Dear Prudence


Prudie advises a sexually inexperienced woman whose boyfriend has been to orgies.

Emily Yoffe.
Emily Yoffe

Photo by Teresa Castracane.

Emily Yoffe, 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

Emily Yoffe: Good afternoon and Happy Columbus Day!

Q. Too Much Experience?: I come from a religious family—think Duggars if not quite that conservative. I was raised in an environment where sex was only for marriage, only for reproduction. I am now 30 and have had one relationship with a sexual component. That was OK but not great. About a year ago I met a great guy. He’s everything I imagine a partner for life could be. When we first started dating I explained to him that even though I wasn’t really religious anymore a lot of my upbringing still clings to me. He understood and we didn’t have a sexual relationship until we’d been dating for six months. And it was and is great! I love him not only in the bedroom but out of it too. I really think I could spend the rest of my life with him, and he says he feels the same way. The trouble? He’s very experienced sexually. Very. You name it and he’s done it—I’m talking threesomes, orgies. He never pressures me to do things I’m uncomfortable with, but I think sometimes he wishes I’d do a lot more. Right now he says he can be faithful and monogamous and I really, really want to believe him. But I can’t help but think he will eventually get bored with the same woman every single night or day, or both. Sometimes I think a lot of my appeal to him is that I’m not experienced and jaded. Should I get over it and enjoy it while it lasts and hope for the best?

A: Sometimes people have a wild past because they have an essentially wild nature, and that’s how they plan to go through life. Sometimes such people settle into happy monogamy, and can be content there because they never have to wonder, “What did I miss?” This is a guy who’s been to orgies, yet he waited six months (!) to have sex with you. He must be really crazy about you. You came to this relationship with little experience, but you’re surely learning from him that two people themselves can get pretty wild. You have brought up your fears, and he’s reassured you that he can be happy just being with you. Anyone who marries gets no guarantee that their partner, no matter what they vow, will always keep that promise. But you two have the ability to talk things out honestly, so I think you should take him at his word, and enjoy that you’ve met someone who’s opened up your world, and wants you two to make your own little world together. 

Q. Relationships: I recently started dating an incredible man who I can really see a future with—I’m in my late 20s, and he just turned 30, and we’ve been together about six months. My only concern is prior to me, he has only dated and slept with one other person—they were together for seven years and broke up about a year ago. I didn’t ask for this information, but he offered it up to me. I have no judgments about his past. My only concern is that he’ll wake up one day and wish he’d explored more, dated more people, and leave me. I on the other hand feel like I’ve had many different experiences in dating and sex, and am pretty confident in what I want. Is this a concern I should discuss with him? I don’t want him to feel as though I think it’s a deficiency, but I find myself almost holding back when I want to be in this fully because I’m afraid he’ll realize there are many options out there. He’s trustworthy, kind, intelligent, and committed, but I know that’s easier to do in the beginning of a relationship. I have an anxiety disorder to begin with so I know part of my nerves around this are fueled by that, but any advice on how to deal with what I feel is the inevitable outcome of being left to explore all the other fish in the sea?

A: And this is the flip side of the “he’s been to orgies” letter. There are some people who do not have a wild past because being wild would make them terribly self-conscious and uncomfortable. It sounds as if you’ve got a one-woman man. That can be a wonderful, reassuring thing. You don’t complain that his lack of sexual experience is putting a damper on his relationship. In fact he had a seven-year relationship, which means he likely has a lot of sexual experience, even if it’s only with one partner. You make each other happy, and he’s not interested in casual sex. That should be a source of happiness, not anxiety.

Q. Mom’s Ring: My first wife, “Lisa,” died of cancer 25 years ago, leaving me with 2-year-old twin daughters. I remarried four years later to a woman pregnant with another daughter, who I fully consider my own child, and my daughters with Lisa consider her to be their sister in all ways. Before my wife died, she said she wanted whichever of our daughters got married first to have her wedding ring. As it turns out, my youngest daughter (who is not Lisa’s) will be married in May (both the others have steady SOs but are not engaged). I think I should offer her Lisa’s wedding ring—she is the first of my daughters to get married, and I love her and think Lisa would have been happy to know that. However, my elder daughters are absolutely furious at that idea. They say they have barely anything of their mother’s and she wanted one of them to have the ring. I’m tempted to just keep the ring and not give it to any of them. What should I do?

A: Your third daughter has no attachment sentimental or otherwise to the ring left behind by the mother of your other two daughters. If your youngest had been left something by her biological father that was being held for her until adulthood, you wouldn’t suggest it go to one of your twins. Your twins have so little left of their mother—no memories and few mementos—that probably this ring has taken on outsize importance. I hope you haven’t suggested to your youngest that she get the ring, because I think you should drop that idea. And while it’s heartbreakingly understandable that your late wife wanted to project some part of herself into the lives of her daughters when they grew up, it’s problematic that this ring can only go to one. So sit down with your twins and tell them you’ve heard them loud and clear and that they are right. Say you will continue to hold the ring. But also tell them that you don’t want their mother’s bequest to become an issue between the two of them, and that the three of you have time to think about the best way to pass on their beloved mother’s ring.

Q. Worried for My Son: My son Devon is 17, and his girlfriend Mia is 15. Mia’s mom doesn’t care for Devon due to the two-year age gap. Devon will turn 18 soon, but Mia will remain 15 for some time. I believe the two of them have been fooling around and might even be having sex. My son is a respectful, compassionate, lovely young man. There is nothing predatory or coercive about his relationship with Mia. I’m terrified what Mia’s mom might do once Devon becomes a legal adult, though, especially if she discovers they had sex. I want to have a serious conversation with Devon, but I can’t find the words. Do I have cause to be worried?

A: Yes, you definitely have cause to be worried if your teenage son, who’s about to become a legal adult, is having sex with a 15-year-old. Some states have Romeo and Juliet laws precisely for this situation. That is, this clause helps prevent the boy from being prosecuted for statutory rape. But when you know the mother of a young teenage girl disapprove of her having any sexual relationship with her boyfriend, even if she is consenting, that is a situation of potentially grave jeopardy. Find the words by sitting down with your son and saying that while he may be in love with Mia, and may be totally respectful of her wishes, she is a minor and her mother does not like him. You can print out a few articles about young men who have been prosecuted for having sex under such circumstances. You can say that he may think this couldn’t possibly happen to him, but if Mia loses her virginity to him at age 15, he could be in a world of trouble. You can tell him that you truly do understand about young love and lust (you can mention Romeo and Juliet) but you also know about the world of angry parents and the law. 

Q. Re: One Ring, Two Daughters: A friend whose husband died had his wedding ring cut in half. She gave one half to each of her sons and the oldest son has now had it incorporated into his wedding ring.

A: This is a potential way both daughters can share their mother’s ring, thanks. 

Q. Girlfriend’s Pictures: My college girlfriend died about 10 years ago (I’m 45 now). Last month I got a mass email from her parents saying their basement was flooded and they lost several of their photo albums of her, including one with almost all of her college photos, so they want copies of any her old friends might have. I was just cleaning out some old boxes and I discovered that I actually have about 20 photos of her from when we were in college—but they’re not exactly what her parents might want. In every one of them, we’re either making out, at a party where she’s visibly drinking or drunk, or surrounded by (pot) smoke, and a few are pictures of her in her underwear we must have taken together (oh, the days before social media …). They’re very nice pictures of how she looked and exactly how I remembered her acting in college, but I’m not sure if it’s at all appropriate to send any of these photos to them. What do you think, Prudie?

A: I’ve dealt several times recently with a variation of this question—that is, someone has found photos of a late friend who wonders if these should be passed on to the family. I’ve heard from family members who have received such mementos of a sibling or child who died way too young, and they universally appreciate this new way to remember their loved one. Your friend’s parents have put out a call, and I think you should respond. So put the photos in a sealed envelope and write a cover letter. Explain that these are what could be considered PG-rated photos of their daughter. Say for you they bring back memories of a beautiful young woman enjoying life, love, friends, and the chance to experiment with being a little bit wild. Their daughter lived into her 30s, so her parents know this part of her youth did pass. Unless her parents are strictly religious and these photos would upset them on those grounds, they will surely be glad to have any remembrances of her happy, too short life. 

Q. Re: Worried for My Son: You should be worried. I have a friend whose son is in prison and still has a month to go on a one-year jail term—he was 18 and his girlfriend was 15 (sound familiar? Her mother called the police). Make him understand the risk.

A: Original letter writing mom, are you reading this? Have that talk now!

Q. Married Drought: I recently got married, and while most of it has been great, our sex life has suddenly gone down the tubes. Before we got married my (now) husband made me feel sexy, beautiful, and wanted. Now, I’m concerned that something is wrong. He rarely touches me, and won’t respond to my asking for or initiating sex. He instead chooses to deflect or ignore my efforts. I sat him down and asked him straight out what was wrong, and finally he said he’s been having sexual anxiety. I suggested therapy together, but he asked to work on it together, stating he didn’t trust them. I agreed but only if he could show a little progress and to talk instead of deflect or ignore me, and I agreed not to pressure him. So far he’s retreated further with no improvement in sight. I’m at a complete loss, not talking to me, no therapy, and no sex. I’m trying my hardest to be understanding and calm, but the responsible, loving man I’ve known for three years has disappeared into a withdrawn, unhappy person who if I’m honest, is more than a little selfish. What do I do?

A: You tell him that you want to be understanding, but your marriage is in jeopardy. He may have some bizarre, deep-seated terror of marriage. If so, nice that he’s letting you know by becoming celibate. If he won’t go to therapy with you, you tell him you’re going alone. I hope he can identify the source of his troubles and return to being your loving partner. But if he can’t, you will have to face that this marriage may be doomed. 

Q. Re: Ex-Girlfriend Pictures: Three words: Scan, enlarge, crop.

A: Three words: Great idea, thanks!

Q. Re: Too Much Expertise: It’s unclear from the poster’s letter if her worries that her boyfriend will become dissatisfied and stray are founded in her knowledge of his character/behavior or not. If she truly thinks he is capable of this, then she should break up with him. But I suspect her religious upbringing is influencing her worries here. Many of those strictly conservative religious communities teach that men have uncontrollable sexual desires and that it’s on women to keep men both satisfied and chaste—and it sounds like this is exactly what she’s worried about with her boyfriend. The poster’s upbringing combined with her lack of experience suggest that she may never have examined these beliefs or seen them for what they are. She may want to take these ideas out and hold them up to the light, with a counselor if necessary.

A: Good advice, thank you. 

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

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