Dear Prudence: Being a sugar baby helped me pay for college. Does my fiance deserve to know?

Help! I Paid for College by Being a Sugar Baby. Should I Keep This a Secret?

Help! I Paid for College by Being a Sugar Baby. Should I Keep This a Secret?

Advice on manners and morals.
Sept. 24 2012 2:50 PM

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.