How to Do It is Slate’s sex advice column. Send your questions to firstname.lastname@example.org. Don’t worry, we won’t use names.
Every Friday, Stoya and Rich will answer one more question in chat form. This week, a no-sex sex question.
Dear How to Do It,
I am an almost 30-year-old straight woman who’s never had sex. No P-in-V, no oral, not even heavy petting. I have kissed two guys, neither of which were great experiences. (My first kiss was five years ago, and he went from zero to tongue-down-throat.) Because of some life messiness, I also haven’t dated much. All of this is to say, I am super inexperienced in all aspects of relationships. Now that I’m in a more stable life place, I’m trying to get into dating, but my inexperience keeps tripping me up. I’m not even comfortable making out with a guy on the second date, but on the past few dates I’ve been on, these guys have gone for it and I’ve just frozen up. I get way too in my own head wondering if I’m awful at kissing, and does everyone hook up on the second date, and oh God now I have to tell him about how I’m a virgin and he’ll judge me? On the second date, I don’t even know if I want to have sex with the guy yet. It generally takes me a while to build up attraction to someone. So he thinks I don’t like him or I’m frigid, and I figure it’s not fair to string him along and break it off.
A lot of advice I see is to just be upfront about who you are and what you’re looking for, but whenever I go out with someone from a dating app, no one wants to move more slowly. So I’m not sure if I need to suck it up and do things that make me uncomfortable, or if I need to disclose my lack of history upfront and hope they don’t think I’m crazy or laugh at me. What should I do?
Rich: This one is really hard.
Stoya: I don’t even know where to start.
Rich: Obviously, we can’t and won’t diagnose sexuality, but I wonder how much time she has spent thinking about whether or not she is asexual. It really seems like the very prospect of any sort of physical intimacy is daunting to her.
Stoya: I’m not so sure because of the part about potential partners thinking she’s frigid, which implies she does have desires. But I might be reading the sentence wrong now that I’m looking at it a second time. She also mentions “life messiness” as a barrier.
Rich: Yeah, it’s hard for me to tease out how much she genuinely wants to experience sex from how much she thinks she should want to experience it, which leads to a lot of anxiety as she measures herself against what she thinks she should be. I think it’s telling that she hasn’t had sex yet because maybe, in fact, she doesn’t want it at all. Cool! There’s no right way of doing life, and sex isn’t mandatory.
Stoya: I did some reading up on asexuality for a different question recently, and there are people who identify as asexual who also date, snuggle, and possibly kiss.
Rich: It’s amazing how sexuality never stops spectrum-ing.
Stoya: It really is.
Rich: Between each shade is an infinite number of shades.
Stoya: I want to directly address the part about sucking it up and doing things that make her uncomfortable. Don’t do that. Stick to your boundaries.
Rich: Totally. Doing something that will make you uncomfortable will likely only make you feel worse. And for what? A sustained situation (i.e., a relationship) of discomfort. I understand that she feels like she might have to bend to join the status quo, but she’s better off taking this at her own pace.
Stoya: I think she might want to be upfront about her sexual history to save herself the time of dinner with someone who might reject her because of it.
Rich: And time, after all, is the most precious resource we have. It’s the one thing we’re all running out of. As painful as it might be, it’s worth preserving.
Stoya: The more I think about it, the more your asexual guess seems like it might fit.
Rich: Just a hunch! I don’t want to say that and thwart her exploration. But I do want to underline that it’s OK if that’s what she is. Regarding the fear of being judged: Sharing time with someone, even briefly, means you’re running the risk of them judging or laughing at you. This is true of all social situations, but especially intimate ones. I don’t think there’s any way around vulnerability, other than closing yourself off and denying yourself your desires. Ultimately, neither guarantees comfort, but you miss every shot you don’t take.
Stoya: So there is one uncomfortable thing to suck it up and do: Be vulnerable. Which is really the hardest sometimes.
Rich: Especially with virtual strangers!
Stoya: I’m wondering if she has friends she can practice talking about this with.
Rich: Yeah, this is definitely something that I think would probably get easier to talk about with practice? Right now it’s like a taboo wrapped in taboo. There’s a certain amount of seal-breaking that needs to be done. I’ve found that a lot of sexual anxiety erodes with experience. Of course, sometimes that anxiety inhibits experience, but if you want to get anywhere, your resolve has to be more vicious than the cycle.
And while it’s true that you don’t come across a lot of 30-year-old virgins, I think a lot of guys wouldn’t mind that at all? I personally love a project and wouldn’t be turned off by showing a dude in his 30s the ropes. It sounds hot.
Stoya: Yeah, I can absolutely imagine some men being nervous and others overeager, but also think it’s totally possible to find someone nice and experienced who wants to show you around. So many people develop new parts of their sexuality in their 30s.
Rich: I sure did! I think there is some fear on her part that, by revealing her particularities upfront, she’s limiting her dating pool. But she is a special case whose pool needn’t be infinite for her own sake. So that limitation is a good thing. Yeah, it might take some time to find the right guy, but if she’s going out with these dudes who want to stick their tongues down her throat on sight, she’s wasting her time on the wrong guys anyway.
Stoya: I don’t actually know how dating apps work.
Stoya: But maybe that’s the place to be upfront. I assume there’s some place to mention things like, “I want to take things slow. Really slow. Like kissing after a few dates slow.”
Rich: Yeah, most if not all have such space in their profile templates.
Stoya: It might be worth being that direct that early.
Rich: Directness is the only method that has ever worked for me. Granted, I have no choice but to be direct (terrible liar, all thumbs when I attempt to beat around the bush), so directness is the only method that I’ve ever employed. But still: It’s effective! It’s like that Madonna quote: “A lot of people are afraid to say what they want. That’s why they don’t get what they want.”
As far as the other anxiety she has (“I get way too in my own head wondering if I’m awful at kissing, and does everyone hook up on the second date”), I think like anything there’s just a process of growing into yourself. You’re not awful at kissing if you’re enjoying it.
Stoya: Avoid chewing on the chin unless requested, keep your tongue out of their nose, and you’re probably fine.
Rich: I definitely do a lot with my tongue, and some guys like it and some guys tell me, “Too much,” and really, whatever! OK! Maybe I can modify in a way that I still find true to my expression, maybe we just shouldn’t be kissing then?
Stoya: Right! It might seem counterintuitive since your mouth is kind of busy, but you can totally provide verbal feedback during kissing. So if something is too intense or doesn’t feel good, you can say that. And that applies to every step of exploring.
Rich: Exactly. And there are dating apps, by the way, that cater to specific types like sapiosexuals or asexuals. So there are those routes, too. I think mostly what this situation could use is a change in attitude/perspective—yes all of this is scary, but it’s also exciting. It’s a journey toward pleasure or at least knowing yourself better than ever. Oh, the places you’ll go! Oh, the people you may or may not make out with!