How to Do It

I Married the Only Woman I’ve Ever Slept With

Now I want to know what I missed out on.

GIF: Woman kisses cheek of man clearly thinking about something else while neon question marks glow 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 was a virgin until age 23. I guess if I were in this position these days I would be classified as an “incel,” although I’m glad that godawful term didn’t exist back then. The main reason I was a virgin that long was because of wild levels of anxiety/panic I’d experience whenever I contemplated rejection, along with a way-too-idealized vision of what I wanted in a romantic partner that contrasted with my actual sexual desires. I was also obsessed with my best friend’s girlfriend (no bueno). In other words, it was much easier for me to masturbate about people I desired than confront my fears.

So at age 23 I had sex with the person who became my girlfriend … then my wife … and now we have a toddler! We have a decent relationship and a sex life that is mostly vanilla with some sparks of domination/submission on both sides, a little bit of butt play, trips to the sex toy shop, etc. Although our sex life these days is severely constrained by stress and busyness, we have a method for both of us getting off before the toddler wakes up. But as with a lot of people in my position, I feel like I missed out on some sexual exploration since I’ve only had one sexual partner. I’m curious about what sex with other people is like. I don’t want another romantic relationship, but my wife would definitely not be open to the possibility of me exploring NSA sex with sex workers or acquaintances. I’m willing to be monogamous for her, but it does lead to a certain level of frustration/regret. So, what am I missing out on? What am I not missing out on? I’d like to hear from the perspective of people who have had a variety of sexual partners/experiences.

—One and Done

Dear One and Done,

The term incel has been around since at least the ’90s, and reportedly had a very different culture around it than the frequently misogynist and sometimes violent group we see today. I wouldn’t say that includes all 23-year-old male virgins, for the record.

To address your actual questions, I’ve had sex with a number of people. A large number. I still wonder what new people would be like in bed. I still experience surprise, and delight, and find new ways of interacting. I’m still learning things about my own body. I’m still exposed to new sensations.

I’m guessing you would also still wonder about people you meet, and still be surprised by new kinds of touch, even if you had many partners before you met your wife. You might be missing an experience with someone’s specific kink, the rush of flirtation, crushes, and new relationship energy. You’re definitely missing constant stress about sexually transmittable infections, the exhaustion of stilted, awkward first dates, and the work of establishing—and keeping track of—individual boundaries and preferences. You’re missing waking up in strangers’ apartments and trying to track down your panties or manties in the near dark as you curse your habit of flinging them dramatically as you disrobe. You’re missing dating sites, drinks in bars that are too loud, and dating apps, too.

You’ve got a decent relationship with the mother of your child and a sex life with plenty of variety. If you’re feeling like you’re missing out on something specific (foot fetish? raccoon cosplay?), you can and probably should bring it up with your wife. Speaking of bringing things up with your wife, you say your wife wouldn’t be open to the possibility of NSA or professional sex experiences, but you don’t say that you’ve asked. It’s worth directly addressing your desires before resigning yourself to a binary choice. And it’s worth taking stock of all the great things you do have in your relationship with your wife and focusing on those positives—many people date for years in the hopes of finding what you have.

Dear How to Do It,

My question is about getting comfortable masturbating when it’s emotionally really difficult. Cis woman, bi, late 20s here, with a trauma history involving domestic abuse and sexual assault, as well as several years of health and career issues that have made it hard to find time and energy to date and have sex. It’s been over five years since I’ve done it with someone else (which I think was the right choice for my personal growth and priorities), but I’d like to have sex again at some point. It’s pretty scary though.

I’ve got a whole pile of issues around sex and relationships that I’m working through with a therapist. (None of it has to do with seeing sex as dirty or shameful; it’s more that I’ve had bad experiences, and I associate sex with consent violations and unhealthy relationships.) I’ve realized it would be good for me to masturbate more as a way to get back into a place of comfort and psychological safety with my body and sexuality. But unlike how I felt in my teens and early 20s—I was basically masturbating daily when I wasn’t hooking up with someone—for the last couple years, I only feel in the mood a few days out of the month. And when I do masturbate, it’s really emotionally fraught. I’ve always needed 20+ minutes to come. At this point, I’m just as likely to start crying before I get there and feel even worse than when I started. I think this is creating a vicious cycle where I put too much pressure on myself to “perform,” and it makes it hard to relax and enjoy things. I think I could also enjoy masturbation more often if I made time for it, but I worry that setting a designated time will just lead to more pressure on myself. Once my life is a little less of a mess, I want to try dating. But for now, how do I approach self-love in a way that doesn’t feel more stressful than loving?

—Beating Around the Bush

Dear Beating Around the Bush

You’ve had this realization that masturbation might help you get past your trauma, but have you talked about this with your therapist? I’m not a psychologist, and I really think you ought to address this specifically with your therapist. What you’re describing sounds alarming—like you might be getting triggered and experiencing flooding. Flooding can make your situation worse, possibly leading to you re-experience trauma, and how to navigate that is both out of the scope of this column and my expertise. Please talk all of this over with your qualified professional who knows your unique case. You have an expert who is wholly focused on you at regular intervals. Use that resource.

One thing you can do in the interim is start gathering data. When you do feel like you’re in a mood to masturbate, are there any common factors—perhaps a smell caused arousal, or some thought drifted through your mind? And if you do try to masturbate, are there any differences between the times you cry and the times you don’t? Are there common thoughts or memories when you cry? Or is the whole thing mysterious and unfathomable to you? Whatever information you do have or can discover, write it down. Bring that info to your head doctor.

And during the actual act of masturbation, consider how you’re treating yourself. Are you on a quest to achieve orgasm? If so, you might be putting too much pressure on yourself. It might help to reframe the activity from “barreling toward the big O” to “gently stroking myself, and if an orgasm happens, that’s fine.” Best of luck getting this part of your life back as you’re ready.

Dear How to Do It,

I’m a happily married straight man in my 30s. My wife and I have been together for 20 years, and we love each other very much. Our only problem, as I see it, is our different levels of comfort and desire with sex. She’s a once-a-week person, while I’d prefer at least three times. I’m happy to try new things where she prefers predictability. I find her more attractive each day; she thinks this part or that part of her is gross. I’m open and eager to having sex-related discussions to better our sex life; she shuts down when it comes to this, as though an adult discussion using grown-up sex words is something to be ashamed of. You get the idea. The most progress toward middle ground we’ve made in 20 years has been having sex less frequently and repetitively, her being more vocal during sex (moans, but never words unfortunately), the welcome use of a vibrator, and watching porn together when the opportunity arises (though she’s “not been in the mood” for this for nearly a year, making me question her enjoyment of it at all and curious if she’s just been appeasing me all this time). Don’t get me wrong, I’m grateful for these changes, but I know we can do better.

I’ve taken every effort I can think of to help her express whatever desires and fantasies might be in her brain that she’s too scared or ashamed to let out. They’ve been ideas that allow her to take part without vocalizing them—we write them on pieces of paper for the other to read at their leisure, both of us filling out a sexy questionnaire I created and comparing answers—but it was clear she would do them because I asked, not because she wanted to. I’ve been trying to do things myself so she might be comfortable following my lead: saying what I like during sex, telling her how hot she is, being VERY open about my likes and what fantasies/desires I have, sending her steamy but not vulgar sexts. Again, nothing.

I’m sure this isn’t uncommon. Millions of couples undoubtedly deal with this. But I’m completely at a loss as to how to proceed. All of this makes me feel undesired by her. I feel untrusted, saddened, and angered that after 20 years, she’s not comfortable enough to share this kind of stuff with me or even have an adult conversation about it. And I’m frustrated with what feels like being the only one that prioritizes our sex life and seeks to improve it. I welcome any input you might have.

—I Want It All

Dear I Want It All,

My hackles went up as I was reading your letter and I can’t put my finger on why, but I think you need to do some serious introspection into your behavior. Have you really listened to your wife? Have you been pushy? Have you been coercive?

It concerns me that your wife’s increased aural feedback, vibrator use, and participation in watching porn aren’t enough of a compromise for you. You don’t sound very grateful to me. I’m alarmed that you can express concern that your wife may have been appeasing you this whole time and then, in the next paragraph, express anger that your wife hasn’t become as comfortable as you would like her to be. The two of you might have unfortunately mismatched libidos, but you married this woman, and when you did that you took her as she was, not as your fantasy of what she might be if she were just a little more something.

I could be way off base here—lack of context can make for misunderstandings—but I have a hunch that you’re overly focused on your own desires and expecting more than is really fair from a woman with a lower drive and more reserved sexuality than your own. I hope you take a hard look at what you’re asking of your wife.

Dear How to Do It,

I was married for over two decades to a man I was with most of my adult life. He could be emotionally abusive, and from early on, our sex life was dominated by his insecurities about my previous lovers. I was, for the most part, fairly shut down sexually with him. When we were intimate, it mostly ended up being about him and was unpleasant if it wasn’t. I knew, especially during the last several years, that I was really missing out on a lot but had been convinced that it was mostly my fault. (Yes, I am seeing a therapist.) The biggest sorrow of those last few years was heading into my 40s thinking that my chances of having a passionate, loving sexual relationship with someone were wasting away as I got older.

I did leave my husband, and I did find someone not long afterward with whom I have had an amazing sexual relationship. At first, even men my age seemed to have watched too many Hollywood movies and thought women should climax within five minutes of penetrative sex (which I do not), but this new man was very attentive to me, and after a while I did start to communicate more. The problem is the relationship is probably ending. I am experiencing an incredible amount of grief over the loss of the sexual relationship because I know that it takes some time to find the right person to really develop the comfort and trust with that person. I definitely feel as if I have a lot more to discover about myself sexually, but I need the time and proper context to be able to.

I didn’t realize how much emotion around sex I had been suppressing until the possibility of losing this relationship became a reality. Like crying every day about it. Hardcore grief.
I live in abject terror that menopause is looming in my future, and once I have turned that corner, my sex drive and sexual enjoyment will drop precipitously. It feels like a ticking bomb. I have gone online and met some nice men, but it’s an odd context for meeting people and I really am not interested in just sleeping with random men off of the internet in the hopes I find one I click with. I feel like I just discovered really lovely sex in my late 40s and now I may never have it again because, by the time I find the right person, it will be too late.

—Too Little Too Late

Dear Too Little Too Late,

I’m sorry you spent two decades in that relationship, and I’m happy you’re moving on, seeing a therapist, and working on yourself. Now I’m going to scold you.

Way too much expectation seems to be the theme of the week. Yours is of the borrowing trouble variety. You sound like you’re starring in a movie, frantically racing the clock to find the right cock before the bell tolls 51. Your clitoris is not Cinderella’s carriage: It isn’t going to turn into a pumpkin at midnight. Actual elderly people still have sex. I know because I can look up the STI prevalence reports. Pre-menopausal is a long way from elderly. You’ve got more time than you seem to think.

You left your ex-husband and found someone not long afterward. These are your own words. Why do you think it’s going to take so long to find another someone? You don’t have to sleep with random men to find out if you like them. Do it the other way around—find out if you like the man, and then sleep with them and find out if you like doing that together. You still absolutely want to take the time to develop trust, but the more you practice open communication around sex, the better you’ll get at it. You will become more comfortable with—and efficient at—asking for what you want and explaining exactly how you like it.

You’re not even sure this relationship you’re currently in is ending, and you’re already mourning the loss of it. Some reframing might help, in case it does end—this person came into your life to show you what you’re looking for. To set a higher standard and raise your sexual aspirations. To lay bare the possibilities of sex and inspire you to seek new worlds of dick, or vagina, or whatever strikes your fancy.

Get out there and reject a bunch of men until you find one you want to fornicate with. You can do this. There is no deadline. There’s hope for your libido and life left in your lady parts. Go! Live! Enjoy!

—Stoya

More How to Do It

Dear How to Do It: My boyfriend is, uh, huge. Long and thick as my wrist. We go slow and use lots of lube, but we’re currently in that new-relationship period where we just want to screw nonstop as often as possible. How do I avoid the constant soreness, which I often don’t even notice until after?