Sexplain It: I’m a Gay Virgin and Dating Is a Nightmare

I’m Zachary Zane, a sex writer, author, and ethical Boyslut (a fancy way of saying I sleep with a lot of people, and I’m very, very open about it). Over the years, I’ve had my fair share of sexual experiences, dating and sleeping with hundreds of people of all genders and orientations. In doing so, I’ve learned a thing or two about navigating issues in the bedroom (and many other places, TBH). I’m here to answer your most pressing sex questions with thorough, actionable advice that isn’t just “communicate with your partner” because you know that already. Ask me anything—literally, anything—and I will gladly Sexplain It.

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Dear Sexplain It,

I’m 27, going on 28, and I haven’t had sex yet. I came out at 22, got into a situationship that was four years long and broke up last year. We didn’t have anal sex, and I didn’t really receive any pleasure during the said sex ever. He cheated on me with someone else in my house, and since then, I have moved to a different city, focused on healing and putting myself out there. My dating pool is quite limited even though I live in a tier 1 city in India. A lot of people compliment me on my looks and say that I’m one of the hottest gays in the city, but I don’t really believe that. Some good guys wanted to meet me, but somehow, I managed to bore them away.

This hot guy with a 9-incher recently got tired of me just texting and keeping things real, and he ghosted me. Another guy in an open relationship messaged me, but when I asked to meet up, he declined, which is stupid because why would you hit me up without any intention to meet in person? Just to ask if I’ve had dinner and if I’m keeping okay? I don’t even know if I want to have sex with someone who’s in an open relationship.

I’m confused. I don’t even feel sexually attracted to people anymore (only romantically). It feels like everyone just wants sex, and if I told them I’m a virgin and I don’t have any experience, I’ll drive them away.

The 28-Year-Old Virgin

Dear 28-Year-Old Virgin,

There is SO much going on here, just layers of questions and problems underneath one another, so let’s go ahead and break each down one by one.

First, let’s tackle the self-esteem issues and dating fatigue (i.e., learned helplessness—the belief that one is powerless to change a situation, leading to inaction.). Why don’t you believe people when they say you’re one of the hottest gays in the city? Why do you think you’re “boring them away”? If people keep telling you you’re hot, you’re probably hot. As for the boring them away? What? Do you think your company is that lame? Come on, dude. Perhaps they’re interested in sex, and when you aren’t, they move on, but that’s not “boring them.” That has nothing to do with your personality or vivaciousness. It just means you wanted different things sexually and weren’t a match.

I don’t mean to sound cold or unsympathetic. I can see you’re frustrated—exhausted, even. Dating apps can indeed be a nightmare, especially for a gay man who isn’t looking for casual sex, as most gay apps are catered to hooking up and not actually dating. But I’m sensing a little bit of a pity party that’s, frankly, not going to be productive.

This leads me to the second major issue: The fact that all gay men (seemingly) want casual sex and are turned off by the fact that you’re a virgin. (Plus, the fact that you want to have an emotional connection with a partner before having sex with them.) First, I want to say I’m proud of you for not just “getting it over with.” I feel like many men would have in your situation. While I understand the desire to be done with it to lose your V card, I don’t believe you should have sex with someone unless you really want to have sex with them.

From the sounds of it, you are possibly demisexual, or somewhere on the asexual spectrum. I define demisexual in the glossary of my book, Boyslut: A Memoir and Manifesto, as “People who experience sexual attraction only after they have an emotional connection with someone. Demi people don’t see a ‘hot’ person and think, ‘I wanna sit on their face now.’ Only after having a heart-to-heart where they feel safe and emotionally connected do they sometimes desire the aforementioned face-sitting.” Conversely, you may be completely asexual and have no desire to have penetrative anal sex. Considering you were in a situationship with a man for four years, didn’t have anal sex once, and didn’t enjoy the other sexual stuff, sex might simply not be something you’re into.

Conversely, it could just be that you two had a crummy sexual connection, or you may be a side. The term, coined by sex therapist Joe Kort, Ph.D., is defined as a gay or bisexual man who doesn’t have a desire to partake in anal penetration (both receiving or giving) when having sex. Sides typically do all the other stuff, handjobs, ass eating, making out, and oral sex—just not penetrative anal.

While data is limited, anecdotally, side is an extremely common position—so much so that popular gay dating/hook-up apps like Grindr, Sniffies, and Archer have “side” as an option to pick when choosing your sexual position.

If you feel these terms resonate with you, I would list them on the apps—both demisexual and side. This will decrease the number of people who message/match with you, but that’s the whole point: filter out people you’re incompatible with. You only want to meet up with other demisexuals (or guys who are okay to take things slowly) and other men who don’t put such a focus on anal penetration.

They do exist—I promise you they do! But unless you are upfront about your intentions and desires, you’re going to keep running into the same issues (men who solely desire casual sex or don’t want to date a man who hasn’t had penetrative sex). So be upfront in your profiles and see if you can meet sexually like-minded men.