Dear Prudence

My Life as a Sugar Baby

In a live chat, Prudie advises a woman on whether to stay mum about having dated rich men for money.

Emily Yoffe.

Emily Yoffe

Photograph by Teresa Castracane.

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

Emily Yoffe: Good afternoon, I look forward to your questions.

Q. Tell Fiancé I Used To Be a Sugar Baby?: I have an odd question today. For a few years I was a professional sugar baby. I had at least four sugar daddies at one time (I did NOT sleep with them or do anything of a sexual nature.) I was simply a companion, a travel and dinner date, and someone to confide in. Through this I was able to get through school and purchase my own house with the money I made. My problem is do I tell my fiancé about my past or should I tell him I just dated a wealthy man? I don’t want him to think of me as a gold digger!

A: You must be a hell of a conversationalist. Are there that many rich men who complain, “All my wife wants to do is have sex with me, but she doesn’t listen when I take her out to dinner?” I believe that when entering a new relationship one doesn’t have to disclose all past sexual encounters, but that you do owe your new love information that’s relevant. That includes such things as STD status, or having slept with your boyfriend’s brother. Your question is not about sex, but money. But if you’ve engaged in professional activities that you would be too embarrassed to tell your beloved, then you probably should tell because you surely don’t want someone else to tell. I’m assuming some friends of yours must have known how you managed to avoid student debt. Since you got engaged, you’ve waited a rather long time to reveal how you put yourself through college. I think you should tell your fiancé that for several years you went out with a series of rich men who helped support you but with whom you didn’t have sex. If he asks you direct questions, answer them honestly. He may find this hard to believe, he may be repulsed, he may admire your entrepreneurial spirit. But you don’t want to be worried that someone else will mention to him the real reason you could afford that down payment.

Dear Prudence: Excessive Family PDA

Q. Friend Teased My Child: After my newborn and I were discharged from hospital, she had to be rehospitalized for some minor health concerns. Due to circumstances, my husband couldn’t care for our older daughter, so we asked a close, trusted family friend to look after her for three days. After our baby came back home my older child became completely disruptive, jealous, and demanding. She was fine before so I had no idea why she suddenly disliked the new baby. After some gentle probing we discovered our friend thought it would be hilarious to tell our child that mommy and daddy didn’t want her anymore. And that’s why we had a new baby—to replace her. It sounds as though the friend drummed the story into her over and over judging by my daughter’s reaction. My daughter has a lower cognitive ability than mainstream children. So for her to be this upset, our friend would have had to repeat the story several times. My friend likes to kid around and tease my daughter which was always within the limits of good-natured fun. But this really crossed the line. I am livid that she thought it was funny to cause my child distress. I’ve refrained myself from speaking to her about this because I don’t trust what might come out of my mouth. What should I say to her?

A: I’m assuming your young child to the best of her ability is reporting what your friend actually said. If so, then your friend has rocks for a brain and a heart. But first of all, you’ve got to get your friend’s version. Bear in mind, even the most seemingly loving and mature older brother or sister has been known to become a snarling dog once realizing that this adorable new baby is here for keeps. So sit down with your friend and say you appreciate her stepping up during your emergency. Then explain that Marissa’s adjustment to her new sister has recently been particularly difficult and you’d like to know what the friend said to her about the new baby. If your friend says she gave Marissa the standard pablum about how exciting it is to be a big sister, then you have to say Marissa must really have misunderstood. Say she reported that you that you told her she was being replaced. You understand this would have been teasingly, but that for the sake of your daughter’s psychological health it’s really important you know what was said. If she owns up then say to her you’d like her to apologize to Marissa and explain what she said wasn’t true, it was just a very bad joke. When that’s done you can privately say to her that you are deeply wounded that she would tell a vulnerable girl something so terrible and you hope she sees the distress she’s caused all of you. I don’t see how you go on with a friendship with someone so lacking in judgment.

Q. Re: sugar baby: About a year ago, my wife told me that she had been a “sugar baby” in college. FWIW, it was painful for me to hear but everyone has done things that are not proud of. And after a few months of counseling, everything is back to normal. I would recommend that everyone be upfront and honest about these things.

A: Thank you. It’s always so helpful to hear from someone else who has been there.

Q. Dating My Former Student: I am dating a former high-school student and have been for some time. I love her and did not become involved with her until she was in her mid-20s. We didn’t even see each other for five years after her graduation. I know we did everything morally and have nothing about which we should be ashamed. That said, I still hesitate to introduce her to my colleagues, who also taught her, as my girlfriend. I worry I will come off as a pervert or that they will judge me for dating a former student. My girlfriend has introduced me to many of her friends and her family, and I have not done the same, because many of my good friends are teachers, and I’m a little embarrassed to admit I fell for a former student. If I want to keep my girlfriend, and I really want to keep her, I need to get over my ridiculous embarrassment. Do you have any suggestions about how I could introduce my girlfriend without making our former relationship the center of the introduction?

A: You introduce her and then the two of then tell your delightful story about reconnecting. She says something like, “I was getting popcorn at the movie theater last year when I saw Dan ordering Rasinettes. I even said, ‘Hey Mr. Miller,’ it’s Courtney Simmons.” Then you say at first you didn’t recognize her, it had been years since you’d seen her. But you started talking and sparks flew. By doing this you charmingly answer all the questions that are forming in the minds of your colleagues and you are reassuring everyone that this relationship didn’t start until Courtney was long out of school and an adult. Remember that if you act and feel guilty, that will send the subliminal message that there actually is a dirty little secret to this romance. There isn’t, so be glad Courtney’s yearbook is gathering dust and that you have found each other.

Q. Pets Aren’t Children?: I do not have children of my own, so my pets have become my children. I love each and every one of them as much as my friends with children love their kids. Last week a neighbor’s dog attacked and killed one of my beloved cats. My deceased cat was only 4-years-old and was sweet and funny and feisty. I feel raw grief and emptiness over losing her, especially so violently. Four years ago my good friend Claire lost her daughter in a drunk driving accident. (Claire’s daughter was the drunk driver.) I told Claire I understood how she felt about losing her daughter so horrifically. Claire flew into a fury and raged at me, calling me crazy for equating the loss of her child to the loss of my pet. I know many people wouldn’t agree that pets can be children, but I didn’t mean any harm by my comment. I wanted Claire to know I was feeling pain like she had and that we could support each other. What should I do to repair our friendship?

A: Write her a letter apologizing. Say that out of your own sadness you made a horribly insensitive remark which you deeply regret. Say your heart breaks at the loss of Claire and you never meant to denigrate the pain your friend will always feel. Say you hope she can forgive your blunder.

Q. “Sugar Baby”: This is a real thing? Why didn’t anybody tell me? I was a cute girl in my 20s. I could have done that. Instead I just worked. What a sucker I was.

A: Lots of women are writing in about how they wish they’d known there was an easier way to finance that law school education. Sure, there must be rich men willing to pay for the company of an attractive woman. But my impression is that rich men don’t tend to have trouble finding such people without drawing up contracts. Of course, one celebrity (can’t remember who) who got caught up in a prostitution scandal explained there was a reason he paid when so many women would do it for free: “You aren’t paying for the sex. You’re paying for them to leave.”

Q. Was Happy To Be “Just Friends”: During the rough times of my recent divorce, a woman friend of mine provided great support. We’d been friends for many years. Never anything untoward (she wasn’t the reason for the divorce). We became even better friends. After the dust settled, I let her know that I was attracted to her and would she like to take the relationship “to the next level”? She let me know, kindly but unequivocally, that she did not want to go there. I accepted that and was happy to continue being “just friends.” We continued to have dinner or go out to events together. Fast forward a few months, and I’ve met a woman whom I care for deeply. New girlfriend is even happy to know that I have a woman as a “best friend.” However, suddenly my “best friend” stopped talking to me and shunned me at social gatherings. I was sad, but ready to move on. Now she is telling stories on her blog (which is read by many mutual friends) that I walked away from her because I was unhappy that she wouldn’t be my girlfriend—far from the truth—and included disparaging remarks about my new girlfriend. How do I respond to this?

A: She didn’t want you, but she didn’t want anyone else to want you, either. Since you were friends (I’m deliberately using the past tense), ask her to go out to dinner. Say that you’ve seen the things she’s posted on the blog and they are both hurtful and untrue. Add that if she was unhappy with you in some way, you wish she’d come to you instead of blasting it publicly and request that she stop. I’m hoping your mutual friends not only have better things to do than read this blog. I also assume they will find her nasty invective disturbing and odd. You could also mention to a few reliably chatty people how disturbing this incident has been. You accepted that Maria was not interested in you romantically, but you can’t believe that she would insult a lovely person she doesn’t even know who is.

Q. Brockovich Syndrome: My business partner (we are equal partners) is an attractive, fit woman in her 40s. She has a not-so-conservative taste in clothes, but since our office is tilted toward casual wear, that doesn’t cause issues there. Lately, though, when we go outside for business meetings, her manner of dress is what I would call “club wear:” high and low cut dresses revealing lots of thigh and cleavage combined with “stripper heels.” Last Friday we met for a possible contract with execs from a professional firm, and my partner dressed in such an over-the-top revealing style that it distracted the meeting badly. I had a call this morning from their spokesman asking me to supply additional credentials. I’m sure it’s because they thought we purposely distracted them with her to deflect from the deal’s details. I have never addressed this issue with her, and I need some guidance.

A: You’re a businessperson who goes out and sells your work to potential clients. This takes a lot of cool and confidence, so surely you can apply those same skills to telling your partner that her attire is distracting from your presentations. You don’t have any evidence that the recent call was a result of your partner’s clothing, but if she made you uncomfortable surely everyone else was, too. Suggest she go to one of the major department stores and get the services of a personal shopper so that she can start building a professional wardrobe that doesn’t send mixed signals.

Click here to read Part 2 of this week’s chat.

Discuss this column with Emily Yoffe on her Facebook page.

In a new approach, we’re publishing the chat transcript in shorter, more digestible pieces. You will still be getting all the questions and answers, and we may even publish bonus letters Prudie didn’t get to address during the chat hour.