Dear Prudence

I Found My Stepsister on a Sugar Daddy Website

She blew up at me when I asked her to hook me up with her “friends.”

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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.”

Dear Prudence,

My husband and I have an open adoption with our 3-year-old son, “Josiah.” “Melody” was 18 when he was born, and we all committed to ensuring her presence in his life. We’ve had video chats twice a week, and physical visits once a month. But Melody’s life has become increasingly chaotic, and it’s spilling over into our lives, too. She dropped out, can’t seem to hold down a job, and keeps bringing new boyfriends on her visits, even though we asked her not to. She said it was just because she needed a ride from them, but my husband has offered to drive her. Melody’s also asked us for money—first $20 here or there, but then she called us one night crying because she was about to be evicted and her ex stole her money. We gave it to her but wanted her to file a police report. She didn’t and refused to talk about it again. She also refuses to explain why she moved out of her mother’s house or why she will not seek help from her relatives.

We want the best for Melody, but this is too much for our family. Coronavirus has stopped the physical visits and we have been whittling down the video chats. We don’t know what to do. Back when our son was an infant and Melody seemed to have her life on track, we imagined her being a part of our lives forever. Now we just don’t like this chaos affecting our son. We don’t know if it is drugs or mental illness or what. Melody never seems high when we speak to her, but she keeps making bad choices. What do we do?


In a word: less. You have every right and reason to set limits with Melody, like if she wants to bring a man you’ve never met to spend time with Josiah or if she asks you for money. It can be hard to say “no” when someone’s crying on the other end of the phone, but it sounds like giving her money has only ever complicated your relationship with her and done little to help. If she brings a stranger with her to your next in-person visit, you can either say, “It’s nice to meet you. This is a family visit, so you can’t come in, but Melody can give you a call when she’s ready to leave” or invite him in for a cup of coffee and a chat, while Melody and Josiah spend some supervised time together. I also think it’s fine to shift from twice-weekly video chats to weekly ones, as long as you’re clear with Melody first, so she’s not surprised or left wondering why you’re not taking her calls.

But if she doesn’t want to tell you about her problems with her own relatives, don’t pry. Focus on the time she’s able to spend with your son, and exercise your rights and responsibilities as parents judiciously, but don’t try to get her “back on track” or steer her away from chaos. She’ll resent you for your interference, and it won’t do you or your son any good to try. She’s not raising him, and it doesn’t sound like she spends time with him without you there, so while you may personally dislike the fact that she dates a lot or doesn’t have a full-time job (that you know of), you don’t need to do anything about it. It’s likely that Josiah will grow up with some understanding of his birth mother as a chaotic, if affectionate, person, and you don’t need to shield him from that. If they enjoy their weekly calls, and he’s safe and well-looked-after by his parents, there’s a real limit to how much Melody’s chaos can affect him. Don’t sever her connection to Josiah just because she’s unemployed, or fights with her mother, or doesn’t conduct her personal life the same way you would.

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Dear Prudence,

I have a teenage stepdaughter who has officially “blossomed” into womanhood. Always a small child, she’s still on the shorter side, but definitely not petite. Neither is she overweight, but I feel she should dress more appropriately. I don’t necessarily mean “conservatively,” but rather her clothes are too small—everything is too tight and too short, and it looks like she should wear things one if not two sizes larger. My husband still sees her as tiny, and her mother is not a parental figure at all, but telling her to wear a larger size puts me into evil stepmother territory. Is there a way to discreetly tell her that her clothes don’t fit?

—Not Evil, I Promise

If your stepdaughter’s clothes don’t fit because neither of her parents have bought her any new clothes since her last growth spurt, then by all means set up a shopping trip. You don’t have to be “discreet” or whisper in shocked tones that your teenager is growing. That’s pretty common for teenagers! That doesn’t mean you should announce “I’m taking you shopping because it’s obvious none of your clothes fit you anymore” over the breakfast table, either, but if your kid’s getting too big for her clothes, you buy her new clothes. If some of the new clothes she wants to buy are skimpier or more form-fitting than you’d like, then you can debate norms among kids her age, find a satisfactory compromise, and engage in classic (step)parent/child dressing-room warfare. This probably won’t be the last time she wears something you don’t love, but it’s important to keep things in perspective. Go get her some bigger shirts, but don’t try to micromanage her appearance or stress out about an inch one way or the other on a hemline.

My last point is comparatively minor, but a teenager having a growth spurt is not the same thing as “blossoming into womanhood.” She’s going through puberty and she’s growing up, yes, but she’s still a girl, not an adult woman. Too many adults still treat girls who develop bigger hips or busts as if they’re older than they actually are. That’s not to say you’ve been robbing your stepdaughter of her childhood by using a relatively common phrase—it’s clear that you’re trying to look out for her, not run her down—but I think it’s a phrase best left in the past.

Help! How Do I Stop Being So Mean?

Danny M. Lavery is joined by Michelle Dean on this week’s episode of the Dear Prudence podcast.

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Dear Prudence,

My husband’s dog is very old and has many health problems. I often have to separate him from our small children for their safety and comfort (both the kids’ and the dog’s). There might be some life-extending procedures available to him, but they’ll be very expensive and won’t do much to improve his quality of life. My husband and I have been together for 10 years, but the dog predates me. I love this dog too, but I’d rather leave the decision-making up to my husband. But I’m the one taking him to his next vet appointment later this week, and I have a feeling I already know the prognosis. I’m worried that if I even bring up euthanasia my husband will freak out or that he’ll agree to it but secretly resent me for saying it first. The last time I had to decide to put a dog down, he was mine, 14 years old, and was days away from dying of pancreatitis, so there was no question about what to do.

I’ve always believed and taught the kids that pets are forever. I feel terrible. I’ve known this dog for over a decade, I care about him, and I hate that he’s in pain. Am I selfish? The dog is miserable, but my husband says the idea of putting him down makes him physically ill. I don’t know what to do. I feel as though my husband is leaving this on me on purpose and I can’t win no matter what I do.

—Cruel to Be Kind

I think you’re right. Your husband is letting this fall to you, not out of malice or indifference, but because he’s so afraid of having to make this decision himself, and experiencing the pain he’s been dreading, that he wants to avoid it at all costs. That’s understandable, but it also needs to stop. His dog is suffering, and you’re anxious about your ill-defined role. You don’t have to take a tough-love approach when you talk to your husband about this, but I think you should stress the need to prioritize the dog’s suffering over human angst. Do this before the vet visit, even if you still end up going alone. Tell your husband that you’re not looking to make this decision for him, but you need to know what questions to ask the vet and which treatments to consider once you’ve received a specific prognosis. He should consider the dog’s day-to-day experience, not just his own sadness, as he contemplates options like pain management, euthanasia, or further treatment: Does the dog still enjoy going on walks? Can he move without pain? Does he still have an appetite? Is he still able to do his favorite things with some regularity? What are some specific indicators that your husband thinks would signal the time to schedule a euthanasia appointment? I’d encourage you both to write all of this down so you can refer to it without having to rely on subjective impressions while you’re both sad.

Now’s probably also the right time to add a layer of nuance to the “pets are forever” line you’ve been using with your kids. I imagine what you’ve previously stressed to them was more along the lines of “A pet is a serious commitment and a part of the family, not something to be acquired on a whim or abandon if you get bored” than “This dog will never die,” but once you and your husband have discussed it, you can talk to the kids about death, the difference between quality and quantity of life as it applies to animals, and about sadness and grief. Death is forever, too, and it’s OK to be honest with your children about that.

Dear Prudence Uncensored

“In general parents die a lot less from surprising news than people claim they will.”

Danny Lavery and Christina Grace Tucker discuss a letter in this week’s Dear Prudence Uncensored—only for Slate Plus members.

Dear Prudence,

My boyfriend of seven years and I have finally decided to get married, which is very exciting! Our wedding is going to be small but most of the guests will be my fiancé’s family from out of state, whom I have never met. I am a trans woman, and I’m certain most of his family (excluding his parents and brothers) already know that. While his immediate family are kind and supportive (more so than my own), he has occasionally confided in me about his relatives’ racism and homophobia, which he sees on Facebook. I’m worried about the possibility that one of them will make a scene when they meet me. How can I best avoid this? I don’t want to bar his family from coming (especially since we’ve already sent out save-the-dates), but I don’t want to be the focus of cruelty or bigotry, either. My fiancé has assured me he’s going to do everything he can to make me comfortable and happy, but I don’t want him to have to make sacrifices for what should be our special day.

—Terrified Bride

It will help not to think of it as a “sacrifice” for your fiancé to make sure no one harasses either of you on your wedding day. That is not a sacrifice in any meaningful sense of the word! It is part of what will make your wedding day special—a celebration of your relationship, rather than a test of endurance with a bunch of hostile, bigoted strangers. I don’t know if you want your fiancé to share the fact that you’re trans with his relatives in order to preemptively screen out the anti-LGBT contingent. If you do, he can let them know that anyone who has a problem with trans people isn’t welcome at your wedding. (Normally I don’t advise couples to uninvite people who have already received save-the-date cards, but homophobia and transphobia, or any objection to the nuptial couple’s relationship, is a big exception.)

If you don’t want him to share this information with relatives you’re not sure about—which would be perfectly understandable—he still has grounds to speak to the ones who regularly post homophobic and/or racist updates on social media and let them know he objects. This isn’t just a question of your comfort and safety (although that’s certainly critical), but of his values and the kind of life you plan to build together. Not inviting openly bigoted, anti-queer people to your wedding is a no-brainer. Err on the side of caution: If your fiancé isn’t completely certain that a given relative won’t cause a transphobic scene at your wedding, they don’t get an invitation, full stop.

Dear Prudence,

Four years ago, I applied to several great out-of-state colleges and was accepted at all of them. I was offered scholarships but would have had to take out loans to cover the rest, and my parents weren’t willing to cosign with me (I graduated high school at 16). So I went to the local state school for free. I understand my parents had the right to decide not to take out loans, and I don’t have hard feelings about it. But I had a lousy time at college. It wasn’t a good fit, and I felt like a total outcast. I’d hoped to be around creative, curious people, but most of my fellow students were stoners and/or jocks. I know that sounds judgmental and is probably an oversimplification, but I just didn’t have much in common with the rest of the student body. I tried to make the best of it but was always just the weird girl on campus. I didn’t get close to anyone and spent most of my time working while my actual friends went to big-name colleges and seemingly had the time of their lives. I didn’t even get a solid education out of it. Most of my professors were overworked adjuncts who never had time to give feedback beyond “Good job.”

I’m graduating in December and my parents and grandparents all want college “merch” to celebrate. I hated my college experience and feel embarrassed I even went there. I just want to move on, but it’s going to be hard if they have alumni stickers and T-shirts. Is there a way to tell them I don’t want to celebrate the worst four years of my life? Or do I just wait until grad school and buy them sweatshirts then?

—Unhappy Alumna

For whatever it’s worth, I had a lousy college experience myself and wish I’d done anything else with those four years besides spend it at a homophobic evangelical Christian outpost in suburban Los Angeles. That’s not to say “but my life turned out fine, so it was all worth it in the end,” or to reassure you that someday you’ll feel happy or even neutral about your school. It’s fine to just hate it! It’s fine to not want to associate with it, either. Eventually, those four years will take up a much smaller proportion of your life, and it won’t feel anywhere near as important as it may now. I don’t think you’ll have much luck trying to persuade others never to speak the name of your alma mater in order to help you forget, but you can certainly tell them you’d rather they found other ways to express their pride over your graduation. But let it go after that and focus on what you want to do next.

Let me also put in a plug for skipping your graduation, if you feel so inclined. Even without taking the pandemic into account (which is a pretty big “without”), there are plenty of good reasons to do something else with that time. It’s a long ceremony, with a lot of sitting around, and if you don’t find the idea meaningful or compelling, I don’t think you’re going to suddenly bolt up in the middle of the night at 70 and think, “My God, I never went to my college graduation—how bitterly I regret that now.” Get out of there, and good luck with the next four years. I hope they’re a lot better.

Classic Prudie

My parents went on vacation and my father asked me to answer email from a client on his behalf, because he was cut off from the Internet. While searching for the relevant emails, I came across a couple of messages that had subject lines such as, “Hi Dad, I love you.” These were not from my siblings. I dug through his inbox and found several messages from what sounded like a teenage girl calling my father “Dad.” I also found a few angry emails from the same address that I’m assuming were from the girl’s mother. My parents have been married for almost 40 years, and I had always assumed they were happy. I don’t know whether to tell my siblings—we’re all adults—about this, confront my father, or reveal this to my mom. My mother is completely dependent on my father financially and emotionally. I am going to be married soon and this makes me lose all faith in marriage and relationships. My father was my hero both as a husband and father, and if he is this sleazy I am not sure how my fiance and I stand a chance. Do my siblings have a right to know what going on? What is the path of least harm?