How to Do It

The 30-Year-Old Virgin

I’m finally dating. Should I tell women my secret?

A man pulls away from a kissing woman with a neon flashing V in the background.
Photo illustration by Slate. Photos by Getty Images Plus.

How to Do It is Slate’s sex advice column. Send your questions for Stoya and Rich to howtodoit@slate.com.

Dear How to Do It,

I am a 30-year-old male heterosexual virgin. This is my deepest secret—the handful of times I’ve told anyone, I got such unmerciful teasing that I immediately regretted it. I have OK social skills, but have had few close friends—I grew up closer to my parents than to my contemporaries. Now my friends are starting to marry and have kids, which makes me more fearful that I am going to die alone. I spent high school being intimidated by the world of sex and dating, I spent college feeling self-conscious about not having gotten any in high school, and since college, I’ve been depressed about having not gotten any in college. I hate the bar scene, and I keep hearing nightmarish stories about online dating. But I am starting to do the online thing, and have gone on a few dates. No magic yet, but I am trying to build up my confidence.

But I am terrified of how a woman would react if she found out about my secret. Wouldn’t she immediately dump me for a more experienced guy? And I don’t know anything about how to have sex or how to tell if a woman is ready for it. I’ve watched plenty of porn, but I know that’s not reality. What am I supposed to do? I’m terrified.

—Old Man and the V

Dear Old Man and the V,

I’ll be honest: A woman absolutely might dump you over your inexperience. Another woman might see an opportunity to vicariously relive the early days of sexual exploration. A third may be so focused on and into you as a person that she doesn’t care either way.

It may be helpful to think about the reaction you want. Do you want someone who is excited to show you the ropes? Do you want someone who isn’t going to make a big deal over it? Do you want someone who is also relatively inexperienced to explore with together? These questions will help you know what you’re looking for, and when you’ve found it.

One of the problems with porn as sex ed is that most of the communication happens before the camera rolls. We establish partners and the broad strokes of the scene (anal? comedic? rough?) during the booking process. Performers speak before the scene starts about specific dislikes—and frequently likes as well. There are layers of consent around professionally made adult media.

You’re supposed to talk. You’re supposed to say, “I’d like to kiss you,” and see how she responds. You’re supposed to ask if the thing you’re doing feels good, or if she’d like it faster, harder, or more intense in some other way. You’re supposed to pay attention to positive reinforcement, and to try to keep track of what they like for next time. You’re also supposed to communicate about your own tastes and desires. This doesn’t mean endless chatter every time you have sex will be necessary, but open communication is essential as you get started, and it can be fun too.

You might consider Allison Moon’s Girl Sex 101 as an introduction to the mechanics of sexually pleasing women. You aren’t exactly the intended audience, but it’s succinct, fun, and holistic. Good luck.

Dear How to Do It,

For most of my sex life, I never had this problem. But in the past couple years, things have shifted. After a bad UTI, my boyfriend (at the time) and I couldn’t have sex for a couple months, so we would dry hump a lot. I learned how to get off in quick, innovative ways while fully clothed. The problem is that now whenever I have sex with people, I get off VERY quickly, and I can’t control it. Too quickly for my own liking! I feel it zaps the hot anticipation of the orgasm, and then I feel the excitement in the moment is gone, and I’m over it and ready to go to bed. Also, I need a break from the thrusting as soon as I orgasm. It’s made me anxious, and I don’t know what to do about it. By myself, I can get off many times. With a partner, I get upset when I get off too quickly.

I’m wondering if this quick orgasm is a problem (akin to premature ejaculation) with tools for a fix, or whether it’s a gift that I just don’t know how to harness, accept, or communicate about yet. I’ve read articles about how “female premature ejaculation is real and awful,” but I’m wondering if these articles are a product of the culture shaped by men’s experiences and the idea that coming too quickly is bad. Can it actually be awesome for a woman? I suppose I’m struggling with knowing whether this is a physical problem or not. All I know is it’s distressing me, and I’m having less sex as a result. I’d like to not come as quickly.

—One and Done

Dear One and Done,

Orgasming quickly and copiously can indeed be awesome. However, you’re saying you want more of a solution than an acceptance or celebration, so let’s deal with that first.

One thing you can do is pause during sexual activity when you feel like you’re close to orgasming. This is also called edging. The idea is to build the stamina to ride the edge of orgasm until your partner is ready themselves or after they’ve orgasmed, so you aren’t having to choose between stopping when you’re finished and giving your partner an orgasm. You might disengage from penetration to give them oral sex for a while, or fully pause and kiss for a bit. You’ll likely develop more finesse as you practice this, and you may come to find it enjoyable for its own sake.

You might also consider using a very strong vibrator on high to desensitize the tip of your clitoris somewhat, or use some numbing lubricant. You’ll want to be careful with the latter as reduced sensitivity could cause you to miss pain or injury. If you try it, it isn’t the day to try fisting or get aggressively pounded.

Since you can get off many times by yourself, you may decide you want to go the acceptance route. You might question why you’re responding differently with partners than you do solo. You might decide to push yourself through a second orgasm to see if your energy picks up again or interest becomes repiqued.

I also suggest that you mention this to your gynecologist on your next visit, just in case there’s something they can do to help you and to soothe any medical worries.

Dear How to Do It,

I am a straight man in a marriage to a bi woman. We have been a couple for over 15 years, absolutely love and adore each other, and have each other’s full trust. About six years ago, after we had been married and had our first kid, we decided to open our relationship. Mostly this has taken the form of playing with friends, and it has been generally successful in letting us try things we were unable to before (we were both each other’s first and only sexual partner up to that point).

Recently because of stress, antidepressants, and general life changes, my wife has lost almost all of her sex drive. We have fallen back on our open relationship for me to find physical intimacy with others, and it has been OK. I have realized that I want to be polyamorous, and my wife has been very supportive, helping me find time to go on dates with friends. She is always happy for my successes and commiserates when things don’t work out. However, most of my extramarital relations have been with former college friends who live two to three hours away.

I want to meet someone closer to my home, but I don’t know how to do that without outing myself. My parents and siblings would blow up if they ever found out I am poly, and my siblings are often on dating sites. The new people I tend to meet are parents from my daughter’s school who are very conservative and religious in a way that is a huge turn off to me. I work in a different city than where I live, but I work in a small field and I teach college-age students who may also be on dating sites, and I am not super comfortable coming out to my co-workers or anyone in my professional life. I don’t know what to do to be able to find someone that I can have a meaningful poly relationship with without blowing up my family life, my daughter’s school life, or my professional life. Do you know anywhere I could turn to get this to work? Or do I need to make the decision to out myself as poly to people who will hate or judge me for it in order to meet this need?

—Peek-a-Boo

Dear Peek-a-Boo,

Based on what you describe, you’d be taking a major risk by dating in the town you live or work in, and a decreasing but still significant risk the farther you get from either. Weigh the pros and cons. Make an actual list. Spend time inhabiting worst-case scenarios to the best of your imaginative ability. You and your wife have to make this difficult choice together, and—since you have young children and your parents aren’t likely to understand—I won’t be surprised if you err on the side of caution. You can always see if there’s interest in making the between-visit relationships with your former college friends more robust.

Dear How to Do It,

I am a woman, early 30s, in a heterosexual relationship with “Alistair” for a decade. I am also overweight with an eating disorder that caused a textbook yo-yo effect. My body struggles were not affecting much of our sexuality, and we kept over the years a regular and mutually satisfying sex life. Last semester was intensely stressful, so my weight has been creeping back up. Alistair also had a major depressive episode, which led him to take an antidepressant. The drug is lowering his libido, and our sex life is dwindling. Alistair is terrified by the lack of sexual intimacy, and he obviously cannot stop taking his medication, so he is exploring everything else that may lower his libido. He found that I am too fat for him. I feel deeply hurt and ashamed to not be attractive enough. I am now fighting the urge to diet or binge, and I cannot bring myself to be fully naked in front of him. I can barely stand to be naked when I am alone. What can I do to improve our situation? He is in therapy, but I cannot go for the moment.

—Yo-Yo

Dear Yo-Yo,

Is this the first time that Alistair has been unkind about your body? If it is, I suggest you tell him that his words hurt you and that you feel shame and inadequacy. You’re the only person who can say if this is out of character for him. He might be having a side effect from the medication, or he might be so stressed out that he phrased himself poorly.

If it isn’t out of character, I’m curious why you want to stay. Hearing negative comments about your body isn’t going to help you feel better about it. And—humiliation kinks aside—most of us aren’t exactly turned on by that kind of talk. Is he incredibly supportive in other aspects of your life? Is he coasting by on goodwill from the first few years?

Either way, you need to prioritize yourself and your own health. If being naked in front of Alistair makes your body struggles more difficult, refuse to do it. Take time to heal—as much time as you need. I know you say he’s terrified of the lack of intimacy. He will need to confront that fear if he wants to continue to be with you. Just like you will need to confront your body image again if you want to return to being naked with people (not to mention yourself).

You are worth that kind of work. Even if Alistair declines. Even if the relationship doesn’t work out. You are worth work, and emotional investment, and care.

—Stoya

More How to Do It

When I had sex with my first boyfriend when I was 17, he came very quickly, within a minute. He was embarrassed. I told him it was normal and that he would last longer the next time. The thing is, he never really did. The other thing is, I started to really love this. Well, we broke up last summer. My problem is that I miss my two-pump chump. Some guys can really go a long time and seem proud of their “stamina,” but I get pretty tired after a few minutes. This sounds ridiculous, I know, but what can I do here? Put on Tinder “must come embarrassingly fast during sex”?