This HBO Show Is a Super Awkward Love Letter to Humankind...and I Can't Get Enough

I’m currently in the process of testing GPS running watches for a different PureWow article and as such have been running through Central Park with six watches strapped across both wrists. When I told my sister other passersby must think I look nuts as I frantically try to start and stop all six at roughly the same time, she replied, “I mean, you’re definitely not the weirdest thing they saw in the park that day,” and she was absolutely right. Just last week I saw a guy out for a jog with a pig on a leash. And no one else around me was even fazed.

These charming oddities of human nature are at the center of HBO’s wonderfully weird new docuseries, How To with John Wilson, which plays like an incredibly awkward love letter to humankind. Or an amateur anthropological study. Or a how-to guide on the unspoken rules of society. As Wilson himself admits in the trailer, “HBO is having a hard time explaining what my show is.”

Wilson’s darkly funny six-part series features a hodge-podge of clips filmed all around New York City pre-COVID-19, as well as a few other destinations, like Cancun, Mexico, and Ketchum, Idaho, stitched together to form something of a common theme for each episode. For instance, episode one “How to Make Small Talk” includes clips of Wilson attempting to connect with strangers he meets at a travel agency and on vacation at MTV’s Spring Break. “It’s kind of like that show Planet Earth but if it was only in New York and David Attenborough was forced to film everything himself,” says Wilson.

I sat down to watch having no prior knowledge of what this show might be like (it was recommended by a friend as “fun” and I took his recommendation at face value with no further questions) and proceeded to stare, mouth agape for roughly 10 minutes before I decided, “Yeah, this is super funny.” It felt like I was people watching at a cafe with a friend, someone with whom I was sharing experiences that were hilariously charming in the moment but when recounted later would inevitably end with one of us saying, “I guess you had to be there.”

Of course, part of the reason I loved it so much was because, after a year of quarantining, I genuinely miss interacting with other humans, and not just those I know and love. I miss being on the subway and making accidental eye contact with a rabbi who also finds this accordion player’s rendition of the Star Wars theme to be surprisingly good. I miss the friends of friends, quasi acquaintances and near strangers I share a coffee shop with more than I ever thought I would. How To with John Wilson feels like time traveling back to a New York where encounters with all those people are still part of day-to-day life, for better or for worse.

At times, the footage and conversations made me want to cringe or look away. They’re too honest or awkward, in the same way I first found the silences of The Office to be unbearable to watch. It doesn’t help that the camera acts as the viewer's eyes, meaning the folks talking on screen appear to be talking directly to you. In the first episode, there’s a lengthy conversation with a guy named Chris full of awkward silences and shocking conversation twists, kind of like a blind first date. But just like in real life, you adjust and push through, often finding a sweet reward or small treat on the side other. (Chris went from being a silly bit of entertainment to a person I genuinely felt for, so much so that I Googled him after the episode to learn more about how he’s doing.)

You don’t have to be a New Yorker to appreciate How To with John Wilson, but those who know the city well will find it particularly fun. The end of each episode will leave you feeling uplifted and charmed by Wilson and his chosen subjects, so if you’re looking for something more lighthearted than psychological dramas or true crime docs, I highly recommend giving this a try.

PureWow Rating: 4 Stars

This show isn’t for everyone (some will find it just too weird or too awkward), but it’s beautifully done and, in my opinion, just the kind of ode to humankind we could all use right now. If you liked Netflix’s Pretend It’s A City with Fran Lebowitz or Nathan for You, you’ll likely enjoy How To with John Wilson.



Abby Hepworth is an RRCA-certified running coach who has worked in fashion for over 10 years. Want to know what shoes are in this season? She's got you. Need recommendations on...