How to Do It

I Have a Secret—and I’m Terrified to Tell the Men I Date the Truth

A woman's silhouette with a line around her.
Photo illustration by Slate. Photos by Getty Images Plus.

How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!

Dear How to Do It,

I am a mid-30s straight-ish woman. I once dated a lot, but I have not had sex with anyone since 2019 because I am too self-conscious about my new reality: I started losing my hair a few years ago. Aggressively. I have seen many, many specialists and tried many, many treatments—nothing has been effective. This is just something I will have to learn to live with. As it has progressively thinned, I have used different hairstyles to hide my scalp. At this point, I have so little hair that all I wear is a slicked-back ponytail, or I am always in a hat. I feel my face is too masculine for me to be confident with a shaved head. I have tried wigs and think they look like a weird helmet on me, but I know I will need one eventually.

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I want to date again. I used to love sex and dating when I felt attractive and feminine, but I no longer recognize myself in the mirror. So much of my femininity was wrapped up in my hair that I feel less like a woman now and more like an “it.” So much so that I feel surprised and confused when men show interest in me. I avoid them because I know they’re interested in women, and I am afraid of being “discovered” as a fraud. I am seeing a sex therapist about my identity issue and improving my self-esteem. I am working hard to develop the confidence to date again through books and journaling.

I started seeing one man recently after getting vaccinated. For two months, we went out on fun dates, talked a lot, and really connected. Physically, we only made out a few times. I was at his house one day and he casually asked me why I never wear my hair down. It took a lot of guts, but I told him. He was really nice about it—said he didn’t care, would shave his head right then—and asked to see. I said no, we moved on, and the rest of the day was fine. Then he was weird to communicate with for the next couple days. Finally, he called and ended things for a supposedly different reason that he had never brought up before. It is very hard for me to not link the rejection with my revelation. I was devastated.

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I love physical intimacy and fantasize all the time. All that is holding me back is my attitude toward my hair. My question for you is—how do I let partners know about my secret? I know my ponytail will fall out during the kind of sex I enjoy, and I know I will instantly feel like Gollum. I don’t see how I could be free and playful and enjoy myself when all I think about is my hair, hiding it, and what my partner thinks (my assumptions jump to the worst things I think about myself). To avoid that, I know I need to discuss this with a partner ahead of time. The only way to enjoy sex again will be if I don’t have to worry about surprising them and instead know that it is not an issue for them. When do I tell future potential partners as to A) not wait too long that I’m emotionally invested in someone who I am not compatible with (I am aware and OK with the reality that most straight men will not be attracted to this situation), and B) not be too quick that I have to be vulnerable and reveal this to men before I know what kind of person they are (for fear of them reacting very negatively). Is there any way I can present this information in a way that will make the rejection hurt less if it is something they’re not into? And then for eventually when/if I start wearing wigs, how do you have sex with a wig on?

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—Bored and Bald

Dear BB,

Cam performer and ostomate Go Ask Alex did an explainer video a few months ago (adults only, paywall) on disclosing disability for the magazine I co-founded. The gist of what she argued is that the way you raise your difference with a new partner frequently affects how the other person responds. In other words, the more casual and matter-of-fact you can be, the more likely it is that the person you’re seeing will be chill or treat this like a nonissue. That said, negative reactions do happen, and they can be difficult to predict. You can spend some time now thinking through how you can best extricate yourself in the event a reaction becomes too stressful.

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When to disclose anything is a balance, like you describe. I’d caution you against spending too much energy trying to prevent negative reactions—they’re a real possibility, and someone can be very accepting of most things yet still harshly judgmental of a few. I think the main factor is your comfort: You say it took a lot of guts for you to explain why you never wear your hair down, and that’s relevant. How much time spent getting to know someone do you need before you feel comfortable sharing this aspect of yourself that you’re sensitive about? That’s likely to shift as you practice discussing your hair, and also to vary depending on the specific person. (You can do that practice in the mirror or with your therapist as well to help yourself feel more natural when the time comes.) You say you know that you’re going to have to accept your hair loss, and that will mean accepting that sexual partners will know about it, too.

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As for having sex with wigs on, you can set yourself up for success by going for a shorter style so there’s less chance of the ends getting stuck under a body part and the wig getting ripped off. You can also use wig tape to prevent slipping around. Solid construction helps, too. With wigs, you do get what you pay for, and you might achieve a less helmet-y look with the help of a hair stylist—many are happy to cut and style your wig for you.

Take it slow. There’s no rush. But do keep working on this, because you make it very clear you don’t want to forgo the physical intimacy you love.

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Dear How to Do It,

My wife and I have been together for 10 years. I need some help with how to ask for the things I want in the bedroom. I want to better own my wants and needs. There is no orgasm gap in our sex life. I make it a point to listen, learn, ask, and explore what my wife wants and needs. I love touching, teasing, tasting, and being a part of her orgasms. She has a voracious sexual appetite—in terms of receiving. And that’s totally awesome. I just feel like I’m left in the dust when she’s exhausted.

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I can’t remember her ever asking “does this feel good to you” or “what can I do to make you feel good.” There isn’t a curiosity from her toward me. When pleasure is focused on me, it is “have to” sex not “want to” sex. There isn’t much enthusiasm for my pleasure. I’ve begun to realize that her lack of enthusiasm for me is a mirror of my lack of enthusiasm for myself. I want to speak up for what I want. I want to feel WANTED by her. As it is now, it feels like she only wants just enough so that I orgasm, and it’s over. Our usual sexual script is a long focus on her with lots of orgasms and then a quick finish for me. I’ve succumbed to this, and I want to try to change this without upsetting her.

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—Speaking Up

Dear Speaking Up,

You’re clearly missing something in your sex life, and it seems to be attention. Spend some time thinking through what you’d like. Is it a massage? Thirty minutes of nonorgasmic stimulation on you? Oral sex performed on you? All of the above? It’ll be useful to be able to ask for something specific and provide examples of what you’d like to experience.

Pick your time. Do you have time to talk significantly, and deal with any potential fallout from the conversation? Is everyone alert, well hydrated, and properly fed? Have you minimized the potential for interruptions? And are you in a space where you can comfortably look at each other as you speak?

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Start with your dedication to your wife, and the joy you take in the sex the two of you do have. Then explain something like what you’ve said here—that your pleasure doesn’t feel necessary or celebrated, and that that’s an uncomfortable feeling. Give her the space and opportunity to respond and ask you questions. Draw on the years of life and mutual respect the two of you share, and start thinking about solutions together.

Dear How to Do It,

Greetings! I’ve had multiple sclerosis for 40 years, and in 1987, I stopped having orgasms. Imagine my surprise and delight when for some untold reason, about three years ago, I suddenly started not only having orgasms but desiring sex! It was wonderful! My husband is 76 and on antidepressants, and he has difficulty maintaining an erection. My husband has spoken to his doctor, who suggested that he not take his antidepressant the morning of the day he is planning on sex, but so far, that hasn’t worked for us. Is there some sort of toy that we could use to enhance our experience? We would prefer that this toy still provide him with some sensation, and I would prefer that it enable him to stay erect inside me, or feel as if he were. He has admirable circumference, but he does deflate.

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We are certainly enjoying foreplay and lots and lots of oral sex, which blissfully is what we both prefer, but we both do love P-in-V, except that he kind of MELTS.  We’ve tried a cock ring, which was OK, but when we tried a sleeve, we had no idea how to fit the thing, and the one we got was far too small, even though it was labeled extra large. How do we approach this? Do we call customer service? Help, and THANKS!

—Insatiable After All These Years

Dear Insatiable,

I’m thrilled for you!

The short answer is yes, you call customer service.

Every toy is different, and every penis is different, and it’ll be a lot easier for you to call the customer service department of the manufacturer of penis sleeves that y’all are interested in than it will be for me to try to find a vaguely “wide” sleeve. Ask for measurements.

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I also encourage you to follow up with the doctor who prescribes your husband’s antidepressants. His initial suggestion didn’t work, but he might have further ideas. You don’t mention if E.D. drugs might be a possibility, for example. Good luck.

Dear How to Do It,

I’m a woman in my 20s and have identified as bi for a few years, after having debated whether I was straight or gay for many years before that. I used to be completely unable to describe “my fantasies,” and that was not even part of how I masturbated (I basically would just masturbate without really thinking anything that turned me on), but I’ve recently been getting in touch with fantasizing. It’s been great! What’s confusing me is that when I’m fantasizing, I’m always imagining encounters with a partner who has a penis. They’re often not men, but I can’t seem to bring myself to fantasize about a partner with a vulva. Same goes for sex dreams. Why is it so hard for me to stay in those fantasies and get turned on by them? Could it reflect an actual preference?

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—Dick Dreams

Dear Dreams,

Fantasies are funny. I’ve read countless perspectives over the years from feminists who have aggressive and violent fantasies, and countless responding takes saying that fantasies in no way indicate a desire for practical experience, or an approval, of sexual assault. I knew a guy who fantasized about having sex in a giant bowl of buttered pasta, and when I offered to make that happen in the bathtub, he passed. Try to think of fantasies as waking, lustful dreams—they don’t need to mean anything, they don’t need to dictate your actions, and they don’t need to make sense.

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I don’t know why your fantasies and sex dreams are devoid of vulvas, and I don’t know whether that reflects any sexual preference on your part. But let’s say it does. Let’s say your subconscious is telling us that you have a preference for dick regardless of the gender of the person it’s attached to. That would put you firmly in the middle of bisexual, which is your current identity, and therefore change nothing.

Have you had sex of any kind with other people? If so, your responses there seem more weighty when we’re thinking through the subject of sexual preference. If not, the same applies—get out there, and gain some lived experience.

More How to Do It

My husband and I have been together two years. About a year ago, I had sex with my best friend in front of him. That, uh, didn’t work out so well.

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