My dating life was preposterously successful. I dated exactly one person. Then she married me. We’ve been together 25 years.
That’s one way of looking at it. There are less charitable interpretations. I managed to marry the one person I seriously dated by not dating until I was in my late 20s. My wife is the first person I had sex with.
You could say that I’m the perfect person to write about dating — I got everything right the first time. Or! Perhaps I’m the worst person to write about dating, since I was terrible at it and ran or stumbled away from most women who approached me, until my wife cornered me at a party. (More or less literally; she boxed me in by the refrigerator. I had no escape, bless her.)
I’m a vaunting success or an abject failure. That split looks unusual. But I don’t think it is. Cishet men are encouraged to see dating as a competition — with other cishet men and with themselves.
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This isn’t a conversation that’s featured in dating columns much, in large part because cishet men don’t have much of a public discussion about relationships. Imogen West-Knights in a much-shared Guardian article wondered(opens in a new tab) why there are few relationship and dating columns by straight men, speculating that they may see writing publicly about dating advice as “undignified.” West-Knights interviewed a straight male friend who said he “wouldn’t be interested in reading a column by some dude ‘cos I’d just think, well, that’s him I guess. I can’t imagine finding it useful or applying it to me in any way.”
I haven’t had a boyfriend for a decade. Here’s what I’ve learned.
This lightly veiled hostility is not a surprising reaction; men are supposed to figure out how to be men without a lot of touchy-feely advice from other men. Heterosexual confessional dating stories by women in popular culture generally leave space for solidarity; women can find common ground in the struggle with the dead weight of male patriarchal assholery. Male dating stories, in contrast…also tend to figure men as struggling with the dead weight of male patriarchal assholery. Except, they’re not united. And the goal isn’t to overcome patriarchy so much as to take your place inside it.
Patriarchy treats women as rewards rather than people.
Queer theorist Eve Kosofsky Sedgwick argued(opens in a new tab) that intense relationships between men are central to patriarchy and supersede relationships with women. Or as she puts it, “the bond that links the two [male] rivals is as intense and potent as the bond that links either of the rivals to the [female] beloved.” Men are supposed to take a role of authority and mastery in society, Sedgwick says, and that role is validated, or contested by other men. In patriarchy, she argues, women are used as “exchangeable, perhaps symbolic, property for the primary purpose of cementing the bonds of men with men.” In other words, patriarchy treats women as rewards rather than people.
You can see this dynamic in the non-fiction media that purports to provide something like dating advice for cishet men. At best, it’s just straightforwardly instrumental suggestions(opens in a new tab) for dating women — people who are supposed to have found true love, or at least genuine connections, offering to help other people match their success. At worst, it traffics in ugly misogynist stereotypes and recommends outright deception and violence. Alleged sex trafficker Andrew Tate became incredibly popular by encouraging men(opens in a new tab) to assault women for cheating on them. Tate and his ilk present themselves as empowered hypermasculine models by embracing extreme misogynist violence — and teaching others to do so as well.
How pop culture shapes our concept of masculinity
Fictional mainstream explorations of dating for men are generally less openly violent, but they still tend to present male dating as a competition between men, with women as exchangeable tokens of status. That’s been the case throughout my life. In 16 Candles, which came out when I was in high school, the cool jock infamously hands over his drunk girlfriend to the nerd in exchange for the heroine’s underwear. In 1999’s American Pie, a bunch of high school losers seek to sleep with women in order to cement their bonds and status with each other. Supposedly in the MeToo era we’re beyond that. But films like Top Gun: Maverick, still treat their female leads as secondary to the main issue of male self-actualization. Pete “Maverick” Mitchell (Tom Cruise) shows he’s a man by successfully shooting down lots of other men, and then the plot hands him the attractive romantic interest as part of his general victory. The fact that this isn’t really a romance genre movie is part of the point; most romance specifically directed at male audiences is embedded in films where the romance is part of generalized manly success, rather than the main attraction.
When someone (like me!) says, “I didn’t sleep with anyone until I was 27,” the reaction tends to be, “What is wrong with you!?”
That’s the case in the gold standard of male self-mythologizing, the James Bond franchise. Bond famously cycles through “Bond girls” at the rate of two or more a film (though lately the filmmakers have tried to be more enlightened by cutting it to one, even including one character, Léa Seydoux’s Dr. Madeleine Swann, across two films if you can imagine). He’s a hero to many straight men who envy him, desire him, imagine themselves as him, precisely because women in the franchise are often presented as mere distractions from the narrative, as conquests. Per Laura Mulvey’s article(opens in a new tab) on the male gaze, the main relationship in the films is between Bond and male audience members who envy him, imagine themselves as him, and take vicarious pleasure in his victories.
Or take your eyes off the screen and consider your response to my own brief narrative. When someone (like me!) says, “I didn’t sleep with anyone until I was 27,” the reaction tends to be, “What is wrong with you!?” I must be ugly; I must have poor social skills; I must not bathe; I must be a raging misogynist incel.
I wouldn’t make any great claims for my looks or social skills, but for what it’s worth, I had a fair number of suitors over the years. I had plenty of female friends, as well as male ones. I correctly didn’t blame women for my troubles, or think I was entitled to a dating life. I wasn’t lonely or isolated or resentful. I was just somewhat shy, bad at flirting (so bad at flirting), probably, in retrospect, neurodivergent, and also just unlucky.
Obviously having a series of unrequited crushes is not a lot of fun. But the thing that really made me miserable was the way I compared myself to other guys. Sometimes the comparison was to very specific other guys. I try not to remember a particularly excruciating car ride conversation with swim team peers in high school. Everyone went around the vehicle boasting about the exact extent of their sexual experiences. For my part, I kept repeating, with puppy-dog (maybe neurodivergent) eagerness, “I haven’t done anything!” while everyone kindly and uncomfortably ignored me.
Our perception of people who don’t date
Even if there weren’t particular guys telling me I was a failure, I got the message. If I wasn’t having sex, was I even a man? Was I even heterosexual? Dating wasn’t just dating; it was an endless test I was endlessly flunking.
Like the friend I finally told about my crush and she told me she had a boyfriend I had somehow not known about. Or the date I ruined because we were talking about philosophy of science (my first mistake) and I disputed her assertion that gravity was caused by the earth’s rotation. (“I don’t want to talk about this any more,” she said.) Or the woman who canceled a date with me unexpectedly and I was confused for decades till she finally told me she’d wanted to sleep around and assumed I wasn’t that kind of guy (I would totally have been that kind of guy!). I could go on. But I would rather not.
In any case. That was all at the time humiliating and horrifying. But the truth is that, while I of course felt rejected by the women who were turning me down, it wasn’t the women who I felt most judged by. Per Sedgwick, it was men — or the idea of what a man should be in my head.
Real men are supposed to date and have sex. So what kind of man are you if you’re doing neither?
Other guys, I was aware, were dating women. Sometimes they were dating the women I wanted to date — as in a particularly painful freshman year triangle with my (supportive, kind, all around lovely) roommate. I still remember lying there in my room, waiting for him to come home, even though I knew he wasn’t coming home, contemplating my own inadequacy and general pitifulness. Do that for enough years, and you start to feel like you’re misshapen and broken. Real men are supposed to date and have sex. So what kind of man are you if you’re doing neither?
The nature of masculinity is that no one is supposed to feel they measure up; everyone is an inadequate patriarch trying to prove themselves, like Elon Musk throwing a tantrum when Joe Biden got more engagement than he did on Twitter(opens in a new tab). Musk’s a billionaire and one of the richest people on earth. But he still feels that he doesn’t measure up to some other man because of a meaningless metric.
How can men help dismantle misogyny and violence? This book will tell you how.
Misogyny and romantic rejection
Or as another way this dynamic can turn toxic, consider the incel community(opens in a new tab). Incels — self-described involuntary celibates who blame women for not dating them — claim to share an identity because they’ve never had sex and never even kissed. They gather in online forums to complain that women won’t date them, and instead date other attractive guys who aren’t as nice or awesome as they are. Incels have been implicated in violent acts of mass murder, in which some members of the community attempt to enact a twisted vision of “revenge” on women and on other non-incel men.
There’s intense pressure in the incel community to be, or claim to be, a virgin. But even despite that pressure, 15-20 percent acknowledged in a poll(opens in a new tab) that they’d had sex and/or a relationship. What binds incels is not a particular (lack of) relationship with women. It’s a toxic relationship with other men and with themselves as men. Women are just a scapegoat on which to project their resentment that they haven’t attained the James Bond-esque success to which they believe that, as men, they are entitled.
Most straight, cis men aren’t as rabidly misogynist as incels, luckily. But I think most men in our culture do, at least sometimes, feel like dating reflects on their status as men in a competitive field of manning. If you read about someone else dating, as a guy, you’re either looking up to them as someone to identify with or looking down at them as a failure to repudiate, lest that failure be yours. That makes it hard to muster the sense of solidarity, shared misery, and shared excitement which is the basis for many women’s personal writing about dating.
Fighting violence against women, we need men to be part of the conversation
So was I a great success at dating or a great failure? The answer is both, and neither, and that maybe we shouldn’t so often default to that question or the idea of “success” in dating itself. My dating history is idiosyncratic and somewhat embarrassing. But everyone’s history is idiosyncratic, and most people experience some level of embarrassment while dating. It’s not a failure to stumble around a bit, and if you don’t stumble — well, that’s not necessarily success either. Intimacy isn’t a contest, and caring about people doesn’t have a scorecard. We’d all be better off if men saw dating more as something to talk about, and less as something to win.
