I told her that I don’t think what she was doing was “shameful” but neither was me asking about it. She cursed me out and then blocked me. Now our parents are wondering about the rift. I have told them to ask my stepsister. We didn’t grow up together, but I thought we had a fairly civil relationship. What is my next move here?

—My Sister’s Keeper

A good old-fashioned apology! Not an apology coupled with another request for a favor, and not an apology coupled with another justification of your behavior, and certainly not an apology coupled with any of your opinions on sex work—just a brief, sincere apology, followed by a respectful distance.

 

I think you know how very badly you have treated your stepsister or else you wouldn’t be working so hard to try to acquit yourself by first accusing her of being responsible for killing your parents, then by accusing her of coyness when she didn’t give you what you wanted. “If you’ve ever done sex work, you have to say yes to whatever I ask of you” is a repellant approach to a relationship. Trying to dress it up as who has the moral high ground just won’t wash.

 

If you’d like to pursue casual sex with no emotional commitments, you don’t need sugar-baby websites in order to do so. If you’d like to pursue casual sex and get paid for it, don’t seek advice from a relative you’ve recently scolded and ask them to set you up for free. If you’d like to have a peaceful relationship with your stepsister, don’t casually announce you’ve found her sugar-baby profiles and think she’s ruining her life forever via email, then call her up a few weeks later and say, “Do you think any of those people would have sex with me?” You behaved boorishly, hypocritically, condescendingly, cruelly, and with tremendous entitlement. You should apologize and then back off and give your stepsister time to decide what kind of relationship, if any, she wants to have with you. You’re both adults, and you don’t have to inform your parents every time you get into a fight. But if they ask again, and you do want to share something, you can always say, “I treated her badly, and she has good reason to be angry with me. I’m working on it.”