Dear Prudence

Pay to Play

Prudie counsels a letter writer whose ex-boyfriend is offering money to hang out again.

Daniel Mallory Ortberg, aka Dear Prudence, is online weekly to chat live with readers. An edited transcript of the chat is below. (Sign up below to get Dear Prudence delivered to your inbox each week. Read Prudie’s Slate columns here. Send questions to Prudence at

Q. My broken-hearted ex wants to pay me to hang out with him: 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.

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?

A: 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.

Q. Interested in my departed friend’s husband: I’m in my 40s and have been divorced for 10 years. I’ve been happy on my own but haven’t had a great relationship in a long time. I also recently broke up with my boyfriend. About six months ago, I lost a close friend to a heart attack that was totally unexpected. I was friends with her and her husband for a long time, and losing her really hurt. Recently, her widowed husband and I attended the wedding of a co-worker. At the reception, we talked, danced together, and had a good time. I always thought he was a very handsome and nice man and that my friend was lucky to have him. Knowing what kind of a man he is, I’d like to pursue a relationship with him. I know he may not be ready after six months, but I’m available when he is. Some at work saw how we interacted at the reception and have started saying that I’m a “vulture” for being interested in him, and someone else thought I wanted to sneak around with him while he was still my friend’s husband, which is not true. This man is no longer married, and I think he’s a great catch for someone my age. Is it wrong for me to be interested?

A: It’s not wrong to be interested, but it would be wrong to push for anything if he wasn’t giving out very clear signals about being ready to date again. You’ve been divorced for 10 years, so it’s understandable that you’re eager to date someone you know well and feel strongly about, but he’s only been widowed for half a year. Let him take the lead—don’t start dropping hints that whenever he’s “done” grieving, you’d like to go out.

Q. The work of love: I have an unusual job: I’m a sex worker. Lately I’ve been dating a lot, and while I haven’t really gotten to this point in a relationship yet, I’m wondering when I should tell my dates and potential sexual partners about my job. Do I have an ethical obligation to tell my partners before we have sex? I am always safe with my clients, and, frankly, I don’t really consider selling sex to be any different from providing any other service. At what point in a relationship should I tell someone that I am an escort?

A: You don’t, I think, have an ethical obligation to tell your partners what you do for a living before you sleep together, especially since you’re practicing safe sex and not putting anyone at risk. My only advice would be that it might save you some wasted time by being up-front about your job—you presumably wouldn’t want to date anyone who stereotypes or resents sex workers, and this might help screen those people out. Of course, I also understand that disclosing your work puts you at some risk of arrest or violence, so I don’t want to encourage you to disclose before you feel comfortable. The short answer is: Whenever you feel ready to tell someone you work as an escort is the right time. Happy dating!

Q. One or none?: I am a 32-year-old woman engaged to the father of my 3-year-old. Our relationship has been up and down, but we both agree that we are a good fit for each other. Until, at least, I met a man I fell hard for. He and I have similar interests and talents, and he’s dealt with the same anxiety and depression disorders. There is something between this man and me that will never be fully realized, and I acknowledge that, but I feel like my relationship with my fiancé is faltering. Our relationship feels like a safe bet, and the fighting and bickering is worsening. He has been through my text messages and emails because he feels “something’s going on.” I’m debating leaving, but that would mean I and my son would be moving out of state (back to my hometown, about three hours away). I feel crazy, but I think I’d rather be alone than in a relationship with a man I don’t feel, well, in love with. Is this what all long-term relationships end up like?

A: In reverse order: No, all long-term relationships don’t end up like this; you can leave if you want; your relationship is faltering (not just “feeling like” faltering) because you have been having an emotional affair with someone whose most prominent characteristics appear to be “good at the things I’m good at” and “has a similar depressive disorder.” You acknowledge there’s no future with this other man. Consider that at least one of the reasons you no longer feel in love with your fiancé is because you have been investing all of your emotional and romantic energies in someone else. This relationship has not suddenly and mysteriously deteriorated; there is a very clear cause and effect. You fell for someone else, removed your romantic attention from your fiancé, and he grew clingy and insecure as a result.

Consider that it’s possible you two would fight and bicker less (or could at least fight better; not-fighting is not always the highest good) if you acknowledged he is not being paranoid about “something going on” and were honest about your feelings. I don’t know if this relationship is salvageable, but for the sake of a good co-parenting relationship, consider all of your options (couples counseling, living separately but in the same city, etc.) before moving out of state with your 3-year-old son.

Q. Betray dad by telling mom about his cancer?: My parents are divorced and aren’t on speaking terms. My dad has asked my brothers and I to keep his cancer a secret from my mom. We haven’t told her, but it’s been hard not being able to go to her for support. In a few weeks, they will both be at a big event, and I think my mom will find out about the cancer when she sees him. I don’t want her to be blindsided, but I don’t want to betray my dad’s trust. What should I do?

A: Talk to your father. Tell him your mother is going to put two and two together the next time she sees him, and it will be better for her to be prepared in private than for her to come to a sudden realization in public. If he’s still insistent, I think you should respect his wishes, but hopefully you can help him understand this will protect him from a possibly painful and upsetting public outburst.

Q. Selfish motives: I have dreamed of the day I would become a mother for as long as I can remember. I adore children and have chosen a profession where I can provide care for sick babies and young children, which fills my heart and gives me a sense of purpose. In my mid-20s, an abusive situation finally opened my eyes to leave the cult I was raised in. Consequently, my entire family and every friend I had ever known now pretends I am dead. I moved to a small town where no one knew me and am now married to the love of my life and am planning a family with my husband. The problem? I am having severe anxiety over the idea of having kids. We have no family close by (as my husband was new to the area too) and only a very small circle of friends in distant towns at least an hour away. I can’t imagine raising children that don’t have a support network other than their own two parents. I don’t want my children to feel secluded or cut off from the rest of the world like I was, but I have nothing to offer them to the contrary. I can’t imagine my life without children though. Am I being selfish for wanting to have children so I can finally feel like I have a real family again? My husband is very supportive either way and says family is what we make of it.

A: You are not being selfish—you have been deeply hurt. I’m so sorry that at some point in your life someone told you that “having emotional needs” and “being selfish” were one and the same. Lots of children grow up in small towns with few relatives. That doesn’t mean they don’t experience love and intimacy and joy like everybody else does. Your children will develop a social network as they grow up and make friends in school, and you will too, as you meet other parents with children your age. Your children will not be cut off from the world in the same way you were, because you’re not going to raise them in a cult or pretend they are dead when they do something you don’t like. You sound thoughtful and sensitive and deeply caring; I think you will make a wonderful mother.

Q. Can I tell my boyfriend his hair looks bad?: My boyfriend is a great guy—extremely helpful and loving, reliable, and supportive. Easily the best guy I have ever been with. We’ve been dating about four months now. My problem seems silly: For every special occasion (wedding, fancy dinner, meeting family, interview, etc.), he styles his hair in a way that is incredibly unflattering. When he does nothing to his hair beyond washing and drying, it looks great—really nice, actually. Which makes it all the more frustrating that he insists on messing with it. It ends up looking wet and leaving stringy tendrils curling over his forehead. I’ve tried praising his hair without product a ton—letting him know it really looks great that way. I’m afraid I need to be more clear about the fixed ’do, but I’m wondering if that crosses a line. I don’t want to criticize someone that is just about perfect in my book, but I also don’t want him going around looking like a character from Grease. What should I do?

A: How many special occasions have come up in just four months that this is a significant problem? Tell the man you don’t like his hair styled that way. Maybe he’ll take your input and try something different; maybe he’ll laugh it off and tell you he loves his Teddy-Boy pompadour, and you’ll have to learn to deal with it.

Daniel Mallory Ortberg: Let’s keep it light next week, friends. I’m going to give my dog an extra treat today.

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If you missed Part 1 of this week’s chat, click here to read it.