Dear Prudence

I Accidentally Set My Friend Up With a Sex Offender

Do I need to tell her?

Handcuffed man walking into prison cell
Photo illustration by Slate. Photo by Getty Images Plus.

Dear Prudence,

A few years ago in college, I set my friend “James” up on a date with my friend “Erica.” They dated casually for a few months, then broke up. I fell out of touch with James after graduation and chat once or twice a year with Erica. Recently, I heard from someone else that James was in prison and confirmed it with a quick Google search. He’s serving a significant sentence and will be on the sex-offender registry for life. Not saying something to Erica about this feels like a lie of omission. On the other hand, she’s very sensitive and tender-hearted, and I’m worried she’ll be disturbed or even blame herself for not seeing signs that James could be dangerous. I also feel guilty for setting them up in the first place, even though I thought James was sweet when I knew him. Erica lives in another state and isn’t likely to hear this from anyone else. Should I tell her? If so, how? Wait until we see each other again, or send her an email? How culpable am I for trusting my friend’s safety to a person who turned out to be capable of monstrous things? Do I owe Erica an apology?

—Sex-Offender Ex

You are in no way culpable for James’ crimes. You trusted that your friend was the man he presented himself as. You didn’t have a bad instinct about him that you ignored, and you didn’t brush aside information about his character. I understand that you feel shaken, but you had no way of knowing that he would turn out to be dangerous. It would not be reasonable to treat every acquaintance like a possible sex offender, so don’t hold yourself to such a standard.

I can understand why you want to mention this to Erica on the off-chance she might find out from a more jarring or indifferent source and to put her on her guard just in case he ever tries to contact her again (unlikely but not impossible). It’s a conversation better had in person or over the phone than over email, because you’ll be better able to answer questions or provide emotional support if you can see or hear her reactions. If you feel the overwhelming need to apologize, you can tell her that you’re sorry to have to be the one to tell her. But you had no idea he was capable of criminal sexual acts, and you don’t need to blame yourself for his actions.

Dear Prudence,

My boyfriend and I are in our late 20s and have been together for over five years. We really want to move in together, but I have some hesitation about my parents. I’m not sure how to break the news to them. They’re very religious and absolutely don’t believe in living together before marriage. My boyfriend and I aren’t religious or interested in marriage. I always knew I’d have to tell my parents about this eventually, but no relationship has ever gotten serious enough until now.

They also use money to try to keep me in line. I can’t use the argument that it will be cheaper for us to rent together because they could buy me a house of my own without breaking a sweat. I have to tell them that this is an ideological difference and one I will proceed in with or without their support. But other than religious differences (which they’re unaware of) we have a really good, close relationship. I enjoy talking to them on the phone and visiting them. However, they have always made it clear that living together before marriage is the most abhorrent thing someone could do and regularly mock and ostracize anyone in their community who does it, and I am very afraid that they’ll stop speaking to me when I do it. With good reason, they’ve said as much every couple of weeks for the last 10 years. I’m not sure how to proceed.

—I Don’t Want to Be Estranged!

The “good, close” relationship you believe you have with your parents is totally dependent on your continued compliance and forced infantilization. I don’t say that to be cruel or to suggest that every fun, loving moment you’ve ever shared with your parents is totally fraudulent, but if you had a truly good, truly close relationship with them, you wouldn’t be terrified that they’d cut you out of their lives forever for moving in with your boyfriend or developing a sexual-ethical framework that’s independent of theirs. I’m sure you do enjoy visiting them, but as long as you know those pleasant visits and fun phone calls would change in a twinkling to mockery and ostracization if you told them you didn’t share their religious beliefs or that you were living with the man you love, that pleasantness rests not on a rock but on sand.

The good news is that you don’t have to allow your parents to wield money like a weapon against you—as long as you’re prepared to stop accepting money or the promise of money and property from them. As painful as it may be to watch them drop their friendly masks and turn the cruelty you know they’re capable of onto you, I think it will also come as a relief to find that sword is no longer hanging over your head, that you no longer have to pretend to be a deeply religious person with profound objections to the idea of sharing a roof with your partner. I think you know exactly how to proceed: You’re ready to tell your parents that you’re not religious, that you’re planning on moving in with your boyfriend, and that you have romantic and sexual ideals all your own. The reason you feel unsure isn’t because that’s a complicated idea to pass on, but because they’ve reminded you on a nearly weekly basis for over a decade that this is the one thing they will never allow you to do. You can survive and even thrive without their money and their conditional approval. You’ve got this.

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Dear Prudence,

My marriage ended because my wife had a late-in-life epiphany that she was gay. After we separated, she and her friend “Carole” began dating. It’s probably pointless to speculate about when they actually got together, although I can’t help but wonder sometimes. I try to concentrate on our 9-year-old daughter (we split custody fifty-fifty), but Carole keeps sticking her oar in. She calls me directly and tries to tell me how to raise my own child. They’re vegan, so I can’t take her out for pizza; I can’t take her to the fair because they’ve grounded her; etc.

I’ve told my ex I only want to speak to her about our kid, barring emergencies, and have reminded them both of our custody agreement. It works for a little while, then Carole starts up again. I recently bought a two-seater sports car and went to pick up my daughter from school, only to find out Carole had told another parent that I would be picking up her daughter as well as my own. This was news to me, I couldn’t fit both girls in the car, and Carole ended up having to leave work early to take the girl home. Everyone was irritated. Carole told me I needed to grow up and that my car was “ridiculous.” If the girls weren’t there, I would have lost my temper. I told Carole she needed to learn to stay in her lane, as she wasn’t the parent here. I ended up fighting with my ex over the phone later. I ended the conversation by saying I was done dealing with this, and next time I would be getting in contact with a lawyer. We have not been to court because I didn’t want to make my daughter’s life more difficult. My ex doesn’t make much money. I want at least to be a civil co-parent with my former wife, but Carole is making that impossible.

—Failing Civility

I don’t think it’s just Carole who’s making a civil co-parenting relationship difficulty. Your ex-wife seems perfectly happy to let her girlfriend interfere with your custody agreement and you deal with the fallout. It may seem less obvious because her passivity is less visible, but your ex is at the very least choosing to overlook Carole’s involvement. And without demonizing Carole, it’s fair for you to object when you receive after-the-fact, contradictory information about your daughter’s needs, limits, or punishments from your ex’s girlfriend. As long as your ex and Carole are together, it’s probably unrealistic to think you’ll be able to avoid Carole completely. But I don’t think your idea of getting in touch with a lawyer is necessarily a bad one. Your previous informal custody agreement is no longer serving any of you well, and it might help to get everyone on the same page and make sure that all of your obligations are laid out clearly.

That doesn’t mean you have to be maximally combative. You can reach out to your ex, see if she’s willing to meet with you and a lawyer or mediator, and ask for her cooperation, rather than saying, “I’ll see you in court and Carole in hell.” For the present, whenever possible, politely disengage whenever Carole tries to get in touch with you. You can at least decide to be calm no matter how much she frustrates you. She can’t keep you from being a civil co-parent—that will always remain within your power.

Dear Prudence,

I have known my brother-in-law for 15-plus years. My sister and he have two small children. I help them out with child care for date nights and trips. There is a conflict between him and me that has dredged up old issues. He would get upset by my washing dishes at their house.
I tried to ask why (it felt petty) and explained that I wanted my sister to come home to a clean house. She works really hard and is the primary caregiver in the household. I recently asked my husband to mediate a discussion so we can clear this up. My BIL says we are too different to get along: He is an introvert and I’m extroverted, we have no common ground, and I am impossible to have a conversation with. My sister just wants this to end and says she must support her husband in this matter.

The mediation felt productive, but my sister told me later that her husband was very upset with the situation. He felt attacked and like he could not express his feelings (he was given ample time and spent it bringing up grievances, like that I talked over him in a discussion about our shared political views). I have offered to stop washing dishes and try to be a more active listener. I can accept all of this crap. But he appears to make no effort to be respectful of me or change how he speaks or acts around me. I am resentful of the fact that he doesn’t see what he is doing is damaging. I do not want to go over there anymore. I find it triggering my anxiety disorder. I value my relationship with my sister and their children. I have been leaving before he arrives home. But it is getting to be unbearable to attend family get-togethers. Should I just let this go and continue to avoid him? Should I push back a bit with my sister, since it seems he is being manipulative? It is all very exhausting and feels detrimental to my mental health.

—Bad Brother-in-Law

I’m genuinely unclear why your husband was required to mediate a conversation between you and your brother-in-law about how often you were washing his dishes. I feel like I’m missing at least two or three crucial details as to how this escalated, so I’ll try to keep my answer simple rather than attempt to speculate: If your sister’s husband has asked you to stop doing the dishes when you babysit, and your sister says she supports him, then stop doing the dishes when you babysit. Let the two of them figure out what division of labor works for them, even if it’s not a division that would work for you. If you decide you don’t want to babysit for them at all anymore—which you’re perfectly entitled to do—then stay at home and do something you enjoy.

Part of what’s confusing and a little concerning is that I have a pretty clear picture of what your brother-in-law’s objections are, but you’re curiously (perhaps purposely) vague about what he’s doing that bothers you now. How does he speak and act around you. Is he ignoring you? Calling you names? Speaking snidely or rudely? Without knowing more about what it is that he’s doing to upset you, I’m forced to conclude that although he may be responsible for his fair share of this quarrel, you go out of your way, at least some of the time, to make things difficult. Please do not “push back” with your sister over an argument about the dishes that should have ended long ago. If the best you can do is avoid your brother-in-law whenever you can, stay polite but distant when you can’t, and focus on the kids, that seems like a reasonable and achievable goal.

Dear Prudence Uncensored

“This could have been the easiest conversation in the world.”
Danny Lavery and Nicole Cliffe discuss this letter in this week’s Dear Prudence Uncensored—only for Slate Plus members.

Dear Prudence,

During a recent visit, I noticed that my father was growing increasingly impatient with my 3-year-old. At one point, my son dumped some crumbs from his stroller tray onto the floor at the supermarket. My father grabbed the tray from him and pushed him hard against the side of the head. I immediately intervened and told my parents that “we do not hit in this family.” Growing up, my mother had been strict, but my father was controlling. He hit me until I went to college out of state. He used cruel and demeaning language. He often hit me in the head, sometimes knocking me into walls. I had compartmentalized different aspects of my parents in my mind in order to try and build a healthier relationship with them as adults.

Later that evening, they dismissed my concerns, minimized what my father did, talked over me, tried changing the subject, and then threatened to leave right then and cut ties. I told them to stay in hope that we could make some progress. But they just pretended like nothing had happened. I am reeling. I am prepared to cut them out of my life unless they can assure me that they will not physically harm my children. I am looking into therapy to work through this. But in the short term, I am not sure how to respond to people who ask about my parents. I don’t mind being purposefully vague with acquaintances or strangers. But I am unsure what to tell people to whom we are not close but we see on a regular basis—for instance, day care teachers and neighbors. What would be enough information to tell people so that they know not to talk to my children too much about my parents but also not to ask me too many follow-up questions? I feel the need to protect my children and to protect myself, but I also feel like I’m drowning.

—Stopping My Father

I’m so sorry. You’re doing the right thing, which may not make this feel any easier, especially as long as your parents continue to pretend that they don’t know what you’re talking about, that you’re making things up, that it was just a little shove—he barely touched the kid, that you were always too sensitive and prone to exaggeration, and so on. I hope that you’re not being asked, “Hey, where are your kids’ grandparents?” regularly by your neighbors and day care providers. But if you need a brief script to signal that you’re not looking to go into detail, this should fit the bill: “We’re not sure when we’ll see them next, but we’ll let you know if anything changes on that front. Thanks for understanding.”

Dear Prudence,

I am a bisexual widower in my mid-50s. My wife was a remarkable woman and the love of my life. She died two years ago after a wonderful 30-year marriage. I decided if I was ever ready to date again, I’d be interested in both men and women. Last year I met “Eric,” and we hit it off immediately. We spend a lot of time together; he’s very smart, talented, successful, and a lot of fun (plus he’s good-looking). Normally I have a fairly good intuitive read on other people’s orientations once I’ve gotten to know them, but I’m drawing a blank with him. Other friends who know Eric well have commented on our surprising closeness, saying that he usually prefers to do things by himself. He hasn’t dated in over 20 years and has apparently never had a serious relationship. We live in a fairly conservative community, which may have an impact on this.

Recently we were having dinner at my place and put the news on in the background. A male celebrity had recently come out as bisexual, so I decided to mention that I was too. Eric replied, “Interesting,” as if I had said “My favorite color is blue.” Then he moved on to another topic. I figured that may have turned him off. But he called the very next day, and it has made no difference in our friendship. He never comments on the attractiveness of either women or men. Maybe he doesn’t notice. Is it ever OK to straight-out ask someone about their sexuality? I want more of a relationship with him, but I don’t want to insult or upset him by being intrusive. If he’s not interested in romance, I’d happily keep him as my best friend and pursue romance elsewhere.


You don’t have to resort to something as bald as “Enough is enough, Eric—what’s your sexual orientation?” in order to ask if he’s interested in going out. But there’s nothing rude or intrusive in asking someone if they’d like to date you, even if the answer is no. You can tell him: “I don’t know if you’ve ever considered dating men, but I love spending time together, and I’d have a lot of fun taking you out on an official date. But I’m happy to stay just friends if that’s not what you want.” Good luck!

Classic Prudie

My just turned 18-year-old son, who is a senior in high school and lives at home, recently came home and told me he has his first girlfriend and that he is in love. He said she is older than he is. He looks a bit older than 18. Turns out his new love is 48 years old. That is a year older than me. I met her, and she is actually very nice and in love with my son. If I had grown up in this town, we would have been in school together and likely best friends. She is not his teacher or in any position that would be suspect. They simply met in a cafe and fell in Love. Is this OK?