How to Do It is Slate’s sex advice column. Send your questions for Stoya and Rich to firstname.lastname@example.org.
Dear How to Do It,
I am a single woman in her early 30s. I’m attractive and have never had issues attracting a partner. But after a series of disappointing relationships, each around a year, I’m just not in a mood to engage emotionally with men right now. The thing is, I have a high sex drive, and I can’t fully satisfy myself on my own—though believe me, I try. The cliché is that this should be an easy problem to fix: Plenty of men want to have sex with a woman with no strings, right? Here are my limitations: In the past, when I’ve had hookup buddies, I like them, but it never really is just sex—we inevitably get to know each other better and then I end up getting entangled with him, whether I want to or not. I also am not really into sex parties or the poly scene; for better or worse, I like the intimacy of one-on-one connections, even if all I want is sex right now.
So I’m not really sure how to proceed. I’ve identified a few bars in my town that are … good for this sort of thing, but that is hit or miss for finding an attractive guy. When I tell my gay friends about this, they talk about how easy it is to find what they want on Grindr and the like, and I’m honestly jealous. Tinder and similar apps for straight people are full of creeps who have no game, and I’m afraid if I’m upfront about what I want, I’ll attract even more of that type. What’s a straight girl who just wants good, unattached sex to do?
—Tinder’s No Grindr
Dear Tinder’s No Grindr,
It’s true—even when both parties are completely uninterested in anything serious or romantic, you can still eventually end up in the bath-products aisle together debating whether your connection means anything and having moments of odd, sticky feelings toward each other. In your case, it sounds like at least some of the entanglement is coming from your end. So put reminders in your phone: Make the guys have names like “Chris Nothing Serious Johnson” or “Joe This Is Just Sex Beatty.” Whatever will underscore the boundaries you’ve set and need to respect for yourself, in addition to expecting the guy to adhere to. Hopefully that’ll make it easier to keep a good casual connection going (once you’ve found an acceptable partner) without tipping into what you don’t want.
As far as apps go, I’m wondering if you’ve specifically tried Bumble. I have participated in precisely zero dating apps, so I can’t say how the quality of interactions compares exactly, but having women as the initiators as a feature might help you cut down on the noise from people you don’t find appealing from a cursory profile scan. I’m also wondering if it’s possible to go back to former flings for another round or two. Having a few partners you see somewhat less frequently might make it easier to prevent the entanglements that can result from too much close proximity.
Still, unfortunately, you’re going to have to get out there and wade through at least some potential creeps. They might all turn out to be mostly benign, but some might not. They’re a part of single and sexually active life. Meet in public places that are likely to have people around, be careful with the location of your home, and remember you can always leave if you get uncomfortable or feel a weird vibe.
Dear How to Do It,
I’m 40, in decent shape, and have my life together. I’ve had two longish relationships, 10 months and three months. I was a late virgin—I lost it at 35 to my then-girlfriend through internet dating. I’ve dated more than 40 women (from 2014 to 2016) and took three to bed total. I’ve been told my penis is “above average” size. Gotten compliments on how great my butt is. I’ve also been told I’m an “incredible” kisser. I’m funny, smart, and an award-winning screenwriter.
But … the biggest negative is that I’m short. I’m 5-foot-5. I’m also not white. I’m Indian. In online dating, height is a major thing. After two years of no dates and no responses to literally thousands of likes and swipes and messages, I have no confidence left. I’ve made new profiles with new professional pictures. Female friends have helped me make my profiles. They’ve been sweet and tried to help me by saying nice things to me and being kind to me. But I’ve not had a date in more than two years. I’m really worried that it’s my height.
Recently, I met a woman at yoga. She’s the most beautiful woman I’ve ever met. I’ve had two good conversations with her. I’m not sure if she was giving me a vibe or any signals. She was very breathy when we talked and appreciated me “sharing my practice” with her. But I’m not good at reading flirting signals, so who knows? I know that if she gave me a shot, I’d be a good catch. But I haven’t seen her at yoga for almost a month, and I’m not sure what to say, if anything, if I do. What should I do?
—Tall Enough to Ride
Dear Tall Enough to Ride,
Dude. You say you have a penis, and the general vibe you’re giving me is heterosexual man, so I’m hoping it’s OK to call you dude. So: Dude. I’m so sorry you’re outside the standard search settings height-wise. (And yes, as you imply, nonwhite guys can face racism on dating apps as well.) In the grand game of dating, you have in fact been given a difficult hand to play.
Let’s start with the woman you already know from yoga. If you see this woman (and I hope you do) again, be direct and gentle. Start with something like “I was hoping I’d see you again.” Look her in the eye and speak at a medium pace. Enunciate well. All of this helps you put your best self forward. She could have been breathy from the walk over, or the class itself, but she also very well could be into you. Don’t fixate on her—brace yourself for everything from exuberance to rejection—but those kinds of interactions could be a better path forward for you.
In the event you don’t see this woman again soon, I do think getting out into the world and arranging to be in places with other live humans where you can show off your sense of humor and personality is the way to go. Take some random classes, go see some shows, or pick up a new hobby. Maybe even consider giving a new yoga place or two a try. You seem like you have a rational grasp on your dating prospects, especially in the online and app world, despite a slightly later start and barriers that aren’t your fault. I hope you can find the confidence to put yourself out there in creative ways until you find a solid match. You sound like you deserve it.
Dear How to Do It,
I am a person with a vagina, but I have never enjoyed vaginal penetration. But I do enjoy anal sex. How do I broach this with a potential sex partner without it being weird?
—To the Back
Dear To the Back,
“I prefer anal sex. As a recipient.”
Really, it’s that simple. Focus on the positive you want to highlight or the action you want done—as opposed to saying “I don’t like vaginal penetration”—and ask for what you want.
OK, OK, it’s possible that a potential sex partner might take that weirdly, or get weird in some other way, or just be weirded out. “It being weird” is a very real risk you take when you practice partnered sexual behavior. In fact, a weird reaction from a potential partner can be useful—with your tastes, how much time would you want to spend getting to know someone who thinks a preference for anal is odd?
Dear How to Do It,
I am a 28-year-old woman and have been in an exclusive relationship for seven years. I had several partners prior to my long-term boyfriend. But I have never had an orgasm. I’ve always had a relatively low sex drive, rarely masturbate, and don’t watch porn. I do enjoy sex when I’m having it; I just don’t seem to experience the intensity and release that other women describe. My partner is generous in bed and is among the top two partners I’ve ever had. He enjoys going down on me, and yet, nothing—in fact, I prefer penetration over clitoral stimulation.
After discussing my “issue,” a friend bought me a small vibrator for my birthday last year and told me to practice. After 10 to 15 minutes of use, the intensity gets too much and I “ejaculate” a small amount of fluid in a way that feels like I’m peeing my pants. But it doesn’t come with any feeling of relief or pleasure that others describe. I’ve been advised to keep going but afterward, I’m too sensitive for that. Can you come without orgasming? Am I having the most disappointing orgasms of all time, or not having them at all? What can I do to make one happen? Should I focus on penetrative stimulation instead?
For what it’s worth, a partner once told me that I had “the smallest clit” he’d ever seen. I am frustrated, embarrassed, and disappointed. Please help me!
— Come-pletely Frustrated
Dear Come-pletely Frustrated,
Before we dig into your actual issue, we should address the partner who told you that you had the smallest clit he’s ever seen. Clitoris size is like penis size—wild variation occurs, and some people fetishize the big ones. Big clitorises might be easier to find and keep hold of during stimulation, but there’s no evidence that a certain girth or length is required for orgasm.
I asked a professional to weigh in on your other specific questions. Deb Yeager, a certified sex therapist in New Jersey, told me you should consider psychological factors. You may be overly expectant of “fireworks” because of comparisons with adult films and steamy romance novels, or what your friends have told you. She also notes that “for some, it happens, and is not recognized”—in other words, not all orgasms are earth-shattering. Yeager recommends that you do some introspection, specifically looking for potential shame that could interfere with relaxation and your ability to let go, and to think about what sex is and means to you, including formative experiences. She also suggests you try masturbation and sexual interactions at different times of the month, since hormonal changes can have a noticeable effect on sexual response.
If you still aren’t experiencing pleasure from ejaculation or clitoral stimulation, I say stick with penetration for a while. Consider an insertable toy or two. I understand why you are frustrated, but I don’t think you should be embarrassed. It’s good you’re enjoying sex when you do have it. Do mention this to your gynecologist next time you’re in their chair, and good luck as you continue to explore.