Longboarding My Way Out of Loneliness

When I tried to skateboard as a kid, the neighborhood boys refused to welcome me. Now, women and gender-diverse people are creating skateboarding communities all over the world.

I am nearly thirty, but still on occasion find myself succumbing to (or delighting in) the risk-taking nature of my youth. I have passed the quarter-century milestone where one’s frontal lobe becomes fully matured and welcome any small return to that sensation-seeking, impulsive state of being that sets aside fear to invite new experience—as long as I can maintain my learned ability to calculate consequence. Something misfired one afternoon when I convinced myself I could do a barefoot ollie on a longboard without watching a single instructional video.

My first attempt at skateboarding was in the early 2000s, when Avril Lavigne’s Sk8er Boi was rocking out over every popular radio station. I was ten. I pored over the Let Go album cover with the washed out background and Avril’s pouty pose, envying her loose tie tossed over her shoulder, her eyes thick with black eyeliner. Now, I better understand my childhood connection to Avril: She had an unabashed confidence in her gender and the way she expressed it. I memorized the lyrics from the album booklet and sang to my stereo, inserting myself into the story of the song. Sometimes I was the girl at the studio with the Sk8er Boi, other times I was the Sk8er Boi himself.

I bought my first skateboard for $24.99. I’d been eyeing it for weeks. Each time I passed the toy section at a department store in Oahu, I slowed my pace to double check that the board hadn’t disappeared from the shelf. Once I saved up a small sum of cash from washing my parents’ car on the weekends, I brought the new board home, peeled away the stiff plastic that encased wheels the color of milk, and ran my fingers along the scratchy black grip tape. I grinned. My transformation into Sk8er Boi was a kickflip away.

When I brought the board out to my driveway, the realization dawned that one does not just ride a skateboard, one must learn to ride a skateboard. My throat was thick with disappointment. I’d expected to land ollies the minute those fresh wheels smacked pavement; instead, I could barely ride back and forth. I pleaded with the neighbor boys to teach me, but they refused. I was confused. It seemed as though there was a rulebook to playing with the boys, one which became more enforceable as I aged: Only on their terms, only in specific games—otherwise, I was an interloper. I watched wistfully from afar as they practiced skating on scraps of wood nailed together into haphazard ramps.

Nearly twenty years later, the TV series Betty debuted on HBO, featuring a group of women skaters in New York City based off of a real life skateboard group called Skate Kitchen. Betty was released in the midst of the Covid-19 pandemic, and I, like many, turned to TV to bring a sense of normalcy among the chaos.

I savored each episode, goosebumps scattering across my skin with a delicate sense of possibility. Here were a group of young women who didn’t look down on beginner skaters, but encouraged them. They spent their days popping off sidewalk curbs and skatepark ramps, getting high on mushrooms in the park, and supporting each other through sexual assault and complicated family dynamics. My heart ached with longing. I glanced out the window, where sidewalk steppers repelled from each other as if they were identical poles of a magnet, terrified of the virus sweeping the globe. I resigned myself with the conviction that my dream would have to wait, just a little longer.

My transformation into Sk8er Boi was a kickflip away. 

*

I am an introvert and adhering to the “stay home” recommendation was, at first, a delight. But after some time, a foreign urge to socialize kicked in like a hunger pang, and the solitary pain of loneliness pinched my chest with anxiety.

To be lonely is to be in a state of physical and mental adversity. Loneliness is biological, a warning sign, our brain’s way of signaling that we must seek human connection, must seek it now. Loneliness increases the likelihood of earlier death by twenty-six percent. We are social mammals, even when we consider ourselves introverts, homebodies, people at peace among quiet.

Months into the pandemic, my drive to seek connection nagged at me with a primal intensity, not dissimilar to hunger pangs or sexual arousal. This desire to socialize had a voice. “Attend to me,” it said, “Attend to me now. Can I make it any more obvious?”

I nervously asked a friend if I could try out her spare longboard. I’d read longboards were simpler to learn on than skateboards, their chunky wheels and longer deck providing better balance. She agreed. The apprehension I felt was a reminder embedded into my psyche of those neighborhood boys who told me I wasn’t one of them, wasn’t part of their crew, when all I wanted to do was skate.

I brought cans of grapefruit sparkling water, which we sipped while we rolled along a residential road. As we coasted down mellow hills I was struck by how similar longboarding felt to surfing. It had been years since I’d surfed; I’d long left Oahu for Winnipeg, an ocean-less prairie city. I closed my eyes for a split second and the pavement became waves. The minute shifts of my hips turning the creaky wood beneath my feet were the exact same motions as on a surfboard.

To be lonely is to be in a state of physical and mental adversity.

I quickly discovered the connection I’d made between the two was the original point of the activity. Longboarding was invented around 1959, alongside the entrance of commercial skateboards. Surfers in Hawaii wanted something to do when the waves were too rough or too low. They wanted a way to move their bodies using the environment around them when their beloved waterborne activity was unfeasible. The sport was known then as “sidewalk surfing.”

Bolstered by my first successful practice session, I started scrolling through skateboard reviews, and after days of watery-eyed brand comparisons, I selected a board with images of brightly colored Bird Of Paradise plants, the same flowers that grew in my backyard in Oahu. I figured the purchase would encourage me to spend time outside the walls of my apartment, even if alone. I cracked open the cardboard box, placed the brand-new board on my carpet, jumped on it barefoot, and promptly broke my toe.

So much for my childhood dreams. I iced my purple toe in twenty-minute segments and considered that it would be easier, and far safer, to give up the activity once and for all. But as I stared at my knees, still bearing splotchy scars from childhood cycling injuries, I was reminded of the fact that though I currently do not fear falling off my bike—cars hitting me are a much greater concern—I feared this plenty as a child. It didn’t matter that I had quickly transitioned from learning how to ride to simply riding. The fear remained for years, until the scars stopped itching and the falls were long in the past. Practice doesn’t make perfect, but practice makes practice. There was no reason not to apply this same philosophy to longboarding. Giving up on longboarding at the first injury would be succumbing to the overwhelming, long-lasting power of learned fear.

I started spending evenings on a small patch of empty concrete, weaving the board in figure eights as the sunset painted the sky with soothing tones of pink and orange. This practice allowed me to reconnect to my body in ways I didn’t realize I needed: Learning to longboard requires an intense focus. Correcting imbalance necessitates seeing in, listening in, to the intricate motions of the body. The distraction of a car or another person can trip you up, literally and figuratively, reminding you of all the reasons you should not be doing this. It is an exercise in growing from failure, again, and again, and again. And it is easier to lift yourself back up from failure when you have a helping hand.

I wanted to be a part of a group like the Skate Kitchen. I wanted to bumble around with other beginners at the skatepark and study the balanced, adventurous experts. After enduring catcalls and condescending comments while skating around my neighborhood, I did not want these people to be men. (Sorry, boy, but you missed out.) My concerns are echoed by women and non-binary skaters around the world, who are carving out spaces to uplift each other in a sport dominated by men. Many use social media to post meet-ups, allowing tentative beginners to try their feet at this invigorating activity.

I sought out Winnipeg-based skaters on Instagram, and found three accounts: Queer Skate Winnipeg, Turtle Island Skaters, and Board Broads. The three were collaborating to host Sk8 Against H8, an anti-oppression skatepark event. Still too timid to venture to a skatepark alone, I enlisted my friend to join me. I slathered on sunscreen in preparation for a day outdoors in a heat wave. We tentatively stepped onto the smooth pavement.

Learning to longboard requires an intense focus.

“I don’t know why I’m so nervous,” she said, giving voice to my thoughts. It was a first for the both of us. But as we glanced around, I saw a true mix of people that filled me with the same sense of possibility I felt when first watching Betty, when listening to Sk8er Boi. Young girls were zipping around on penny boards, a toddler was giggling as they climbed stairs and ramps, and folks of various body types, racial identities, and genders were taking up space, even though many, if not most, were new to the sport.

I practiced doing wide turns on a low ramp. I took off my helmet for a moment, only to promptly fall and bonk my head. I was uninjured, but it scared me enough to put the helmet back on. When I finally achieved the turn without falling, adrenaline shot through my body. My persistence worked.

Later, we sat under the shade of an old elm tree while the event organizers shared their personal connections to skateboarding. Stories of experiencing misogyny from skater boys, claiming rightful space on stolen Indigenous land, and accessibility in skating sung to my sensibilities. Picking up a skateboard when you held an identity that was not welcomed in the sport was a political act. I felt seen.

*

The skateboarding world is changing from the one I first approached as a ten-year-old Sk8er Boi wannabe. Skateboarding is now an Olympic sport, with the first games to be held in 2021. Alexis Sablone, a pro skater and queer woman, will compete as part of the US Olympic team. Leo Baker, a trans non-binary person who has been skating pro since 2006, is a seven times X Games medallist. Still, cisgender men continue to outnumber women and non-binary people in pro skateboarding and are favored for sponsorship opportunities, making a livelihood difficult if not virtually impossible for women and gender-diverse pro skaters. For those of us amateurs, however, women and gender-diverse people are creating skateboarding communities all over the world where we can gather, from Skate Kitchen in New York City to the Board Broads in Winnipeg.

I felt seen. 

I have learned there is a secret language between skaters, a sense of knowing and understanding that by sharing in this activity, friendships can blossom, and simultaneously, one’s own skate skill set can improve. At Sk8 Against H8, I joined a group chat with sixty participants and growing. Sixty potential friends I can message when I want to visit a skatepark and don’t want to go alone. Sixty women and gender-diverse people who aim to make skateboarding inclusive and inviting for people of all levels.

The antidote to loneliness is connection. Each time I fight past my fear of the outdoors and don a mask to visit the skatepark with a new friend, I am inviting myself to listen deeply to my physiology, to the signals from my brain that urge my attention towards my most prominent needs. And even when I am practicing alone on that empty patch of concrete, I know I am never truly alone. Because I am surrounded in spirit by a community of women who are trying this out for the first time, too: falling, bruising, and picking themselves back up again. If you’re a fellow wobbly adult and you’re feeling even a smidgen of doubt about trying it out, know that there is space at the skatepark for you, too. You just might have to be the one to create it.