Help! My Brother’s Escort Habit Is Threatening to Break Up … My Engagement.

A woman and man argue face to face in front of a broken pink wedding band ring.
Photo illustration by Slate. Photo by PeopleImages/iStock/Getty Images Plus.

Dear Prudence is Slate’s advice column. Submit questions here. (It’s anonymous!)

Dear Prudence,

My older brother lost his wife suddenly when he was 28. She was literally the girl next door and they’d been together since they were 14. It was devastating and I don’t think he has ever really gotten over her loss despite grief counseling and time. He briefly tried dating about five years after she’d passed but said it felt empty and hollow and he didn’t enjoy it. Fast forward 14 years and he is a successful businessman with a lot of hobbies. His life is pretty full but he gets lonely sometimes and wants human connection, but not a commitment. With the popularity of hook up apps, he is able to have his sexual needs met and when he wants to go out to dinner or have companionship on a date, he hires an escort. He has two escorts he has been seeing for about three years. He told me he does not have sex with them, but that he likes to go on dates with them because there is none of the awkward first date conversations and getting to know you period. One is a career escort and the other is paying for law school. I have met them both and they seem like nice women and the arrangement seems to work out for everyone involved. There are only a handful of people who know they are escorts, and he doesn’t usually bring them as dates to family functions.

Recently, my fiancée and I were going out for dinner and ran into my brother and one of the escorts. We ended up joining them for dinner and the live music they were seeing after. My fiancée really hit it off with my brother’s date and talked afterwards about meeting up with her and how she was so glad to see my brother with someone. She kept pushing in the days after for us to do another double date, so I broke it to her what their arrangement was. She was not only taken aback but finds the whole thing “disgusting.” She called my brother pathetic and immoral and doesn’t want him to be the best man at our wedding. We had a big fight where I told her if my brother wasn’t invited, there wasn’t going to be a wedding. I pointed out that her sister had an affair that ended her marriage, as well as her affair partner’s marriage, and yet her sister was her maid of honor and the affair partner was a guest. I told her I thought that was more egregious than having casual sex with Tinder hookups and hiring escorts to go out to dinner.

We are now at a stalemate. We are sleeping in separate rooms and haven’t spoken for about a week except to fight about how unreasonable the other person is being. I will absolutely choose my brother in this situation and am ready to call off the wedding. She thinks that means I don’t love her. I do love her but don’t want to marry someone who calls my brother “pathetic and disgusting” and has no empathy or understanding for his situation. Should I keep trying to get her to understand? Just call off the whole thing? My brother would be devastated if he knew he was the reason our relationship ended, but I also don’t want him to know how my fiancé feels.

—Brother’s Keeper

Dear Brother’s Keeper,

If I have a general rule about this kind of situation, it’s probably something like: If you’re talking about the possibility of calling off the wedding, just go ahead and call off the wedding. I have a strong, strong feeling that you and your fiancée aren’t super compatible people who just happen to have one random difference when it comes to the ethics of using escort services. Instead, I think it’s very likely that your conflict represents a larger difference in terms of worldview, values, and tolerance for others’ choices. Not to mention major struggles with handling conflict. But I know calling off a wedding is a huge, stressful, intense thing. So let’s test out my theory about incompatibility a little. Here’s how: Have a conversation with your fiancée that starts with how much you love her and how you regret keeping her in the dark about the nature of your brother’s relationship. Explain that you won’t be okay if he’s not in the wedding, and ask if you two can agree to disagree about his love life (meaning, the “pathetic and disgusting” talk has to stop) so that you can focus on your own and move forward with the marriage. She might be disarmed by your apology and agree. And maybe you’ll be able to start a new habit of working through issues together rather than battling each other. But if she digs her heels in and continues to fight you, get out of this situation. Please. It will seem catastrophic, but there are a lot of other paths to happiness available to you. If you need inspiration for how to think creatively about that, just talk to your brother!

Sometimes even Prudence needs a little help. This week’s tricky situation is below. Submit your comments about how to approach the situation here to Jenée, and then look back for the final answer here on Friday.

Dear Prudence,


My husband is a yearner. Most of our conversations are centered around something he’s looking forward to, a piece of tech he’s coveting, a social group he wants to start, the city he wants to move to, how we should get a new pet, etc. I used to admire his passion and ambition, but now after six years of marriage I just think of him as a blowhard. He’s always talking about the next thing he wants and is rarely satisfied with the present moment. In fact, even when we’re actively doing something really fun he’ll fixate on “why we aren’t doing this more often?”! I try to humor him and genuinely hear him out without thinking to myself “ok sure, we’ll see about this one,” but it’s getting harder as time goes on and it seems like he’s almost always unwilling to take action on the stuff he’s always talking about.


For example, I’m really happy with where we live. We worked super hard for years to buy a house in a desirable town close to a bigger urban city. I’ve made a lot of friends here, and both of our careers are specific to our region. Our town is progressive, safe, beautiful, the weather is nice and there’s plenty to do. It is absolutely inconceivable that we would move from here without years and years of focused work and savings, even if we *both* wanted to—yet he talks about wanting to live in a major coastal city like New York or Seattle practically every day. And it’s not just musing, he expresses a bitter judgment of our town, the culture here, and lack of certain activities.


I am so tired of it. I don’t feel that I can trust for one second that if we actually changed our whole lives for his plan that he wouldn’t just find some new lifestyle to yearn for. I feel like even if I said “sure, let’s move to NY/get a new cat/replace our sound system,” I would be stuck with all the work while he moves on to the next dream. I’m starting to feel like I don’t know how to talk to him anymore. Our day to day interactions have become a lot of him telling me all about something he wants or thinks would be cool and all I have to say is “mmhmm.” He talks too much, is completely disconnected from our present day lives, and would spend everything we have on whims if I weren’t bearing the burden of 100 percent managing our finances. I’m so bored and feeling like my experience of having slow and steady goals, and being mostly satisfied with life, is boring to him in return. It doesn’t feel like we genuinely have misaligned deeply held goals, it feels like he habitually and pathologically craves novelty. What can I do here?


—Is This Growing Apart?

Dear Prudence,

I need advice on how to deal with a friend whose selfishness is really, really getting to me at the moment. She has always tended to be one of these people who has to “one-up” you when it comes to hardships in life—e.g. you say that you didn’t get much sleep last night, and she’ll laugh and say, “Yeah, I’ve had insomnia since I was 10, so I don’t even REMEMBER what a good night’s sleep feels like!” I once complained about ableist discrimination I faced at my work (I’m partially deaf) and instead of sympathizing or even asking me what the outcome was, she turned it into a conversation about the discrimination she faces as someone who needs a walking stick. There are many, many examples, but you get the idea.

Aside from this habit, she is a great friend in many ways—she put me up when I was homeless once, we laugh a lot together and bond over some niche shared interests. But her selfishness is becoming a real problem. I recently messaged her about a very serious crisis I’d been dealing with —I was violently sexually assaulted at work, my partner has fallen sick, and my mental health has been devastated as a result of the above. I sent her a message saying what was happening and indicating I needed someone to talk to about it. She didn’t respond for three days (unusual for her) and then replied with a lengthy message about her own current mental health crisis, which she made sure to emphasize was worse than mine (“I don’t have a partner to support me either and actually needed hospital”) and included not a single question about the things I had told her about my situation. I was too angry and upset to reply. My question is, what on earth do I say?

—She Always Has It Worse

Dear Has It Worse,

What your friend is doing here by making everything about her is extremely common. I think many people who do it actually believe it’s a normal and helpful way to normalize any difficult experiences others may be having. The most generous read of the habit is that she’s thinking “I can let my friend know she’s not alone. We’re all suffering and there’s nothing wrong with her.”

But even if that’s the case, being aware of it doesn’t help you when you are in the midst of a really difficult time and need someone to talk to. You’re struggling deeply and you deserve understanding, kindness, and helpful feedback if you want it, not “Oh yeah I have that too, or worse.” The best way to get that is to turn to someone who already understands how you’d like to be listened to and talked to, instead of trying to retrain this particular friend. Would you be open to lowering your expectations of her, at least until you’re in a better place? If she actually hasn’t had a good night’s sleep since she was 10 and is in fact having a mental health crisis that required hospitalization, she’s not someone you want to rely on while you yourself are in a dark place. And you can’t spare the energy that would be required to approach her about this in a way that would be well-received and deal with any backlash. Who have you spoken to in the past who’s made you feel better, or at least properly heard? Call them. And don’t call your disappointing friend back until you’re feeling solid enough to be okay with or without her understanding and encouragement.

Running into dress-up trouble? Trick-or-treaters overrunning the neighborhood? Submit your questions anonymously here. (Questions may be edited for publication.)

Dear Prudence,

I do not feel I am a priority to my boyfriend. On weekends, he goes Friday and Saturday night to his mother’s to play video games with his nephew. It’s not every Friday and Saturday night, but if his nephew is there, he goes. Am I wasting my time on a 43-year-old man who would rather see family than me during our free time? He works two jobs, so we don’t have time together during the weeknights at all.

—Better Off Alone

Dear Better Off,

You’ll be wasting your time if you stay with him any longer. But don’t despair! That doesn’t mean you’ve wasted all the time you’ve spent in this “relationship.” You’ve learned something about what you want (To feel like a priority! To spend time with your partner!) and what you don’t (To take a backseat to video games and spend most of your time alone). This is important information. And if you think of it that way, you can take your newfound clarity with you when you begin dating again. I promise you’re not asking for too much. When you announce that it’s over, your boyfriend might try to make you feel like you are, though. And when he does, say “I disagree. Enjoy Saturday nights with your nephew.”

My mother is a Trump supporter. and that’s OK, I guess—I can live with that. But I think she’s been radicalized by the people or material she’s been interacting with online. She just shared a meme on Facebook that blames ethnic minorities for provoking white anger with their “baseless” claims of racism, etc., and says “we’re not going to take it anymore,” or something like that. Bad enough, but there’s a skeleton wearing a WWII German army helmet at the top of the meme, and part of the text is in a Deutsch Gothic font, which is sort of a giveaway. There’s no swastika, but the message is clear. Do I report her to Facebook for sharing racist hate material?