I’m Tired of Being An Older Virgin. What Should I Do?

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I'm Tired of Being An Older Virgin. What Should I Do?

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Estimated reading time: 13 minutes

Hey Doc. I’m in my late 20s, “pushing 30” as they say. I’ve never been in a relationship or had sex. I’ve suffered from anxiety, low self-esteem and depression much of my life, though I am taking medication and going to therapy. My dating life can best be described as a series of disappointments. All my attempts to ask women out in person (admittedly few in number) have ended in rejection, and my online dating history has hit a wall in the past year. I was having some success with online dating, but nothing that went beyond three dates. I haven’t been on a date in about a year now, partly due to the fact that I’ve been coping with the death of a close loved one, which basically shut me down entirely for a few months.

I think I have a high sex drive. I masturbate almost daily, sometimes multiple times a day. But Doc, all I’ve got is porn and Instagram models, you know? I’ve never so much as touched a titty or had an intense make-out session. I’m so far behind when it comes to sex and dating. So many people I know are getting married, and I still haven’t even had a single relationship yet.

I had always hoped I could lose my virginity to someone more experienced than I am who would help guide me through it, you know? But it feels like the older I get (again, pushing 30 here), it’s less endearing being a man with such little experience, and more like a glaring red flag.

I would like to gain more sexual experience. I’d like to play the field and have lots of casual sex. But first of all, I’m not hot enough to pursue casual sex (I’ve struggled with my weight my whole life, a huge factor in my poor self-image and lack of self-esteem and confidence with regard to dating, and I’m technically obese according to BMI). I know there are women out there who like bigger men, but that seems like kind of a niche subset of woman. It seems most women want either a guy with abs or a skinny Timothy Chalamet type they can baby. I’m SOL in that regard. I’m hitting the gym, but it’s going to take months, if not longer to begin to be in the kind of shape I want/need to be in to search for hookups. Second, I’m of South Asian descent. I don’t want to harp on this too much, but I know we’re not exactly the most popular ethnic group in the west, and I’ve read the statistics on response rates in online dating. Generally, I’m under the impression that most women simply aren’t interested due to my ethnicity. Add in my weight, and I’m already at two strikes while at the bat.

I can’t stand the dating apps anymore, so I want to avoid that avenue. But I just can’t see myself going to bars or clubs trying to convince someone to hook up. But I NEED sex, Doc. I’m going insane just jacking off. I’ve been seriously considering hiring an escort or flying out to Reno just to get the deed done. Maybe it’ll help “clear my head” and put me in a better state of mind to pursue sexual intimacy once I’ve actually done it. Just some intense petting and making out would probably do it for me at this point, doesn’t even have to be full-on-sex. What should I do, Doc? Should I pay for it to get it out of the way, or are there other venues I should try that aren’t online dating or bars? I feel like I’m running out of time, and that’s what scares me most of all. With every day that passes, I get closer and closer to being a 40 year-old virgin, and right now that seems the most likely outcome.

Unicorn Bait

Alright, I’m going to do something that I don’t do very often, UB: I’m going to give a bit of behind-the-scenes access here. This isn’t personal, so much as you just happened to be the lucky thousandth or so letter on the topic.

I picked your letter specifically because at this point I’m getting more than a little tired of getting questions about virginity that are so cookie-cutter and following the same tropes and complaints that it’s hard not to notice they follow a formula and they’re more or less all stemming from the same place. So rather than talk about what you should do, I’m going to talk about what these questions are actually about.

Spoiler alert: it’s not about sex. It’s about being validated.

9 times out of 10, literally, they bring up the same worries, the same complaints and more often than not, weird “nobody will ever touch a virgin because if someone else didn’t that means that there’s something wrong with them”.

Bonus points if they try to justify it by complaining about how it makes women think they’re a terrorist because of incels like Minassian, Rogers, etc.

This is frequently paired with complaints about how women only want certain body types or guys who look a certain way, frustrations with online dating and of course, the difficulties of navigating the bar and club scene.

The thing is, virginity is a money-soluble problem for men; sex workers exist, after all, and is legal in many places. As you say in your letter, UB: a trip to Nevada is relatively cheap (airlines have regular sales) and most of the legal brothels will even send a car to pick you up at the airport. It neatly solves all the problems someone might encounter if what they’re looking for is to lose their v-card status – you take away any question of whether or not sex will happen, you know exactly who you are going to sleep with, that they’ll be attractive to you,  and more often than not, it’ll be a positive experience because your partner will be focused entirely on your pleasure. As a bonus, most escorts are going to understand the issues most likely to come up (loss of erection, premature ejaculation, good old-fashioned stage fright…) because they’ve seen it before and handle it with grace and compassion. Many even offer what’s known as a Girlfriend Experience (that is: a session that feels more like time with a partner rather than a commercial transaction) or focused around first-timers.

But this is almost never the route the virginity-afflicted choose… not because of money or inconvenience – you’re likely paying more over time for roses on Hinge or Tinder Gold subscriptions and getting less for it – but because of what it means. Specifically: that they didn’t lose their virginity in “an authentic way”. Amusingly, this isn’t that far from the discourse around weight-loss drugs like Ozempic, when people tut tut over not losing weight “properly”; if the concern is truly about whether or not someone’s a virgin, why would it make a difference if their first time were with an escort rather than, say, a semi-drunken fumble with someone who was looking for the least objectionable warm body after closing time at the bar?

This is, to my mind, the single greatest example of how virginity is a social construct. If meeting the commonly held definitions of penetrative sex – tab a into slot b, repeat – can be disqualified because someone paid for it, then the issue isn’t virginity.  

The real issue is the desire to be chosen. To have their inherent desirability validated by the fact that someone chose to have sex with them, instead of with someone else. It hinges, in no small part, on the idea that women are the “gatekeepers” of sex and thus the ones who bestow validity on someone by fucking them.

It’s not really a surprise, then, how often these letters follow the same tropes and complaints. After all, they’re frequently coming from the same place – literally and metaphorically. They’re coming from people who have absorbed toxic ideas about what it means to be a man, mistaken ideas about women that, likewise, come from other men rather than from women and then buttressed by giving credence the worst or most reactionary takes that social media algorithms can throw at them without ever stopping to consider that maybe the subreddits or Discord servers they’re frequenting aren’t a reasonable or even representative slice of humanity. Especially when it doesn’t take much to go outside, look around and see how many imperfectly-shaped people are having sex, having relationships and otherwise living their lives despite not looking like INSERT_MALE_CELEBRITY_HERE.

This gets all the funnier as folks decry that women only want whichever celebrity they’ve zeroed in on, while women are out there talking about the horrible things they’d let Matt Berry or Jesse Plemons (or other folks who don’t look like they were carved out of marble and abs) do to them.

You’re not going insane from a lack of sex, UB. You may be horny, sure… but the issue isn’t going to be solved by a sloppy make out or a blowjob in a dive bar toilet. It’s not going to “clear your head” and make you feel less anxious, because the issue isn’t “haven’t had an assisted orgasm”. The issue is how you feel about yourself and the fact that you’re looking for someone else to validate you and tell you that you’re worthy.

But as I’m always saying: women aren’t Mjolnir. Women don’t just sleep with “the worthy” – and honestly, you just have to look at the relationship problems women write in about. They have sex for a voluminous litany of reasons, just like men do. Nor are women the “gatekeepers” of anything. While women are often the passive partner when it comes to initiating approaches with an eye towards relationships or hook-ups (for sociological and safety reasons, not lack of desire or a wish to see men dance to their tune), who approaches and who is approached doesn’t decide who the “gatekeeper” is. The approach is just the start of the conversation. The decision about whether they want to have sex is double-opt-in; the only difference is that men don’t think of the times they’ve opted out as counting because they’re more focused on the ones they’ve chosen.

Any woman, however, who’s had an unrequited crush on a guy or a guy who completely missed (or ignored or rebuffed) their attempts at signaling interest can tell you: guys are just as much the gatekeepers of sex as women are.

Your problem, UB, isn’t that you’re looking for loving in all the wrong places. There aren’t going to be magic venues that will eradicate the problems you’re facing, because the issue isn’t where you’re looking, it’s how you feel about yourself and the presumptions you’ve made about women. Your age isn’t the handicap you think it is, because it’s not the age that makes an “older” virgin less and less appealing, it’s their own attitude and beliefs about themselves.

Considering that you don’t consider yourself to be a catch, it’s going to be a lot harder to find women who will respond positively. Not because you’re right and there’s something unappealing about you, but because if you don’t think you’re good enough to sleep with, why would someone else think that? Nobody buys a brand of chips because they marketed it with “we kinda suck but maybe you’ll like us?”

This gets paired with the fact that your biggest handicap with dating involves the women you’ve made up in your own head to reject you. Your letter is littered with suppositions and guesses – “it seems”, “I feel like”, “I’m under the impression that…”. The only person who’s decided that you’re “two strikes before you’ve even gotten up to bat” is you. You and you alone are the person who’s decided that this has already happened and so now you’re barely willing to give things an honest try to the best of your ability. You’re half-assing your attempt to get ass; it’s hardly surprising that it’s not working out.

It also doesn’t really help that you’re hoping for two, relatively incompatible things. The odds that you’re going to find someone who’ll ‘show you the ropes’ but then won’t be an impediment to your then taking your newfound knowledge and going out to just carve a swath through the bars and clubs are low. You’re much more likely to find someone who’s going to be interested in teaching you what to do in the context of a relationship. Sex, as a general rule, tends to be better with someone you actually know and have a continuing connection to; you’re learning more about what they like and what you like and what works for both of you. A relative stranger isn’t as likely to have the same investment in guiding you through things – especially if it’s going to be a one-and-done. While you do occasionally find someone who’s willing to be an an angel investor in the startup that is your sex life, they’re few, far between and not likely to be doing so with someone who mostly views themselves with a mix of contempt and self-pity.

You have a similar issue when it comes to finding casual encounters. The math that women do to decide who they might or might not want to have a quick fling with is less about objective hotness and more “is the sex going to be worth the potential risks. Considering the orgasm gap that exists in most hetero pairings and the fact that a lot of guys who are looking for casual sex have a “got mine, screw you” attitude and don’t bother bringing their A-game, a lot of women are going to nope out without some serious signs that this is worth it for them. A guy who walks around with the attitude that he’s been pre-rejected before he’s ever said anything is not going to be conveying that Studly Good Night energy. That’s not about bedroom experience or hotness, it’s entirely about attitude and social skills. A virgin with a willingness to listen without ego and a can-do attitude is going to be more desirable than a dude with numbers that would make Wilt Chamberlin blush but who thinks that foreplay is something that happens to other people.

Now, that doesn’t mean that there can’t be challenges, don’t get me wrong. Asian men have long dealt with racist beliefs and portrayals of them as emasculated or less manly. Fatphobia is very much a thing. But as frustrating as those legitimate challenges can be, by accepting them as reasons why you’ve got two strikes against you is tacitly accepting that the other people are right, rather than seeing the folks who buy into it as wrongheaded (if aggravating) fools who are missing out on the best sex they’ll never have. If you’re going to start from a position of “they don’t like me and I have to work my way up to ‘neutral’” then you’re never going to have the confidence or sense of security necessary to actually get laid – certainly not to have sex that’s in any way fulfilling and enjoyable.

While you don’t have to think that you’re the hottest thing since World War III, you do need to believe in your own value, your own desirability and that being with you would be a good thing. If you don’t believe in yourself first, nobody else is going to be that invested in changing your mind – certainly not people you don’t already know. And as many folks who read this column can tell you: having to reassure someone that yes, you do bang like a screen door in a hurricane over and over again is incredibly tiresome and a libido killer.

So if you’re not going to go throw money at the problem via a guided experience with a sex worker, then your best option isn’t going to be dating apps or bars and clubs. It’s going to be working on yourself. Not getting Marvel Chris fit, but learning to not just love the shit out of yourself, but to connect with people on a social, intellectual and emotional way. Develop your self-esteem and your social skills. Learn how to make people – not women, people – laugh, feel good and otherwise enjoy themselves in your presence. Focus on connecting with folks and also how to express not just confidence but desire with confidence. Don Draper – human trash fire than he is – is charismatic in part because he doesn’t feel ashamed of expressing interest in people.

Once you stop looking to others to prove that you’re worthy, you’ll find more people who’re going to want to see if they can lift your hammer.

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