Why Washed-Up Dudes Like Me Can’t Let the Skateboard Go

There’s no better use of quarantine than embarrassing yourself in front of the kids at the skatepark when you eat shit trying to kickflip

I was returning home with my monthly haul of quarantine groceries a few weeks ago when I found a three-foot-by-one-foot package waiting for me on my doorstep. The tail of a skateboard was poking out of the corner, so I had a pretty reasonable guess about its contents. What I didn’t know was why someone would have sent me a skateboard. But I opened the box, and sure enough, there was a brand new board with a note from my cousin John. “Hey, cuz, we’re skating again,” it read.

Apparently, John had been using his quarantine time to reconnect with our favorite teenage pastime. He is a father of three now, trapped inside his Massachusetts home during the pandemic, and skating has been his only daily reprieve. He recently took a spill attempting to 180 over a sewer cap, and his wife now forces him to wear a helmet. (When I told him I was writing this story, he asked that I please not include that detail, but I’m sorry, it’s just too funny not to mention.) He also paved his entire backyard, which he claims was to give himself more room, but I think he just doesn’t want his neighbors seeing him eat shit.

I’d not thought about attempting to skate again in years. These days, I’m more prone to thinking about “getting my steps in.” I take lengthy walks in the afternoon, and incidentally, there’s a skatepark across the street from my house that I like to cruise past. I wouldn’t dare become one of those old guys I hated as a kid — the kind of grown man who thinks he’s impressing teens by telling them he used to skate “back in the day” and asks to use their board so he can show them the world’s shittiest kickflip. Such guys always wore huge basketball sneakers or dress shoes that wreak havoc on grip tape, which always made me think, If he was the former skater he claimed to be, he would know that. So instead, I just sit nearby and watch and listen to the noises the local kids’ skateboards make on the pavement (which, now that I think about it, is much creepier).

Many years past my skating prime, the sounds still trigger my sense memory. What I remember most is the noise my wheels made when they hit the concrete — a high-pitched squeal, a skateboard’s way of saying, “You fucked up.” My board would instantly stop dead but the force of momentum would carry my body another several feet until I came down on my ass. I’d get up, brush off my blood-stained cargo pants and look at my palms, unable to tell if the scrapes had been there or if they were fresh. Blood, scrapes and bruises of indistinct origin just came with the territory.

The trick I remember fucking up most was a backside kickflip down a set of five stairs. For the uninitiated, a few things happen in this trick. The board flips over once while also spinning 180 degrees away from you. Your body spins with it, and the direction in which you turn makes it a blind jump, a bit of a leap of faith. It’s not the most technically challenging or visually spectacular trick, but when done down a set of stairs, it requires either a lack of fear or blunt force stupidity, and I had a little of both.

I was 16 years old, 140 pounds and had attempted this trick somewhere between five and 300,000 times. Sometimes the board flipped too many times; other times not enough. Sometimes my back foot hit the floor but my front foot landed on the board and dragged me into a split. Sometimes I knew from the jump it wasn’t happening and kicked the board out to bail — rolling, tumbling, eating shit. I once landed it but didn’t roll away smoothly, and John declared that it didn’t count as a make.

At no point did any of this feel dangerous. This was how I spent every afternoon of my teenage years. In fact, every memory I have from this period of my life involves either hurling myself off of something or being chased out of someplace. If it was raining, I stayed inside, sat two feet from the TV and studiously watched my VHS copy of Welcome to Hell, Toy Machine’s 30-minute, anarchic skate classic. Even hearing songs from its soundtrack today, I can recall which tricks happen on specific beats. I still wince when I hear D.R.I.’s “Do the Dream” because it reminds me of Ed Templeton splitting his ballsack open on that rail.

When I started skating in the mid-1990s, skateboarding didn’t enjoy the cultural cache it does now. Prior to the early aughts, when Tony Hawk’s incredibly successful video game franchise legitimized the sport in the mainstream, it was considered a dirtbag activity, as many, many of my young romantic interests explained to me. Skateparks, especially city-funded ones, weren’t as commonplace as they are today. Fellow skaters were also rare and hard to find without the connectivity of the internet. If you wanted to locate a place to skate and people to skate with, you had to speak the language. Waxed ledges and scuffed walls were signals to the tribe that an area was skateable. Similarly, any kid who wore sneakers that were completely torn up on one side was a member.

Twenty years and [sheepishly mumbling under my breath] 60 pounds later, skateboarding has fallen by the wayside in my life. Not due to any major injuries, amazingly, but just in the way adulthood slowly steals the fun things that make you happy. Middle managers, W-9 forms, health insurance plans, overdraft fees, parking tickets — these are just some of the thousand-and-one headaches that fill in the cracks formerly flowing with the joy of youth.

And so, when I bought the fresh deck from John onto my driveway, I took a quick glance around to make sure no one could see me. Here’s the honest truth about what happened: Within the first five attempts, I landed a picture-perfect kickflip. And I mean perfect: hard pop, sharp flip, crisp landing. It was like I’d never put it down.

That was the last one I would land for the day, however.

The next 30 minutes saw me sweating and panting through several dozen embarrassingly pathetic attempts to chase that high. My muscle memory for skateboarding is still buried somewhere inside me, below several layers of useless knowledge about adult concepts I vaguely understand like “401(k)s” and “subprime mortgages,” but my muscles themselves aren’t in skating shape.

Gasping for air in the 90-degree heat, I went inside and took an ice-cold shower because sweat felt like it was shooting out of my skin. My feet were swelling from the hard, repetitive landings. My legs were sore and tight in such weird and unfamiliar places afterwards that I didn’t get back on my board for another four days. A man’s thirties are full of humbling little moments of realization that he’s no longer young, and the act of wincing while doing something as basic as sitting down on a toilet is worth about a hundred of them.

I’ve healed up since then, and now add five minutes of stretching to my pre-skate warm-up, something I’d never even considered as a teen and probably would have mocked if it was suggested. I also started filming my trick attempts as I’ve slowly regained my mastery. After I got my kickflip back, I moved onto heelflips, fakie varial flips and 360 flips, which I’ve always struggled with. One by one, my old body has been catching up to my young brain. The landings are rough and rudimentary, I’m not getting as much air as I used to and I require frequent breathers, but it’s satisfying.

John and I exchange nightly video dumps of our accomplishments. We live on opposite coasts, and it’s a nice way to stay connected — not just to each other but to our teenage selves. After watching our clips before I go to bed each night, I flip over to Instagram and scroll through the many skateboarding accounts I follow. Most of them feature pro skaters tearing up steep rails and clearing massive sets of stairs. The one I find most inspiring, though, is called Tired Skateboards, an account that describes its audience as “the guys that are the same age as the security guard kicking you out of the spot.”

It mainly features men of my age and build, having fun landing the basics. Nothing fancy, just meat-and-potatoes skating. A quick 50-50 grind on a curb here, or a little pop shove-it off a short ledge there. It celebrates effort over technical precision, and the comments largely provide positive encouragement. “Nice one!” and “Nailed it, dude!” are common replies. The third-place medal emoji is a badge of honor.

“It’s a skateboard company where nobody tries very hard. If anything is our motto, that’s it,” says Raw Rodgers, a 45-year-old father and skater for Tired. Each Christmas Day for the last few years, the esteemed skate brand Thrasher has thrown Rodgers and Tired a bone by featuring their videos on their website. He lacks speed, his landings are sloppy and he has the balance of a penguin waddling across a slick glacier, but he says the sense of camaraderie he’s found has been worth some ridicule. “For the first couple of years, [the comments were] very negative: ‘Why are these guys on here? He sucks, he’s fat, he can’t do this, he can’t do that.’ But a lot of people now tell me that I’ve inspired them. I’ve had pros that I looked up to as a kid telling me that I’ve inspired them to start skating more.”

I’ve been hearing similar encouragement from my fellow 30-and-ups since I started posting videos of my mild skate achievements on Instagram. My friend Joe Principe, a 45-year-old dad and bassist for the punk band Rise Against, tells me he’s also found more time to pick skating back up during the stay-at-home order and is in the process of building a mini-ramp in the backyard of his Chicago home.

“For your kids?” I ask.

“No,” he responds. “It’s for me and my buddies.”

“There’s a beautiful freedom that comes with skateboarding,” Principe explains. “There are no rules, no limits, and therefore, you can be yourself, set your own rules and learn at your own pace, without ridicule or judgment. It’s why I was drawn to it in my youth, and it still applies in my adulthood.”

I feel that same freedom every time I get on my board. Skateboarding has always been a solitary discipline for outsiders, an individualized activity free of team-sport mentality, but there’s something uniquely liberating about skating in my 30s. I no longer harbor any delusions that I might go pro one day. I’m not trying to earn a sponsorship. I don’t fantasize about hitting El Toro or Lyon 25. I have no goals beyond landing a good, honest kickflip.

Last week, I finally worked my way back up to backside kickflips, the trick that had driven me to madness as a teenager. It’s been slow-going. There’s more of me to spin around these days, and more fear of that blind landing. With each attempt comes a sudden flash of every hospital bill I’ve ever paid since leaving my parents’ insurance. Nonetheless, I devoted a very sweaty hour yesterday solely to getting this trick down. My wheels squeaked and squealed and again informed me that I’d fucked up. A few times I fell flat on my ass with the grace of a beefy toddler getting toppled by an ocean wave.

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Then, on my fifth or sixth “last try,” my legs and my brain shared a rare moment of perfect synergy. I popped up, spun around, and when my body completed its rotation, my flipping board was waiting right under my feet. I landed and rolled away clean. I wish I could say that my days of hard work had paid off, but really, it felt beyond my control, like a younger version of myself had briefly taken over.

It wasn’t down a set of stairs, but it was good enough.