The Enduring Appeal of a Skater Boi

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Photo: Daniel Grill/Getty Images

My friend Olivia is someone I thought I knew and understood. She is a 30-year-old professional with a solid career and a tastefully appointed apartment. She pays her taxes and eats well. But I recently learned that Olivia has an unusual thirst. I do not mean the thirst of dehydration in our increasingly inhospitable landscapes under the reign of global warming; I mean a more unquenchable desire.

The mysterious yearning of which I speak, of course, is skater lust.

Indeed, longing for skater boys has swept through parts of our nation at a formidable pace. It is a craving that is not easily extinguished nor easily cured. It seems that when skaters are not grinding and sliding on their decks, they are grinding and sliding with their dicks. And though dreamy-eyed teen girls would presumably be most vulnerable to the wiles of these foxes on four wheels, it is perhaps adult women who have found themselves most besotted with the enchanting ragamuffins ollieing their way into our grown-ass hearts.

I was first made aware of the skater-as-adult-lust-object when Olivia found herself romantically and sexually entangled with not one but two skaters. I was skeptical of the second dalliance because the skater in question was quite a bit younger. But when she shared photos of an angelic 22-year-old with golden-blond hair hanging just past his shoulders and an enviably even tan, I could not deny it: He was a stone fox.

“I want you to know that I think you’re a megababe,” he had whispered to Olivia after the first time they had sex. On that same night, he and his friends were kicked out of a hotel room for being too rowdy and resolved not to find a new hotel but to sleep in truck beds in the parking lot like a regular gang of vagabonds. Skaters live by their own laws, you see.

I learned that skater lust was more than the anomalous predilection of a rogue pervert friend when my friend Rachel told the tale of picking up a young skate enthusiast at 4:30 a.m. She found him on the street, where he and his one true love, a skateboard, were plying their trade on four wheels as dawn approached. Rachel is 30 but is frequently mistaken for a teen, so it was no surprise when she reported primarily attracting art-school girls and skater boys from the Lower East Side lately. “I started feeling like it was my duty to take them home, like I was giving back to the community,” she told me via text. More than once as she left her job at a club in midtown, she has heard the skater mating call of “Hey, baby girl” and it has culminated in her taking one of these ruffians home.

"Picking them up is very easy,” she explained, when I asked how she lured these skaters to her bedchamber. “But then when you get them back to your place ... it's like, what have I done!? Sometimes the dick is great but a lot of times they are too scared to perform at all and they just wanna listen to the Weeknd." The cruel paradox of the skater is that the same low-pressure attitude that makes him so sexy is the same attitude that may make him opt out of having you sit on his face in favor of vibing out to "Can't Feel My Face." Live by the sword, die by the sword, I suppose. 

But because the laws of God and man mean nothing to the skater, some abuse their prowess with petty-crime sprees. “I’m always paranoid they’re going to steal from me because THEY DO. A skater boy stole $700 from my room,” Rachel reported. I was horrified; she was not: “What’s $700 for a little skater love?”

Search “skater boys” on Twitter and a flood of horny, infatuated tweets will cascade down your screen like a perfectly executed drop-in on a sweet ramp. They range from tender longing (“Skater boys will forever have my heart”) to unbridled desire (“I love y'all disgusting ass skater boys come kiss me on the face fuck me up”). Still more express mixed feelings (“I love skater boys but they're so vicious”) and pondered what engagement with a skater boy might to do them (Poll: Skater boys will ... 56% Break ur fuckn heart 44% shred your pussy hair). Frankly, I’m not sure which of these poll options is more appealing.

But why? And what, for grown women, was the appeal of banging these kick-flipping lotharios engaged in a pastime so inextricably linked to middle-school youths?

“The appeal is an accident. I AM THEIR RELUCTANT QUEEN,” Olivia exclaimed. But this was perhaps not the whole truth. She had her reasons. She noted that their athletic bods were often banged up in a perfect Goldilocks ratio of smooth, sun-kissed skin to skating scars. “The appeal began just because they're so sexually nonaggressive, which is rare and refreshing in men,” she explained more seriously. “They have a specific confidence and I'm not sure where it comes from (since skateboarding past childhood is objectively embarrassing) and they for the most part really care about skateboarding as a lifestyle, which I find endearing.” This theme came up often: the appeal of the skater’s un-self-conscious interest in the sport that brought new and literal meaning to the idea of freewheeling.

Lindsay is 32 and has the distinct honor of being common-law married to a 34-year-old skateboarder. She too finds the enthusiasm attractive. “When he starts nerding out about skateboarding, I honestly get wet. I could listen to him ramble on about skateboarding for hours. Not because I really love listening to very technical and specific details about certain skaters or styles or tricks, but because his enthusiasm is contagious and endearing,” Lindsay told me in an email. In a culture that champions being blasé as integral to a certain kind of hipster masculinity, being stoked about skateboarding is charming.

The element of nostalgia also played a crucial role — women described middle- and high-school days spent pining over skater boys. Lindsay recalled trying to watch them skate in the back parking lot known as a congregating spot for “bad” kids. “There was this sense of danger about them,” she said. “Growing up in a very strict household, I was immediately drawn to anything that seemed rebellious.” I must admit experiencing a similar attraction when I was in middle school. My own community in northern San Diego was plastered with stickers that read “Skateboarding is not a crime” in response to the petty laws prohibiting the sport in schools, parking lots, and other public spaces. In a not especially exciting or dangerous suburb, skating seemed downright dissident before we were old enough to be politicized.

And while I hate to spoil an otherwise tongue-in-cheek story about fucking dudes on skateboards, there was something almost melancholy about the desire of the women I spoke to. There was a thread of longing for our own youths, which we either miss or wanted to do differently. “Dirty skater boys were who I should have been dating when I was fifteen,” Rachel recalled. “But instead I was on internet forums talking about what we would do when we were adults.” Rachel grew up in Kentucky and had fantasies about Manhattan that centered on Harmony Korine–like figures, and credits her present attractions to those visions. I too ended up with a lot of unrequited love for the scores of skater boys whose singular focus on their sports made fascinated girls like me less than a blip on their radar. Crushing on the men such boys became is an extension of that youthful longing.

Olivia mentioned her own Peter Pan Syndrome in our conversation, noting that none of the skaters she’s encountered are judgmental about it the way other men have been. Peter Pan Syndrome, or puer aeternus, is the condition of being perpetually in the mind-set of a child or teen and is considered more common among men than women. “There is a terrific fear of being pinned down, of entering space and time completely, and of being the singular human being that one is. There is always the fear of being caught in a situation from which it may be impossible to slip out again,” writes Jungian analyst Marie-Louise von Franz in The Problem of the Puer Aeternus.

Of course, an interest in skateboarding or the people who skate is not a measure of maturity. But social expectations are more forgiving of men than women choosing to extend an adolescent mind-set into adulthood. The attitude of skaters — at least those who match the nonjudgmental, earnest, enthusiastic, and independent archetype — can be a welcome reprieve from double standards around female behavior, at least for those of us with a lingering attachment to the freedom of youth. “At the same time, there is a highly symbolic fascination for dangerous sports (particularly flying and mountaineering) so as to get as high as possible,” continues von Franz in the description of the puer aeternus. “The symbolism being to get away from reality, from the earth, from ordinary life.”