Dear Prudence

Help! I Can’t Stop Having Deep Conversations With My 19-Year-Old Student.

I don’t even talk like this with my husband.

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Photo illustration by Slate. Photos by OSTILL/iStock/Getty Images Plus and CarlosDavid.org/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 am a 30-year-old married college teacher and a mother. I have recently developed a platonic relationship with one of my students. He is 19 years old and is quite smart and intelligent for his age. We chat, through Facebook mostly, about topics related to what I teach (philosophy, history, literature, current events) and we seem to have connected intellectually in many aspects. I have conversations with him I don’t even have with my husband and it has been very mentally stimulating. I find myself feeling guilty about this relationship, as if I were cheating on my husband because I found someone that fulfills something in me that he doesn’t. I consider myself a woman of morality and integrity, but I am also frightened that this might develop into something else if the boundaries are blurry. Am I wrong for having this relationship?

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As an expert in the humanities, you are probably familiar with this saying by Blaise Pascal: “The heart has its reasons which reason knows not.” (This was famously paraphrased by Woody Allen to explain his affair with Mia Farrow’s daughter.) So once you’re in the territory of knowing you’re in a morally ambiguous relationship, professor, you also know the answer is, Cut it out. Right now you are connecting intellectually with this young man. Given the porousness of your emotions, you are already worried about finding yourself connecting on so many more levels. I am not in any way saying that a professor and student can’t have a wonderful, intellectual relationship that extends outside the classroom. The world would be so much poorer if there were no professors able to be mentors to students of the opposite sex. But it does mean that when you’re thinking, “This relationship is so much more fulfilling than my marriage,” that you are jeopardizing your very standing as a professional. Cut out the Facebook chats and start reeling this in. At the end of this term recommend classes for this young man to take the next academic year that will enhance his academic journey. Keep in mind that you don’t want to do anything that will bring your academic journey to an end. —Emily Yoffe

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From: “Help! I’m Having an Intellectual Affair With My Student.” (Feb. 19, 2014)

Dear Prudence,

My boyfriend, who I love very much, underwent treatment for cancer a few years before I met him (he’s thankfully healthy now). We’ve talked about marriage and children, but we’ve run into a major problem. His treatments left him unable to have kids. He froze a sperm sample before his treatment, but the problem is that the sample is only viable for a few more years. I love this man, and I want to marry him and have kids with him, but this ticking clock means I would have to try to have a kid in the middle of medical school! And there is of course the chance that it may not work. For religious reasons, adoption is not an option, and neither is sperm donation or similar recourse. I never wanted to have kids until after I finished school, and the prospect of this being our only chance is terrifying. But I also have a more selfish desire that’s leaving me feeling so guilty—I always pictured having a larger family, at least three kids, that kind of thing. I know it’s unreasonable to have a set view of what I want my life to look like, but I just know that I want multiple children. And I don’t think I can have that with my boyfriend, and that is deeply saddening. I’ve read many indignant responses to Prudence letters about people who married without agreeing on a major deal-breaker like kids, and I feel horrible for considering this, but do I need to be thinking about ending this relationship? I don’t want to! But I don’t want to wake up one day resenting him because of this. He doesn’t deserve that. I feel so hopelessly stuck, because I want to spend my life with him, and I don’t want to put us both through pain later on. Help!

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I think that it’s a great idea to have honest conversations about children before getting married. I also think it’s impossible to promise someone, “What I want right now will never change, and as long as I promise you I do (or don’t) want a child (or a specific number of children) before we get married, we will never have to experience fear, anxiety, uncertainty, or the pain of not getting what we want, when we want it.” My inclination is to discourage you from trying to get pregnant now just because you’re afraid of the future—a scarcity mindset is not a welcoming environment for children, and it’s better to err on the side of caution when it comes to bringing new life into the world, but that’s not to say that you can’t consider it.

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The best thing that you and your boyfriend can do right now is to honestly discuss your options, your hopes, and your fears. Tell him what kind of family you want to have. If you are frustrated that adoption or sperm donation is not an option, say so. If you feel that you could be a good parent at a different time in your life but that you could not be one right now, acknowledge it. Tell him what your worst-case scenario would be. Would it be losing him over this? Would it be having children in a hurry right now because you felt like this was your only chance, then coming to regret it, and resenting your husband for it? What does his worst-case fear look like? Where do you two differ? Where do you two connect? This needs to be the first of many conversations, not the last. It may be that you two simply cannot compromise on this point, and a breakup will be inevitable, but you have a lot of other options to explore before calling it quits. You may find more points of connection than you can see at present. —Danny M. Lavery

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From: “Help! I’m Not Ready for Kids, but My Now-Infertile Boyfriend’s Frozen Sperm Will Expire Soon.” (Nov. 7, 2016)

Dear Prudence,

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?

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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. —E.Y.

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From: “Help! I’ve Had Little Sexual Experience, but My Boyfriend’s Had a Lot. Like, Orgies.” (Oct. 12, 2015)

Dear Prudence,

My 90-year-old grandmother is very ill and will die in a matter of weeks. We’ve always been really close, as I’m her only granddaughter and my mother was her only daughter. When I was looking for some old photographs to look through with her in her attic, I stumbled upon letters written when she was in her 20s. It was a love note, to a woman, with a reciprocation from that woman as well. Some more framed pictures of the woman were also stored (with her name on them). I know my grandparents had a strained and cold marriage, although I never suspected my grandmother’s sexuality might have been a reason for that. Now, I’m not sure if I should show her the letter and pictures, because it might make her remember her happiness when she was with that woman, or whether it would upset and embarrass her (she’s pretty buttoned-up). My mother has passed away, so I can’t ask her for advice. What do you think?

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I think when a 90-year-old woman is weeks away from dying, it’s generally not a good time to ask if she wants to come out. She was once in love with another woman and had fond enough memories to keep a few letters and photos of the two of them; that doesn’t necessarily mean this woman was the love of her life, or the reason her marriage to your grandfather was so strained. I think you can split the difference: If she’s lucid enough, the next time you speak to her, you can tell her you went through the attic and found a lot of old photos and letters, and ask if there is anything she would like to look through again. If she seems interested in a walk down memory lane, you can bring the letters along with whatever else she asks for; if she doesn’t, don’t cause her distress by forcing the issue. The key question to ask yourself before acting is is: Do I think this would comfort and bring solace to my dying grandmother, or do I think it would satisfy my own curiosity about a closed-off woman’s personal life? While the latter impulse is understandable (I’m nosy too), it should not dictate your actions. —D.L.

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From: “Help! Should I Tell My Dying Grandmother I Know She Once Loved Another Woman?” (Dec. 6, 2016)

More from Dear Prudence

Several months ago, I met a nice man at a gathering of friends. We hit it off and started dating. He’s smart, funny, and sweet. He clearly adores me, and I’m starting to feel the same about him. We are both well over 40 years old. On a whim, I Googled his name and found a news article, with a photo of him, describing his arrest several years ago on a charge of soliciting a young teenage girl over the Internet for sex. There was no mention of the outcome of the case, and he’s not listed on a sex offender registry anywhere. He is divorced and his son lives with his mother. I have no children. The physical part of the relationship has been great, and he seems extremely happy to be with nonteenage me. Do I bring this up or keep it in the past, where he seems to want it? Should I out him to our friends, none of whom have young children? How do I (or should I) unlearn what I found out about this otherwise wonderful man?

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