Dear Prudence: I'm 25 and have never been kissed.

The letters for this week's archival Dear Prudie column are pulled from Dear Prudence: Liberating Lessons From Slate.com's Beloved Advice Column by Danny M. Lavery. For more of the most sensational letters from Danny's tenure, buy the Dear Prudence book here.

Dear Prudence,

I am a 25-year-old woman, and I have never really had a romantic relationship. I had a crush in high school that didn't work out. I went to a college with a significant gender disparity, and it seemed like all my friends got asked out by the few men who attended, just not me. I seemed invisible. I ended up dropping out of that college due to family issues, moved back home for a year, and worked. My parents had moved away from my hometown at that point, so there was no one there I could reconnect with. Still, I managed to make friends. But my romantic life went nowhere. One guy asked me out, but he was a known creep I had been warned against. Another guy was younger than me by nearly four years.

Embarrassingly, I’ve never even been kissed. I feel like something is wrong with me. I’m still in touch with my friends from high school and college, so it's not like I can't connect with people. Yet no guy has ever been interested in me. Is it my looks? I’ve been told by a guy friend that I’m a "6.5 out of 10." I’ve always been the plain Jane of my friend groups. But I’ve always made sure that I have been presentable. Is it my personality? A lot of my girl friends say that I am confident and cool to be around, and they’re always in disbelief whenever I mention my lack of romantic connections. A few of my guy friends have mentioned that they also think I’m cool, but men have trouble liking me since all of my friends are "nicer" to be around. According to them, even though I am caring and personable, I’m still too assertive and dominating. One guy even said that I’m too loud and needed to be quieter. At this point, I don't know what to do. I know that there's something wrong with me. There has to be. I have been told over and over that I don't need to be in a relationship until I’m ready, but I have been ready for years now.

I know that the obvious solution is to put myself out there and try dating apps, but I feel like at this point, if no one has ever liked me, then no one ever will. I feel embarrassed by my lack of experience and with every year, it only gets worse. I feel like I would have to lie to whatever future dates I have about my history just so they don't think I’m pathetic or start looking for flaws that would have repulsed others. Plus, all of my friends in relationships have met their partners organically. I’m jealous that someone could meet them on the street, or in school, or in a club and immediately be interested in them; meanwhile, I’m an acquired taste at best. Any advice would be helpful.

There's a complicated mix of genuine self-respect and deep despair in your letter. I’d like to start by encouraging you never to ask your male friends to "rate" you again or to attempt to speak on behalf of all men about why you either are or aren't categorically worth dating. Those friends are not capable of speaking on behalf of all men, and you yourself are already aware that their "advice" is chaotic, sometimes contradictory, and not worth following. I can't help but notice you don't say much about whether you think these friends are people you’re interested in dating. You don't say anything about what men you might like to date, aside from the brief acknowledgment of a crush in high school. What do you want out of dating aside from external validation that you are "worth" dating? (External validation is a perfectly fine thing to want; I’m not suggesting you should only date out of elevated ideals and principles, but there ought to be something more to what you’re looking for.) What do you want to get out of dating beyond a checkmark that announces to the world, "Some man—any man—considers me worth dating"? What do you desire in a partner? What interests you? What catches your attention? What do you long for? What do you seek to protect and safeguard and cherish? How do you want to display your interests and affection to others?

You feel embarrassed and disgusted with yourself because you believe no man has ever wanted to go out with you, but that's not quite true. I don't say this in the spirit of argument, but because I think it speaks to your state of mind that at present you seem unable to acknowledge information that doesn't validate your self-loathing. I can understand perfectly why you might not have wanted to go out with those two men, but the fact remains that they very much did express an interest in you. You concede that trying dating apps is "the obvious solution" but then dismiss it by claiming that it would somehow be insincere or fraudulent in comparison with your friends who met their boyfriends in class or at a bar. It seems to me that you have assembled a series of elaborate beliefs, touchstones, and rituals that serve as both self-protection and self-harm, and I fear that asking you to be kinder to yourself will come across as flimsy or out-of-touch. But I am certain that mentally beating yourself up and establishing a series of rules that "prove" you’re a lost romantic cause will do you no good. You do not have to set up profiles on dating apps if the idea causes you too much pain, although I hope you will consider taking a calculated risk on that front. You do not have to pretend to enjoy being single if you would prefer to be in a relationship. But I think it will do you a world of good to stop treating your male friends as romantic authorities when they have merely proven themselves eager to criticize you; to handle your self-loathing as a serious mental-health issue that merits careful, attentive, loving treatment; and to consider what kind of life you might like to build for yourself outside of (or, let us say, in addition to) romantic considerations.

By Daniel M. Lavery. HarperCollins.

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Dear Prudence,

My boyfriend and I just celebrated our third anniversary. We bought a home recently after nearly two years of living in an apartment, and want to get married someday. I have one child from a previous relationship, who adores him, and he treats him as his own. He's been great in his fatherly role. I have been upfront with my boyfriend about certain things I will not tolerate (dishonesty and cheating are the big deal-breakers. My child's father cheated on me, and I eventually left him). Our relationship is strong, and we are happy. I found out recently that just before our first anniversary, he went to an ex-girlfriend's house after he spent some time at a bar that he goes to occasionally. This was previous to our living together, but we were exclusive. I assume he was there either late, or spent the night. I don't have details on that. I just know that he bought beer and went to her apartment. I can only assume something happened, especially since he never mentioned going to a friend's house afterward (he usually does). I’m crushed. I never knew this information before, and had I known at the time, we would not be where we are today. I am heartbroken, disappointed, and feel less confident. It wasn't like we were together for a few weeks—it was almost a year. I feel he not only hurt me, but by extension, he did a disservice to my child as well. They are not friends on social media. Since two years have passed, should I say anything? Do I keep this secret to myself? What can I do?

If you have the opportunity to trade vagueness for clarity, back channels for direct conversation, and uncertainty for honest self-disclosure, I can't imagine why you wouldn't say something to your boyfriend. Based on your letter, it sounds like you found out this information from a possibly misinformed third party; who better than your boyfriend to fill in the details of what actually happened? You trust him, he's given you no cause to doubt his word, and your relationship is otherwise good, so speak up. Don't lob accusations or fill in the blanks for yourself, but tell him that you’ve recently learned something that makes you uncertain and anxious, and you’d like him to tell you what happened that night. Then listen. It may be he admits to something you find unacceptable; it may be that he has a perfectly legitimate explanation; it may be that you two have to fight about this, or break up, or laugh off a misunderstanding. But give him the chance to shed light on what is now just a rumor.

As an aside: I understand the desire to overstate hurt in the absence of information, but whatever happened that night was not an act of disrespect to your son. This is about you and your boyfriend, and it's unnecessary to insert your son as a proxy into a conversation about your feelings.

Dear Prudence,

My wife and I have been married many, many years, with all the ups and downs that long-term married couples are familiar with. She will soon go to a sunny resort with her girlfriends and is looking forward to relaxing and having fun.

I would like to suggest to her that if the opportunity arises to have an erotic encounter she shouldn't feel guilty. At the same time, I don't want her to feel like I am pushing her away or that I expect reciprocation. We still have the hots for each other. Should I even raise the subject, and if so how do it tactfully and lovingly?

It's fine to broach the possibility, but right before she leaves on vacation with a group of her friends probably isn't the best time. "Have fun with the girls! I’d like to raise the subject of an open marriage, call me when you land!" You can bring it up with her, but "just before she boards a plane" is not a great time. If you want to talk about it, talk about it, don't just tell her what you want without giving her the chance to consider or reject the idea.

It's a bit disingenuous to phrase your interest in this as a generous offer—"I could take it or leave it, the idea of you sleeping with someone else, I just thought I’d let you know that it would be fine with me, in case you’ve secretly been cherishing the thought but felt guilty about it. Because I would hate for you to feel guilty for even a moment. Not that I’m interested in the idea. I am not. This is purely borne out of my deep consideration for your hypothetical feelings." You have to acknowledge the fact that this interests you; you can't try to mitigate a possible rejection by pretending you think this is what she wants, but has been feeling too ashamed to bring it up with you.

I’m sure you can find a way to bring this up lovingly, but I’m less sure about how to make it tactful. This is not a tactful subject! It's a bold request, and one that she might very well reject. There are a few ways you can try to make sure you frame it as kindly as possible, although there's no guarantee that she won't say no. Make it clear that you’re happy with your sex life the way it is (it sounds like you are), and this is purely a sexual bonus round, rather than something you need in order to stay happily married but have been keeping from her for years. Tell her it interests you, but if it doesn't interest her, you won't push her on it. Then genuinely don't push her on it if she says no.

If you bring it up, you run the risk of her being angry and hurt at the very idea. If you don't bring it up, you run the risk of never finding out she's into it, too. It's up to you to figure out whether or not this is worth the risk. Either way, you’re lucky enough to have been married for a long time to someone you’re still in love with and attracted to. Congratulations!

Dear Prudence,

I work in IT support for a large corporation. Last week I got a call for assistance in fixing an executive's email account. During the course of the incident, I read some of the emails. It turns out that she uses her work email for personal business as much as for work; there was one long conversation with a friend about how she was attracted to a woman working in the mailroom. This caught my eye because the younger woman is my sister. She was unable to get a job for a long time after college, and I got her the job about a year ago. While grateful to have a job, she's understandably frustrated with the menial nature of it. Also, while in her senior year she came out to me and close friends, but has never had a girlfriend—something that also depresses her—but she's shy and doesn't know how to go about dating. I want to tell my lovely, talented sister what I know about the executive's interest. I think that it could be helpful for her to know that someone successful is interested in her, and if something came of it, it couldn't hurt her career prospects either. What do you think?

I can think of about 47 different ways this could go horribly wrong. Say nothing. What on Earth could your sister do with this information? "Hey, I read one of our executive's emails, and she thinks about you, like, all the time. So, the next time you hand her her mail … make a move." Just because this woman wrote to a friend about her workplace crush doesn't necessarily mean she's available or interested in a relationship with your sister. There's also no guarantee that this executive's romantic interest would actually help your sister's career. Nothing good comes of reading other people's emails. Let your sister work on her romantic shyness and career prospects on her own, and try to forget what you read.

—Danny M. Lavery