Dear Prudence

Help! My 30-Year-Old Boyfriend Has No Interest in Losing His Virginity.

It’s gonna be tough long term, but I’m hesitant to pass up an otherwise great guy.

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Photo illustration by Slate. Photo by twinsterphoto/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 have been seeing a really sweet guy for three months. He is intelligent, fun, considerate, and generous. My issue is that he is a virgin and doesn’t seem very interested in changing that. We are both in our early 30s. I am recently divorced—my husband was a compulsive cheat—and have a 2-year-old son. I have discussed sex with “James” and he said that he originally wanted to wait until marriage for religious reasons, but now doesn’t feel that is necessary, he just wants it to be with the right person. We were making out the other night and I whispered to him how much I wanted him. He said he wanted me, too, but he sounded awkward and unconvincing. He always tells me that we can’t do anything because he doesn’t have condoms, but he hasn’t made any attempts to purchase some. I can tell he is aroused when we kiss, but I’m worried that he just isn’t very interested in sex. That would be tough for me to handle long term. Is it wrong that I expect our relationship to be further along after three months? My friends say I need a man with more heat and passion but I am hesitant to pass up an otherwise great guy.

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“I don’t have a condom” is “The dog ate my homework” of the lifetime virgin. You say you’re worried he’s not interested in sex. Since he’s never had it, despite your giving him the opportunity, you may be onto something. Of course, it’s possible he is interested in sex but, having gotten to this point in life without knowing what to do, he may be terrified about disappointing a sophisticated woman like you. It could be that he has some kind of sexual hang-up, or feels self-conscious about his body for some reason. But here he is, with a knowledgeable partner eager to get him over the hump, and he keeps balking. You have just been deeply hurt by the man you thought you would spend your life with, and I understand there is not an abundance of lovely, eligible men. But having a partner you’re certain will never cheat on you because he’s apparently incapable of doing the deed is not the answer. You also must know that even if you do get him in bed, it’s likely to be a frustrating experience. See the hilarious consummation scene at the end of The 40-Year-Old Virgin. I believe in the value of going slow, but three months is long enough to see if a relationship is worth investing more time; one way to find out is to explore your sexual compatibility. If you’re willing to lead the guy by the hand, then have a discussion with him explaining you think it’s time, and you will purchase the condoms. If you two still can’t get into bed, that’s evidence enough your relationship won’t survive outside it. —Emily Yoffe

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From: “Help! My Boyfriend Is a 30-Year-Old Virgin.” (Oct. 24, 2013)

Dear Prudence,

I recently moved to a new state for school and became friends with a heterosexual man who seemed comfortable with the fact that I’m a lesbian. Lately, though, he’s been making repeated comments about how much we have in common, that we should be each other’s “wingman” while dating, and how we “really have to” stop doing things together that might make us seem like a couple. I don’t think we do very much that’s couple-y—we were part of a shared group Halloween costume and occasionally go grocery shopping together (always at his suggestion, which usually means we split up at the door and meet back up in the parking lot half an hour later). Normally I wouldn’t think much of this, but he also keeps bringing up “date ideas,” and two days after he described his ideal date to me, he texted to ask if I wanted to do that exact thing together. I turned him down and have avoided hanging out one-on-one with him since. Not only that, I’ve also told him I’m not interested in dating right now and have no intentions of being or needing a wingwoman. Part of me is still worried he might be forming a romantic attachment. Am I just full of myself and reading too far into things? If you share my suspicions, how can I make him back off when I’ve already spelled out the fact that this is never going to happen?

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I just had the worst Chasing Amy flashback of my entire life. I am going to make a blanket statement: People are generally not as good as hiding their unrequited affections as they think they are. Yeah, this guy sounds like he’s forming a romantic attachment to you and trying (and failing!) to be subtle about it. I don’t think you’re too full of yourself or reading into something that’s not there. That said, I think you’ve already done everything you can, given your current parameters—you told him you’re gay, that you don’t want a wingman, you’ve turned down his offers of a nondate-date, and you’re not planning on spending any solo time together anymore. If he’s remotely self-aware, he’ll pick up on your increased distance and won’t spend (much) time offering to go grocery shopping together anymore. If he does persist, then you can get a bit firmer in turning him down. —Danny M. Lavery

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From: “Help! A Straight Guy Friend Knows I’m a Lesbian but Keeps Bringing Up “Date Ideas.” (Nov. 28, 2016)

Dear Prudence,

I love to travel, and really enjoy getting away for the weekend whenever possible. However, my boyfriend of four years has put a real damper on this for me. He seems obsessed with the idea of my flashing truckers when we are on the road. He will pull up beside an 18-wheeler and slow down, expecting me to show off the goods. This makes me very uncomfortable. When I refuse, it turns into a huge fight and he ends up not speaking to me for days. He claims that he does so much for me every day and he can’t understand why I can’t do this thing for him. It has caused a lot of ridiculous fights between us. What can I do?

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I like Dan Savage’s formulation that people in sexual relationships should be GGG—Good, Giving, and Game. That is, good in bed, generous sexually, and open to exploring the corners of their beloved’s erotic life. However, if being GGG on a road trip means you end up as road kill, then it’s time to bow out of engaging in your boyfriend’s fantasies. It doesn’t matter if on a daily basis your boyfriend cooks you Michelin-worthy meals and then massages your feet. He gets turned on by your exposing yourself to strangers driving a rig who if they get distracted could squash you like a bug. The answer to your boyfriend’s request is very firm, “No.” If that causes him to stop speaking to you, then you need to extend the silence to forever because he’s simply a creep. —EY

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From: “Help! My Boyfriend Demands That I Flash My Breasts at Truckers.” (Sept. 30, 2014)

Dear Prudence,

This summer, I dated a guy I met through our internship program for a few months. The relationship was very intense, but we live on different sides of the country, and I broke things off a few weeks after we left because I wasn’t ready for a long-term, long-distance commitment. A few months later, he called me out of the blue and told me he’d gotten a serious medical diagnosis, and wanted to bring up our past relationship. I’d been missing him and felt terrible for him, so I promised to visit and talked about the future with him.

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A week into our reconnection, he started getting possessive and irritated that I wasn’t spending enough time talking to him. He’d say things like I was the only thing in his life worth fighting for, and I had to tell him that while I cared for him, he was making me feel uncomfortable; he responded by telling me that he had lied about the original diagnosis and that it was much worse and he didn’t “have much time left.” I honestly did not know what to think of this, and perhaps in shock, I canceled my plans to see him and haven’t spoken to him since. I feel guilty, that regardless of our past relationship, simply because I care about him as a person, I owe him some measure of compassion in this really messed-up place in his life. I also feel ashamed that I’m being selfish, that I don’t want to accept the responsibility of being there for him as he dies. I want to reach out and apologize for overreacting, but I also don’t want to be subject to a situation where he expects me to be an emotional crutch from the other side of the country. I don’t really know what the right answer here is.

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There is nothing selfish about refusing to be this man’s emotional hostage. I believe him when he says he lied about the initial diagnosis, but not that he initially downplayed the seriousness of it—my guess is he’s not sick at all. I think he invented a diagnosis to get your attention (it’s already odd that he called up a summer fling and declared she’s his only raison d’être), and when that wasn’t enough to convince you to devote your entire life to him, he announced that he was on the verge of death in order to get what he wanted. He has behaved manipulatively and dishonestly, and I don’t think you should trust him for a minute.

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Even if he is ill, that would not be sufficient cause for him to tell a girl he dated for two months that she’s responsible for keeping him alive. Showing someone compassion does not mean you have to give in to their every demand, and the fact that he expected you to spend every minute talking to or thinking about him is frightening. His controlling behavior bears hallmarks of escalating emotional abuse, and illness or no, he has no right to make you responsible for his well-being. If he is sick, it would be better for him to get support from the people near him who are already part of his life. If he made up this story (and then made it sound worse when Phase 1 didn’t work on you), then the best thing you can do for him, and yourself, is to block his number. Do not apologize and do not reach out to him. —DL

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From: “Help! A Guy I Dated Says I Have to Be With Him Because He’s Dying.” (Nov. 3, 2016)

More from Dear Prudence

My boyfriend of two years says that he will not ask me to marry him unless I take a lie detector test to pinpoint the truth about certain things that have gone on in our relationship. I have been faithful and honest to him throughout the time we have been dating, with the exception of getting caught in some white lies about things that occurred before we were together. He says that if I have lied about little things, then I could lie about big things, and he needs to know he can trust me. I’ve always been of the mind-set that what happened before you were with your partner is not really their business and doesn’t affect the relationship. I refuse under any circumstances to take the test. I’ve made sacrifices and compromises to keep him happy, but his request is completely unreasonable, isn’t it? Is it a sign of overall problems? What should I do?

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