Dear Prudence

Help! My Sister Is Dating a Sex Offender.

Read what Prudie had to say in Part 1 of this week’s live chat.

Photo collage of a couple and a woman glaring at them behind their backs.
Photo illustration by Slate. Photos by ALotOfPeople/iStock/Getty Images Plus and AntonioGuillem/iStock/Getty Images Plus.

Daniel Mallory Ortberg is online weekly to chat live with readers. Here’s an edited transcript of this week’s chat.

Daniel Mallory Ortberg: Good morning, everybody. Let’s chat!

Q. Standing firm hasn’t worked: My younger sister and I don’t have a relationship with our toxic parents. Two years ago she brought her boyfriend over to my house a couple of times. Later she admitted to me that he is a registered sex offender. She really downplayed his history, which I found out by doing a simple search. He has multiple child pornography charges and was a repeat offender and went to federal prison. I immediately brought this up, and I’m still really upset because she brought him to my house without telling me, and I have two children. She made a lot of really disgusting excuses for his behavior, and she also has a child but passes it off because his charges are against female children, and she has a son—I can’t even get into how wrong that is. She’s 30, so she’s going to make her own choices, but I refuse to act like any of this behavior is OK.

All of this has resulted in me not having a relationship with her for the past two years. She keeps reaching out but still admits she’s continuing the relationship with him, so I just keep expressing my concern. It’s not going well. Nothing has changed, and I’m not sure what to do. I’m still upset that she’d knowingly hide this information from me and bring him to my house around my children. She’s said that her son has never met this person, which I’m absolutely glad about, but that proves that she knows he’s not OK, and she’s living a lie by keeping her son and boyfriend apart—meaning she’s sort of living two separate lives. She’s amazing and deserves a partner that she doesn’t have to hide from her own child. I’ve been standing my ground, but I’m in a strange position because I sort of have to be the parent? I don’t know the best way to navigate this situation. Standing firm has done nothing. Please help. I need advice.

A: I can imagine why it feels like standing firm has done “nothing” because your sister’s still with him, but standing firm once you found out about his history has actually kept your kids away from this guy and may very well have contributed to your sister’s decision not to let him spend time with her son either. That’s a great deal more than nothing. I can only imagine how distressing this situation has been for you, especially since it’s been two years now with no end in sight, but I think you’re doing exactly the right thing. I wish that made things easier.

Does your sister have any friends? Do any of them share your concerns? It might be possible for you to reach out to some of them and coordinate a conversation with her; it’s obvious that she feels very defensive of this man, but on some level she’s clearly aware that he’s not actually seeking rehabilitation and change. If she truly believed that he were committed to a new way of living, I don’t think she’d hide his sex offender status or try to keep him away from her own child. It may not happen on the strength of a single conversation, but there may be reason to hope that in time she can let go. But if she’s not showing any signs of listening and you need permission to stop having the same conversation with her over and over, you have it.

Q. I want to help someone I dated pay her divorce lawyers: A couple of years ago, I was set up on a date with a friend of my friend’s wife. My friend warned me that she brought a lot of drama with her and that I should steer clear. However, I went on a date with her and found her to be an amazing person. I was quite smitten. After the date, I didn’t hear from her for several weeks, and when I did, she said she wasn’t ready to date again just yet. I respected that and went about my life, but I was quite hurt. I didn’t speak with her after that, but after spending a significant amount of time with my friend and his wife, I kept getting more of her story.

Her marriage was horribly abusive, both physically and emotionally. I don’t have all the details, but it is something I wouldn’t wish on my worst enemy. She also has a young daughter from the marriage. As of right now, she has split custody, but from the stories I hear about her daughter’s behavior from my friend’s wife, he is doing incredible long-term damage to the child as well. She is struggling financially post-divorce, has been unable to pay her lawyer, and is fighting to get her child away from this monster. Because of the current custody arrangement, she is trapped in an area with a monstrously expensive cost of living, so whatever money she has goes to putting a roof over her head and feeding and clothing her child. It also seems that her lawyers are unwilling to help significantly until she can pay what is owed.

This past weekend I was talking to my friends, and as the details kept being told to me, I began wondering if I should help her. I have money to help her (it’s a low five-figure number, so I’ll notice it’s gone, but it doesn’t have much of an effect on my living standard), and I know there is no possible way she could pay me back. I’ve been debating whether I should pay off her lawyers (anonymously through my friends—they would take the credit for this) because I hate to see someone so wonderful being put through so much pain, and it truly pains me to see a young child go through what her father has been doing to her as well. At the same time, if I do this, I question if I am doing this for the right reasons. I still like her and, if she were interested, would like to pursue a relationship with her. What is the best course of action here?

A: I think the odds that this donation would stay anonymous are pretty low, given that you still hope she’ll reconsider going out with you. I don’t mean to suggest you’d show up on her doorstep in a few weeks to announce, “Hey, I gave you a bunch of money, go out with me,” just that this is a pretty significant secret for at least three people to keep, and I imagine this woman will be fairly curious about who her mysterious benefactor is. It’s not like getting a scholarship to college. People don’t often receive anonymous bequests to pay off their divorce lawyers.

That doesn’t mean you shouldn’t do it, necessarily, but I do think it will help to be scrupulously honest with yourself first. If you give this woman the money and it doesn’t necessarily result in the outcome that you were hoping for—namely that she’ll immediately win her custody battle—will you still feel like it was money well spent? What if that’s just a drop in the bucket and she needs to keep paying her legal fees for another year, or two, or three? What if she loses anyway? What if she finds out you gave her the money and, so far from thinking of you as her deliverer, is freaked out and wants nothing to do with you? What if you later learned more of the “details” of this case you don’t know now and found out that the situation wasn’t quite what you’d thought it was? If you can answer these questions with confidence and ease no matter the outcome, then you might consider moving forward. But if you can’t, maybe you should consider making a similar donation to a legal aid fund. I think it’s usually a better idea to save your charitable impulses for people you’re not hoping to have sex with.

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Q. Whose business is it anyway? My 37-year-old son “Chad” sent a detailed, nasty (think porn) text to my daughter’s husband’s sister “Josie.” Both are single. Josie got upset about it and showed her mom, who in turn showed my daughter and her husband. My daughter then sent it to my husband because everyone is upset at the “dirty,” apparently disrespectful words he used. (She posts pictures of her body and says gross things on Facebook trying to garner attention.) Now everyone is mad at my son except for me. My position is that they are both grown adults and can do/say anything they want, even if it’s to say “I don’t appreciate being talked to like that. Don’t contact me again.” But my husband, daughter, and sister-in-law are so pissed at Chad for it. Any time it’s brought up, we all argue. My son has not spoken to us in months over this. Am I wrong to say this is none of our business? For the record, I don’t agree with what he texted, although I don’t know what all it said, just a few words. I do agree it was probably disrespectful. How can we move past this and be a family again?

A: I’m not sure I agree with your assertion that grown adults can do or say anything they want! There are a number of things that even grown adults—perhaps especially grown adults—ought not to say or do. Some of those things are illegal, others merely immoral or ill-advised. And I’m not sure you really believe that either, because you’ve gone out of your way to make sure you don’t know exactly what it is that your son said to his sister-in-law beyond “a few words.” I think you know it was more than just “probably disrespectful,” and you only feel comfortable defending him while knowing as little as possible about what he said.

Let your adult son experience the consequences of his behavior without rushing to his defense, especially when you don’t have all the facts. If other members of the family are angry with Chad for how he treated his sister-in-law, they are allowed to be angry with him. You do not have to fix that on his behalf. You all are a family right now; just because your son behaved like an ass and a few of his relatives are angry with him doesn’t make you less of a family.

You must know, I suspect, how little I think of your argument that Josie deserves to receive unspecified but disrespectful text messages from her brother-in-law just because she posts pictures of her body (quelle horreur!) and says “gross things” on Facebook (who cares!). It’s a ridiculous attempt to deflect, and you ought to knock it off. You say you don’t know what your son texted her, but you’re not angry with him about it, but you also don’t think that it’s anyone else’s business, but you do consider it your business when other people are angry with your son, but what he said was probably disrespectful, but you don’t want to know exactly what he said … you can’t make up your mind whether this is your business or not. You want it to be your business if you think you can arrange things in his favor, and you want it to be no one’s business if you think it means other people will be upset with him. Stop fighting this battle for your son and truly commit to letting it remain his business.

Q. My brother’s new girlfriend talks way too loud: My adult brother is a decent guy, and he recently finally seems to have found a woman worth his time (his ex screwed him pretty badly). I haven’t actually had a long conversation with her because they are usually together in his bedroom when she comes over (we live with my parents). The walls between our rooms are thin, and the woman is loud! She is constantly yelling, laughing loudly, banging around, and I can hear their conversations through the walls. During normal day hours, this is a fact of life. I come from a loud family, but after 10 p.m. I make a point of quieting down because I live with several other people who sleep at night. I feel like they should do the same! It’s only courteous to be quiet at 3:30 a.m. when I have to be up by 9 a.m. to make it to work on time. I’ve tried talking to him about it, and it has not resulted in her being quiet, and my sleep is being affected significantly. She has been over to the house every day for the past two weeks, and I’m starting to feel the more serious effects of sleep deprivation. I don’t think it’s fair to tell an adult that he can’t have someone over, but I’m at my wits’ end. Moving isn’t in the cards for quite some time. Please help me!

A: There’s an obvious solution you haven’t yet tried, which is to say something to your brother’s girlfriend rather than asking him to do it for you. You don’t have to have a “long conversation” with her about it; just politely ask her to keep it down. If you’re worried about coming across as frosty because the two of you don’t talk a lot, you can smile a lot and pad your request with “I’m sure you don’t realize this, but the walls here are weirdly thin.” If you have to occasionally knock on their door and say as a follow-up, “I’m sorry to trouble you, but I’m still able to hear you really loudly in my room. Could you please speak more quietly? Thanks,” do it until she gets the message. I’d also invest in some earplugs and a fan or a white noise machine, but only in combination with a formal request, not instead of it. You might also want to spend a little more time chatting with her when she comes over, just so the two of you have a slightly warmer relationship than “Hi”/“Bye”/“Can you keep it down?” But she sounds like a pretty reasonable person; my guess is that your brother just hasn’t actually passed your concern along reliably, and that she’s likely to comply if you just come out and ask her.

Q. I want to look out for my new boyfriend’s health: I’m having a fabulous time dating a guy I chose with the help of a great therapist. We’ve been together for a year and have the most loving, peaceful, respectful relationship I can imagine. When I met him, he was carrying somewhere around 25 extra pounds. Since then I think he’s gained a few more. I cook healthy meals for us at home but have never tried to monitor or control his portions, and I know he snacks at work.

As far as appearances go, I applaud him for rocking his dad bod with apparent confidence. What I don’t applaud is him being in his mid-30s and on both blood pressure and cholesterol medication. I’ve mentioned before that I’d love to see him off of these meds, but I don’t know if it would be inappropriate to be a little more forceful about working toward that goal.

He’s very attractive to me, and I’d hate for him to think otherwise (note: I’m no supermodel, but I keep in shape reasonably well). But I also want him to be around for a long time! What would you do?

A: I suppose the most salient question is whether the blood pressure and cholesterol medications he’s on are working for him. If his numbers are good on the meds and he’s seeing a doctor regularly, I don’t think I’d advise you to be especially forceful about anything. (Unrelatedly, I’m deeply curious to know more about how your therapist helped you choose your boyfriend. Was there an audition?) You can ask him how he feels about the meds, I suppose, and if he’s ever considered taking longer walks/eating more vegetables/changing his diet to supplement them, but I think if you start assigning yourself the job of monitoring or controlling anything about your boyfriend’s diet and exercise habits, you’re going to find yourself frustrated and alienated from him.

If you talk to him and he says, “You know, I’ve been thinking about this for a while, but I’m not sure where to start,” you might start talking about taking more walks together or some other modest, achievable new habit. But if he’s not concerned (and his doctor isn’t either), and the medication is working as it’s supposed to, I don’t think you should try to convince him to stop taking it. And without trying to minimize any of your concerns about your partner’s health and long life, I think it will also be important for you to find a balance between doing one’s reasonable best to prioritize physical health and acknowledging the reality and unpredictability of death. Which is not always an easy or pleasant task, and I’m certainly not advocating passivity or pessimism in the face of mortality. But it’s important to try to strike that balance or, at the very least, to acknowledge that our fear of death (especially what we might call premature) cannot always be reasoned away.

Q. Let down after being felt up: I got hired in as my predecessor got promoted out. She used this position as a steppingstone, and it was my dream job. We hit it off, and we have become “real” friends in the years since my hire. I reported my boss—who was her boss too—for sexual harassment and sexual assault. She told me she had experienced sexual harassment from him, not in day-to-day operations like I had, but rather when she had approached him since, regarding promotions, letters of recommendation, etc. So when the lawyer my company hired to investigate asked if they should speak to anyone else, I referred them to her, since she had promised me she would share her experiences as part of the investigation. However, she withheld everything from the lawyer. My so-called friend told me that since our boss got promoted after the launch of this investigation, she didn’t think it was worth much. I said it was worth a lot because it showed it was a pattern of behavior and I wasn’t making it up. Now I feel so hurt and betrayed I don’t know what to do. She became one of my closest friends in this city, but is she, really?

A: I’m so sorry that your boss was promoted even after you went public and hired a lawyer after your assault. I want to try to read your friend’s behavior in good faith, if that’s possible, and I wonder if there’s a chance she was afraid of aiding your lawsuit because she feared retaliation, since she’s still at least somewhat reliant on your former boss for letters of recommendation and sees him as someone who could potentially tank her professional reputation. You don’t say whether you asked her in advance whether you had her permission to mention what she told you in confidence (that he’d sexually harassed her when she approached him for professional help), so it may be that she felt frightened or even betrayed when she got the call saying, “Hey, we’ve heard So-and-so sexually harassed you. Do you feel like going on the record about it?” Just because she felt safe telling a colleague at a similar or slightly lower rank about sexual harassment you’ve both experienced from the same guy doesn’t necessarily mean she felt safe going public and participating in the investigation. If you didn’t ask her in advance before giving her information and her story to your lawyer, I think you should have.

That said, I understand why you feel isolated and left out to dry—you were sexually harassed and assaulted by your boss, who’s since been promoted even after you launched an investigation. And while I think you should have checked with her first, you were placed in a terrible situation by a lecherous, dangerous boss and were doing your best to protect yourself both personally and professionally. I wish other people had backed you up, that the investigation had resulted in actual consequences, and that your boss hadn’t been promoted after assaulting you. And even if you extend as much generosity as possible to your former friend, you don’t have to resume your former closeness or trust her with any more details about your life ever again. You can wish her well from afar and prioritize your own safety and healing.

Q. P.C. pronouns: I am a registered nurse and a cis woman, and I’m currently working in a military environment where it’s customary to refer to everyone as either “ma’am” or “sir.” As I switch to a civilian hospital, I would like my language to reflect the respect I feel for all my patients. Is there a best-practice method for asking pronouns of my patients so I can refer to them appropriately and avoid putting them in an uncomfortable situation?

A: The Annals of Family Medicine published an article about communicating with trans and nonbinary patients last year that you may find helpful, although I can’t guarantee that everyone you treat will feel perfectly served if you follow this guide to the letter. My inclination, in your position, would be to use gender-neutral language by default rather than asking everyone you encounter on a daily basis for their pronouns. Not everyone wants to get into a conversation about their pronouns/transition/identity when they’re dealing with a broken foot or pneumonia, and I think the politest strategy is to replace “Good morning, sir/ma’am” with “Good morning” rather than “Good morning, what are your pronouns and how is your foot doing?”

Q. Re: Let down after being felt up: Prudie, the letter writer said: “So when the lawyer my company hired to investigate asked if they should speak to anyone else, I referred them to her, since she had promised me she would share her experiences as part of the investigation.” So the friend gave her permission and then reneged. Worse, now she has created an inconsistent witness statement that, even if she changes her mind down the road, the investigators are obliged to share with the other side. She has done irreparable harm to the letter writer’s case. If she changed her mind, she should have refused to provide a statement rather than a statement where she plays dumb and fails to mention her own harassment.

A: Oh, I’m so sorry that I missed that detail—that’s such a key point of this problem and really changes my answer. I should have caught that. Yes, if she promised to help you and then changed her story, of course it makes sense to feel betrayed and like you can’t trust her. That’s absolutely horrible. I’m so sorry to have missed that—thanks for pointing it out.

Q. Re: I want to help someone I dated pay her divorce lawyers: How does one date translate into “dated” this woman? He sounds like he has romanticized the whole situation and wants to be her knight in shining armor. I personally would be freaked out at someone I hardly know spending that much money.

A: Yeah, there’s a lot of wishful thinking going on here, and I think it’s really naive to think she’ll never find out or that this isn’t motivated by a desire to make sure she “accidentally” finds out the donor was really you someday—and subsequently feels so grateful that you saved her that she wants to go out with you again. Find an organization whose cause you support and make a nice donation to them, but let this woman handle her own problems.

Discuss this column with Dear Prudence on his Facebook page!

Classic Prudie

Q. I’m halting treatment for my cancer, but my family thinks I’m giving up too soon: After a pretty brutal year with more than 120 days in the hospital fighting a bone cancer (among other things), my condition has gotten worse. My doctor agrees with letting me stop all treatments, except things to help with pain and discomfort. I’m left with a few weeks to perhaps two years to live. I’m in my 40s, and my child is grown and doing well. While I’d like to see future grandchildren and do much more, I’m at peace. I am making the most of my time, and sharing the joy I have each day. Without the medical treatments, I experience much less nausea and pain, and I have a good quality of life for at least a short time. My family and friends, however, are not taking it so well. I hear general admonishments that I shouldn’t give up, to suggestions I seek a third and fourth opinion, to assertions I should have a bone marrow transplant (a rough procedure I would only have a 20 percent chance of surviving). What can I say to people who love me, to reassure them that it really is OK? I don’t want to spend the time I have left defending my choice to not be a hospitalized human pin cushion. Read what Prudie had to say.