Season 3 of High Maintenance Retains the Show’s Unique Intimacy


Both literally and figuratively, High Maintenance strips people down. The first episode of the third season, which was released on January 17, opens with a naked old man transporting a pot of boiling water through his dark house. We keep our fingers crossed that he doesn’t spill it all over himself as the walk stretches on, but he makes it to the bathtub. Slowly, he lowers himself into the water, lights a joint, and, in a slow build of white light, dies.


We are invited to his wake, where a large group of his misfit friends play bad music together. We watch as one of his closest companions sits, fully clothed, in the tub in which he died. She hallucinates that he is watching her from the doorway. This happens slowly, without explanation or analysis; we are supposed to contemplate her grief rather than understand it. Ultimately, High Maintenance manages to expose people without the judgment that might come with it.


First launched as a web series in 2012 and picked up by HBO in 2016, the series has become a cult-favorite. Each episode tells a new story of someone living in Brooklyn, from nudists to high-strung parents to an agoraphobic. One of my favorite episodes, “Grandpa,” is told from the perspective of a dog. The one thing that connects all of these characters is their shared weed-dealer. (Except the dog, he doesn’t buy drugs.) The character’s shared dealer is known only as The Guy and is played by Ben Sinclair, OC ‘06. The Guy delivers to his clients in their homes; we are pulled into whatever happens after he leaves.


High Maintenance was created by Sinclair and Katja Blichfeld, who had previously worked as an Emmy award-winning casting director for 30 Rock. The two were once married, but made the decision to get divorced on election night of 2016. In a 2018 profile by The Cut, Blichfeld discusses the breakup, which was partly prompted by her realization that she wanted to be with women. Blichfeld had dated women before, but she had also been raised as an Evangelical Christian, and struggled with accepting her sexual orientation. The Cut writes, “Sinclair, though upset, was not surprised. (‘I mean, he went to Oberlin,’ [Blichfeld] says.)”

Much of the show’s fundamental intimacy is borne from Sinclair and Blichfeld incorporating their personal experience into the series. This is especially evident in season one, which explores a lot of fractured relationships. In “Meth(od),” two best friends, who are also pretty terrible people, come close to losing each other; in “Museebat,” a woman tries to prepare a 50th birthday party for her husband, but they’ve been fighting nonstop. Later in the season, we learn that The Guy lives down the hall from his ex-wife, Julia, who is now dating a woman. After The Guy gets in a bike accident in season two’s “Scromple,” Julia keeps him company.


This type of transparency is part of what makes the show so unique. Sinclair and Blichfeld don’t seem to be holding much back from the audience; they translate what is happening in their real lives into their work, making it feel particularly authentic.


Vulnerability is a large part of the show. This comes, of course, from the basic premise: the relationship between a weed dealer and his clients is one based in secrecy and trust. The Guy is a neutral figure, sometimes developing friendships with his clients but mostly participating as a professional, silent presence. His impartiality opens up room for people to feel comfortable telling The Guy whatever is on their mind, often leading to oversharing that The Guy allows but doesn’t reciprocate. From there, the stories are based on a trust between viewer and character; we, as the audience, take on the neutral position of The Guy after he leaves. We watch these people at their most strange and private.


As a result, High Maintenance is highly non-judgemental and inclusive, and shows us that people are often much more complicated than they seem. In “Derech,” Anja is an invasive journalist who sneaks her way into a support group for former Orthodox Jews for a Vice story. But rather than this being a story of exploitation, it turns into something else when the plot line gets tangled up in another involving drag queens and a near-death situation. We are reminded that we never know what will happen until it’s actually happening.

So far, season three still holds onto many of the things that make it so great. The episodes are insightful, unassuming, tinged with humor and absurdity. Things are a little different, though; The Guy, fresh off of a breakup from the previous season, now drives around in his van rather than on his bike, and takes frequent trips upstate. In the first episode, we see him driving down wooded roads and paddleboarding down a secluded river. He meets a woman and we realize that he is trying to figure his own stuff out. He’s in his thirties now - is he going to deal weed forever? The third season is trying on a different kind of intimacy, then, because we still don’t actually know the main character. Just as he flits between clients, The Guy has also been eluding the audience. Now, though, we are being let in.

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