Shasta Fay Hepworth and I were introduced to each other at a party back in my hometown of Austin, and right away it was obvious that we were both into each other. She was beautiful (hazel eyes, a thousand-watt smile) and witty. She had many of the same interests I did (books, writing, sports) and a few I knew nothing about (dressage). Twenty-eight years old, she taught high school chemistry, and made bad scientific puns. She was too good to be true. I got her number, and we’ve been texting ever since. (more…)

Recently, Katja Blichfeld and Ben Sinclair, the married co-creators of the web series High Maintenance, were exiting the Atlantic Avenue subway station when they saw an unassuming, middle-aged woman, begging passersby for money, cigarettes, or MetroCard swipes. “She looks like a Park Slope librarian,” Sinclair tells me, recalling the sight. Or: “Your aunt who just lost her job at a school board in Pennsylvania.” It took a moment for the face to register, but when it did, Sinclair turned to Blichfeld and said: “It’s her! It’s her! It’s Heidi!” 

“Heidi” is Homeless Heidi, a character in an episode of High Maintenance who dates men in order to use their showers and take their money. She is based in part on the woman outside the Atlantic Avenue station, a grifter who’d stayed with at least two of Sinclair’s and Blichfeld’s friends, and whom the couple had seen countless times around the borough over the last five or so years. “I think she prefers to beg,” Sinclair says. “We watched her for a while.”

Another inspiration for the character was Sinclair himself, an actor whose bushy beard often got him cast as down-and-out characters on network TV shows. Creating characters out of a combination of personal biography and close observation: That is the formula High Maintenance has employed to great success, over 13 episodes so far. “When I was a kid, I used to play a game with my mom where I would imagine lives for strangers we would see,” Blichfeld tells me. “I think we still do that, only now we put it on paper and dramatize it.”

High Maintenance utilizes a simple but effective narrative structure, following an urban weed dealer, played by Sinclair, as he delivers to customers across the city. Each episode focuses on a particular customer, and by extension, their living space, where the deals take place. The setup enables minor intrusions into the private lives of New Yorkers, in all their neuroses, personality quirks, and messiness. Sometimes the dealer sticks around to smoke, or eat, or, in one case, help dispose of a mouse caught in a glue trap. Other times, he is in and out in the time it takes to complete the transaction. “We wanted to portray a situation that could unfold in real time,” Blichfeld says, “and in our experience, a drug deal usually takes just a few minutes.” The decision to make the protagonist a weed dealer as opposed to, say, a pizza delivery man was an easy one. “It’s just a sexier concept,” Blichfeld says. “And pizza men don’t get invited past the threshold, except in porn movies.” Or, as a character in the first episode puts it: “When the guy who delivers my Pad Thai comes, he doesn’t inventory my personal belongings.”

The show is funny, but it steers far away from the traditional stoner comedy tropes. There is no burnout philosophizing, no excessive snacking, no MacGyvered ad hoc contraptions for smoking, save the occasional appearance of an apple pipe. Rather, High Maintenance treats its characters and its setup without a trace of caricature; these are ordinary people, just trying to deal with their lives. “We don’t need to write about the fact that people smoke pot,” Sinclair says. “The more interesting thing is, why do people smoke pot? Or, what are the circumstances around it?”

By inviting the viewer inside characters’ homes and lives, the show appeals to the empathetic voyeur in each of us—a compassionate curiosity that might just be the natural response to living in New York. City dwellers, especially here, seem intensely private and protective of personal space, and yet we’re outwardly focused, constantly studying strangers on the sidewalk and subway. We want to observe, but not be seen staring. “We’re fascinated by how you can look around a train car and see all these people shoulder-to-shoulder, not looking at each other,” Blichfeld says. “In this city, people are all in their own worlds, but they’re touching. It’s bizarre that we do that.”

A drug dealer is one of the few people who moves freely between these two worlds, the public and the private. In High Maintenance, the dealer is an unnamed character referred to only as “The Guy.” Few biographical details are hinted at, though in early scripts The Guy had an entire backstory. “But it just wasn’t as interesting as what we imagined the viewer could imagine for him,” Sinclair says. By leaving him blank, The Guy becomes the transparent eyeball of the viewer, the unobtrusive vessel by which we gain access to the inner sanctums—and thus, the private lives and personal problems—of strangers. This access satisfies our urge to look; what we see is human struggle, and it is never less than mesmerizing. Sometimes, the problems we see are banal, as in the episode “Trixie,” which focuses on a young couple who rent out their loft on Airbnb because they’re “trying to live like adults this year.” Other times they are profound, as in “Jonathan,” when comedian Hannibal Buress witnesses and is traumatized by a shooting at one of his shows, or in “Brad Pitts.”

“Most of our episodes have a theme of people trying to stay optimistic in the face of adversity,” Sinclair says. “When you live in this city, one day of the week is going to be the worst day of your life, and one day of the week is going to be the best day of your life. And that’s kind of what it’s like to live here. That’s why New Yorkers are really nice to each other when the shit hits the fan—there’s a community centered around suffering.”

Sinclair and Blichfeld claim solidarity with their characters, many of whom are middle-class artistic types striving to maintain as much as advance in the world. The couple married on New Year’s Eve, 2010, and the next year started writing the character sketches that would become High Maintenance. “An enjoyable evening for us is hanging out with friends and telling stories,” Sinclair says. “A couple of years of that turned into this TV show.”

Blichfeld is an accomplished casting director—she won an Emmy for her work on 30 Rock—and Sinclair is an experienced actor and editor who taught himself filmmaking by entering spec commercial contests online. They had all of the skills and contacts to make a successful show, but little of the money. So the first 13 episodes were mostly shot in friends’ apartments, with actors the couple knew socially. “We wanted to keep it low-stakes for ourselves, and see if anyone would even watch it,” Blichfeld says. “We all just got to hang out and make some movies together—that was good enough for us.”

The episodes were released in batches on Vimeo, where they stream for free. Each is between six and fifteen minutes long, and although a few characters appear in multiple episodes, the plots are non-contiguous. They’re like short stories, demanding little but rewarding thoroughly. No detail is wasted.

“It’s hard to tell a satisfying six-minute story,” Sinclair says. “When we sit down to write, the satisfaction comes from the intricate braiding of all these different elements, and I didn’t wanna make no prairie braid all day—I wanted to do a double fishtail! But we have to be very judicious editors. If you’re trying to take someone from A to Z and you only give them A, D, M, P, R, V, they’ll still know it’s the alphabet.”

Late last year, Blichfeld and Sinclair had discussions with FX about bringing High Maintenance to cable, but ultimately the couple signed with Vimeo, who provided financial backing for six upcoming episodes. “They have been really cool,” Blichfeld says. “They haven’t put any restrictions on us at all. We’re like their artists-in-residence.”

Staying with Vimeo allowed Blichfeld and Sinclair to keep High Maintenance the same show it’s been, only a “little bit supersized—more locations, more cast, more scenes, more setups.” The new episodes will be released in two batches: three sometime in November, and another three in early 2015. For the first time, viewers will have to pay to watch, although pricing hasn’t yet been determined.

Following our interview, Sinclair and Blichfeld were heading back home to complete editing on the final two episodes. I ask what they look for when they’re editing—how do they maintain the meditative, languid pace and the finely drawn character portraits that mark each episode, without revealing too much?

“We like to keep it real blurry,” Sinclair says. “Literally and figuratively—sometimes, the image blurs on our show, and that’s intentional. We like blurred lines.”

“Not the song,” Blichfeld adds. “Although that’s interesting, because I just read that Robin Thicke was really stoned when he recorded that song.”