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I own a chameleon, eat paleo foods, write dumb stuff online, and watch the Bachelor franchise. I'll occasionally exercise, and I recently started an acupuncture practice, but the latter just requires me to lie still and the former is becoming increasingly infrequent. A month ago, however, I was struck by a vision of myself wearing some kind of fashionable hat while gliding down the street on a skateboard.

I immediately knew that I had to become the person in my mind's eye. Maybe once I did, I wouldn't be as deeply depressed, neurotic, or focused on a high-fat, low-carb diet. But before that, I would have to suffer through the indignity of working at it. Skateboarding seems like the ideal thing to decide to do when you're freaking out about your life. Dan Meyer, a seasoned skater who works at VICE, where there are many seasoned skaters, put it this way: "There's no coaches. No parents." There is one rule, though: It's kind of embarrassing to be over the age 14 and learning how to skateboard for the first time. Luckily, my adult boyfriend, Rion, and my adult roommate, Spencer, also decided that they wanted in on skateboarding's transformative powers, so I had a crew to dull the shame of running into a group of teens—they're always in groups—who are better than me at skateboarding. Rion, Spencer, and I walked to our local skate shop as a united front in order to pick out our boards. From the perspective of an adult having a quarter-life crisis, the inside of a skate shop is very scary.

There are young people picking out boards confidently. There are relaxed salespeople (all men) in crewneck sweatshirts who "hang back" until you approach them, and you are not going to want to approach them because you're embarrassed. After about 15 minutes of staring at the selection of standard decks, which were all confusingly different sizes but only by centimeters, Spencer finally asked for help: "Hey, so, we're adults and we want to start skateboarding. What do we do?" The clerk did not even smile at my roommate's attempt at humor. It's not that he was unfriendly—it was more like he probably hears this inquiry at least once a week from neo-yuppies who had shelved their vague desire to "be an artist" and suddenly realized they've become boring. The clerk explained that the board sizes don't really matter because we're likely not doing any advanced tricks (roasted) so we decided to choose decks based on aesthetics. I got one that had "Lizard King" written as if it was spray-painted in lime green caps amid a purple, sparkling background as an homage to my chameleon, Drake. With the trucks, wheels, and grip tape—the existence and names of which I learned that day—it cost $150. A small price to pay, I thought, for my awesome new life. I would later learn that "Lizard King" is the name of a current skater, and the board I picked was "his" board. For a second I felt like a poser, and like I should immediately start working to become Lizard King's biggest fan, but I eventually let that go. I made up my mind to reclaim the name for actual lizards, and even when a friend mentioned to me that my board-sake recently appeared on VICELAND's skate-competition show King of the Road and pooped into a shoe, I remained unfazed. Rion got a board that had drawings of lizards on it, and Spencer declined to get a board because he got cold feet and started to fear that he would rapidly lose interest in skating. For the next few weeks, my crew and I would walk at least four blocks away from our apartment so our neighbors couldn't judge us and practice. (Spencer used an old board that my boyfriend had acquired at some point in his life courtesy of the brand Zico Coconut Water, and we called him "Zico boy" to shame him.) For added drama, we brought a small speaker with us and played Blink 182 songs. Rion and Spencer both skated when they were younger, so they had the basics down. While they were testing out rolling ollies and kick-flips, I would ride up and down the street trying to get the hang of it. After I spent a day learning to simply stabilize myself, I found out that skating—as in being able to stand on a board, push yourself forward, and coast—is kind of easy. My next hurdle became learning to turn around smoothly. When you're riding, you can pretty much lean from side to side to maneuver. Doing a full U-turn, however, is a bit more difficult. I spent hours just working on pushing down on my back foot while lifting up with my front foot to "scoot" the board in a circle without falling down, which I did a lot. Whenever I got bored with that, and a little jealous of the boys' fun, I would attempt an ollie. I'm happy to report that within a few days I achieved what I'm calling "a cute baby ollie," in which I actually got a wisp of air beneath my back wheel!

I was starting to feel really good about my new life as skater. Dressing like a skater essentially means wearing flat shoes and T-shirts. Also if you're wearing shorts, you have to wear high socks, I guess. From what I've gathered, it's all about appearing strategically shitty. Comfort is also key, but a lot of skaters bafflingly wear skinny jeans. Not to brag, but I pretty much already had a cool skater vibe going in my day-to-day wardrobe—during the winter I exclusively wore Converse, sweatshirts, and baggy pants because I was too depressed to look nice. The only thing I needed was a faddish hat; I decided on a red bucket hat because, out of all the hat styles, it made my hair look the least stupid underneath. If my hair was longer, maybe, I wouldn't mind going for the dad-hat look. For extra flair, I also bought a Vans T-shirt with an iguana on it to compliment my board and my overall brand. Now that I was presentable, I was ready to go to the big show: the skatepark.

If I had to describe the skatepark in only three words I would go with "hats" and "boy city." There are so many hats and boys! When I arrived to the scene, teens lined every concrete surface, taking turns dropping in on the ramps, grinding on the rails, and jumping over stuff. She had dreads, and was wearing wire-rimmed sunglasses, a grungy tank top, and blue track pants—a surprisingly good look.


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