Dear Prudence

Help! My Ex-Boyfriend Wants to Pay Me to Go on Dates.

I feel like it’d be crazy for me to take him up on this.

One person reaches out to another, looking uncomfortable. An illustrated dollar symbol is superimposed on top.
Photo illustration by Slate. Photo by Voyagerix/iStock/Getty Images Plus. 

Our advice columnists have heard it all over the years. Each Sunday, we dive into the Dear Prudie archives and share a selection of classic letters with our readers. Join Slate Plus for even more advice columns—your first month is only $1.

Dear Prudence,

I’m a college student who, a little over a month ago, broke it off with a guy I’d been in a relationship with for 10 months. There was no spark, and I felt like being single and exploring other options. My ex is completely, unabashedly in love with me still and has been taking it really hard. He calls and texts me constantly asking for me back.

Advertisement

I’ve been broke lately, and I mentioned to him off-hand that I’m worried about funding my study abroad this summer. He then offered to pay me to go on dates with him—just a couple dates, until I leave next month. No sex, just “hanging out, the way we used to”—dinner, movies, etc. I’m not worried about the ethics of being paid for something like this (before his offer, I was considering using a get-paid-for-dates service, but I’d rather do that with someone I know); the problem is that I can’t shake the feeling that this is wrong for me to do with him and would only exacerbate things. I feel sorry for him. It seems pragmatic and makes sense in theory—he misses me, so he gets to date me, and I get money for my travels—and he’s a grown man who can make his own decisions about what’s best for him, but I feel like it’d be crazy for me to take him up on his offer. Thoughts?

Advertisement
Advertisement
Advertisement
Advertisement

I think “should I go on dates with men for money” and “should I go on dates with this man for money” are two very separate questions. Only you can answer the first, but allow me to handle the second: No. He’s already hounding you nonstop to get back together; imagine how much more of your time and attention he’ll feel entitled to once he’s paying you for your services. —Danny Lavery

From: “Help! My Ex-Boyfriend Wants to Pay Me to Just Hang Out With Him.(April 12, 2016)

Dear Prudence,

My identical twin brother had a drunken one-night stand with a woman two years ago. When asked for his name and contact the next morning, he gave my details—his idea of a joke. I looked her up on Facebook out of curiosity when she texted me, and realized she and I had a lot in common. I met up with her and eventually we became an item. I always had a nagging feeling that I should confess how we actually met. I keep putting it off, fearing her response. I want to propose to her, but feel like maybe I should come clean before we take the next giant step. I’m a fan of your column and I know you often advise people to keep mum about irrelevant sexual details that would only hurt the other partner. Does this come under such a category?

Advertisement
Advertisement

I don’t think you can say, “Will you marry me?” without also having said, “Remember that drunken one-night stand that started this romance? It turns out you were sleeping with my evil twin.” I have to assume your girlfriend knows you have a twin and that you have “introduced” her to him. So the situation you’re presenting is not a matter of keeping the details of one’s previous sexual escapades private. Instead, you and your brother are conducting a long-running farce and both of you have engaged in a level of deceit that singletons find impossible to imagine. Your girlfriend and your brother got it on one drunken evening. I don’t see how you ever feel comfortable with you and your girlfriend being around your brother if the drinks are flowing and his tongue gets loosened. Although, if he gives the best man’s toast at your wedding after having too many champagne cocktails, he could tell the crowd quite a memorable tale. You have to tell your girlfriend now with the knowledge that it could torpedo your relationship. But surely you’ve seen enough entertainment to know the twins rarely get away with their nasty tricks. —Emily Yoffe

Advertisement
Advertisement
Advertisement

From: “Help! My Girlfriend Has No Idea She First Slept With My Twin Brother.” (April 1, 2014)

Dear Prudence,

My on again/off again boyfriend of 15 years wants me to leave my husband and be with him. But he refuses to divorce his wife even though they are $50,000 in debt because of her. He refuses to help her until she helps herself. Now he’s allowing his children to make the same spending mistakes by letting his oldest go into debt for college out of state instead of making a better financial decision with an in-state college. I told him why should I leave my husband who provides for me and isn’t in debt for a person who complains about his wife all the time but never does anything about it?

Advertisement

This letter provides an exciting challenge, because I don’t believe I have an ounce of sympathy for either of you, and I’m finding it particularly difficult to wish for good things for your future. Such opportunities come rarely! It sounds like you do not wish to leave your husband for a financially insecure married man, and I suppose you have your answer there. I can’t imagine what sort of life you three would have together, if you left your partner but he stayed with his. As a longtime mistress, you have very little say in where your boyfriend’s children go to school, no matter how sound your reasoning. Something tells me they would not appreciate your financial advice. Stick with the bed you’ve made for yourself. —D.L.

Advertisement

From: “Help! My Boyfriend Wants Me to Leave My Husband for Him, but He’s Really Bad With Money.” (Aug. 15, 2016)

Dear Prudence,

My older, late-20s brother is a good-looking, athletic man who’s good with the ladies and professionally successful, which has allowed him to develop a bro-ish cocky attitude over the years. He is also an adrenaline junkie, and about a year and a half ago he suffered a serious mountain biking accident that led to losing a testicle and affected his ability to sustain an erection for a few months. Even though he healed up just fine with no impact to his testosterone level or his ability to reproduce, he has become significantly more insecure and aggressively jealous of me because, I believe, he sees me, his younger brother whom he grew up teasing, as now being more of a man than he is. At first the jealousy remained verbal when he would make snide remarks about my ability to satisfy my girlfriend. But recently, he’s adopted the practice of hitting me in the nuts by surprise whenever we’re together and then saying things like how I should be able to take it if I were a real man. It’s become so frequent that I physically stay away from my brother when we’re in the same space. I don’t want to be in pain, literally, every time I hang out with my brother but how do I tell him to stop without making him feel upset and depressed about what happened to him? It’s a sensitive topic for everyone in the family but I seem to be getting the brunt of his anger. Help!

Advertisement
Advertisement
Advertisement
Advertisement

He’s got a lot of stones for turning his anger about his half-empty sack onto you. He suffered a blow, but lucky for him evolution bestows testicles in pairs. If he is cosmetically bothered, he can explore whether he’s a candidate for a testicular prosthesis. But what he’s not allowed to do is try to smash the jewels of his baby brother in some bizarre quest for cosmic retribution. You don’t want to hang out with him because when you do, he literally takes a fist to what’s hanging. It’s time to stop letting your big bro get away with behaving like a school bully. That first means preventing him from doing you bodily harm. Have a firm, serious conversation with him in which you state he is to never—not even in supposed “jest”—touch your balls again. Follow Teddy Roosevelt’s advice to “Speak softly and carry a big stick” by having this talk while casually holding a baseball bat or golf club. If things go well and he apologizes, suggest that you guys go out and hit some other balls. If it doesn’t go well and he reaches for your crotch, you’ll be better equipped to parry his blows. This cock of the walk lost part of his set, but he should be grateful everything turned out fine (and believe me, women won’t care about this). Adverse experiences are traditionally supposed to help boy-men like your brother grow up. —E.Y.

Advertisement

From: “Help! My Brother Lost a Testicle in an Accident. Now He Won’t Stop Punching Mine.” (Aug. 13, 2015)

More from Dear Prudence

Seven years into my marriage with my ex-wife, I still wasn’t sure if I wanted kids. Eventually she stopped having sex with me—citing my indecision as her reason—and our marriage broke up two years ago. Eight months ago, I met my now-fiancee and fell in love very quickly. She’s much more sexually adventurous than my ex-wife, our moral and political beliefs are more in sync, and we’re a better fit for one another. I proposed to her on Thanksgiving shortly after learning she was pregnant. Here’s the weird thing—I’m overjoyed about her pregnancy. I can’t even explain it. Because I have many friends in common with my ex-wife, who’s still single, news reached her quickly. She immediately called me, furious and in tears. She blamed me entirely for the collapse of our marriage and said I should have told her personally about my fiancee’s pregnancy. Given how badly things ended and that we haven’t talked in two years, I disagree. Was I insensitive? Is she right to be angry with me because I’m happy about my impending fatherhood?

Advertisement