How High Maintenance Creates Ethical Tension

The fourth season of the HBO show questions its own charming vision of urban coincidence.

Ben Sinclair in 'High Maintenance'
High Maintenance paints NYC as a mystical ecosystem. (David Russell/HBO)

As the highbrow salad chains that have gobbled up Manhattan pursue the exclusionary dream of a cashless society, TV’s loveliest vision of New York City still indulges the romance of little green bills. In the second episode of the fourth season of High Maintenance, the show’s star weed dealer (“the Guy,” played by Ben Sinclair) refunds a few bucks to a client whose rug is soiled by the Guy’s dog. That client hands an envelope of money to a sex worker, who later gives the envelope back after their hookup turns out to be more gratifying for him than for the man who hired him. That sex worker, who’s also a waiter, waits on a table that undertips him—but the undertipper returns later with cash to atone, and the waiter then offers to buy her a drink. Money moves across these stories less as a currency than as a proxy for goodwill, and the fuzzy mantra “Pay it forward” starts to feel concrete.

In this and so many other ways, High Maintenance paints NYC as a mystical ecosystem. Though the Guy is never far from the action in the masterful web series–turned–HBO comedy, the focus is always on a few different onetime characters. Bodega clerks, actors, construction workers, yogis, yuppies, nudists, Women’s Marchers, Republicans, Hasids, nuns, children, and almost any urban life-form you can name putter briefly in and out of one another’s lives, creating little collisions that yield tension and, fleetingly, connection. These diverse individuals are sketched with such fine-point details—meandering and mumbling as if in a documentary—that it feels plausible when they’re knocked into someone else’s orbit. It feels plausible, too, that most everyone turns out to be a fair and generous person.

There’s a seductive message in all the serendipity. In The New York Times Magazine last month, Willy Staley argued that the series’s pageant of healthy cross-tribe interactions soothes an audience made up, in significant measure, of gentrifiers. “While New York is still the pleasure dome that less ethically burdened depictions (Sex and the City, for example, or even Girls) made it out to be, it’s no longer quite so easy to enjoy without reservation,” Staley writes. “There is some sense that this all comes at a cost—one that mostly falls on others.” The remedy from High Maintenance—and contemporaries such as Russian Doll and Master of None—is to portray the Big Apple as “a moral training ground—for protagonist and viewer alike,” Staley writes. The stereotypical High Maintenance viewer spends his or her evening shut away from neighbors while bingeing on depictions of a city that “forces you to become a better version of yourself, the one where strangers come together and connect.”

Staley hit upon a key appeal of High Maintenance (a show he, overall, praises). Yet his analysis carries the radical implication that something about this social moment makes it wrong to pair dramatic catharsis with a realistic aesthetic. After all, if High Maintenance has a balming effect, that’s in part because it’s doing what almost all TV ends up doing, which is creating a satisfying narrative. You meet a character, and you expect that character to go on a transformational journey that leaves everyone okay. Real life, in general, doesn’t move in short, interesting arcs; actual strangers tend to stay strange. As High Maintenance sorts through the chaos of city life and examines the most intriguing characters it finds, it educates and creates empathy—but also commits voyeurism, contrivance, and feel-goodism.

To acknowledge that dynamic does not undermine the greatness of the series; rather, it strangely deepens it, because you’re then meeting the show at its own level. No one is cannier about High Maintenance—and the urban-explorer genre it traffics in—than High Maintenance is. As it nests stories within stories, or daisy-chains them together, it continually checks its characters on the validity of the stories they tell themselves about their own life. Often, the action is in watching characters’ personal set of ethics meet up with the reality that the people around them are, whether or not they always recognize it, living out their own narratives and values. It asks, again and again, what storytelling is for, and it’s okay with an ambivalent answer.

It’s fitting that the fourth season begins with a coastal-elite crossover event: High Maintenance meets This American Life. The first episode depicts a programming meeting of the legendary public-radio show, where a mix of actors and real-life staffers—including Ira Glass—pitch story ideas on the theme of “recycling.” One person, Yara (Natalie Woolams-Torres), volunteers a tale about her parents breaking up and getting back together. Glass loves the idea and asks if her parents would be willing to talk. Without hesitation, she answers yes.

Her parents aren’t willing to talk, though. Yara calls both of them individually, and they firmly say that they want to maintain their privacy. It’s a setback, but she has an idea for a way forward on the story. While getting stoned with her boyfriend, Owen (Marcus Raye Pérez), she starts recording her own thoughts about her parents’ relationship. Her monologue wends its way to addressing her own life and her romance with Owen, who she implies is a good match for her because, as a nurse, he’s unambiguous and “safe.” Owen is offended. The ensuing confrontation ends up on tape, including the part in which he calls her out on taping him: “Are you fucking kidding me with the mic?”

Here High Maintenance is picking at the question of how much reality can or should be harvested for content. Yara at first seemed to have hit upon a lucky linkup between her personal life and her job. But her efforts to tell her parents’ tale hit up against her parents’ prerogative to keep that tale to themselves. Then, by raiding her own life—and by imposing grand, explanatory narratives on a complex relationship—she ended up alienating the person closest to her. Yara comes off as smart, idealistic, but a bit self-involved, and it’s clear her careerist-slash-creative desires have hijacked her decision making. In the next editorial meeting, she plays the audio of the fight—including Owen’s objection to being recorded—and reveals that she and her boyfriend aren’t talking anymore. (This plotline was inspired by a real This American Life segment in which a producer fought with her husband on tape.)

The twist is that her ethically dubious efforts don’t even pay off. The other radio producers deem the audio of Yara and Owen’s fight riveting but say it doesn’t rise to the level of compelling narrative worth broadcasting. For a moment, it appears Yara’s attempt to commodify real life has been entirely catastrophic—personally, morally, and professionally. Through the critiques from Glass’s staff, High Maintenance has made the case for why it so often bends messy reality into a pleasing beginning-middle-and-end story. Yet in the consequences for Yara’s life, it has also spun a fable about the exploitative potential of the work the show is constantly engaged in.

But then comes the patented moment of grace. The episode’s B-plot follows Arnold (Larry Owens), who performs the grueling job of putting on costumes and singing personalized telegrams to the likes of birthday havers and test takers. The trials Arnold goes through—which primarily involve not having a reliable bathroom to use while shlepping around the city—make for a madcap, stressful interlude. At the end of the episode, Arnold, costumed as a big, broken heart, barges into Yara’s disappointing editorial meeting. He’s there to deliver a song from Owen, who wants to reconcile. Glass and the other radio producers giggle and grin—and record the moment. Later, Glass interviews Arnold for a segment about his career as a singing telegram. The alchemizing of real struggle into content has been interrogated enough for one episode of TV. It’s time to perform the alchemy itself.

This season’s second episode—the one with all the cash trading hands—also engages in some brutal self-reflection on the way to uplift. Its vessel is the new character Kym (Abigail Bengson), who works as an intimacy supervisor for film and TV. The gig is a novel but real one, emerging in the #MeToo era to ensure sex scenes are filmed in a manner that is respectful to the actors. To add to the meta: HBO has been at the well-publicized forefront of the Hollywood shift toward using intimacy supervisors.

When viewers meet her, Kym is shaping a hookup scene in a Scandal-like political drama by coaching the actors on where to place their hands. She also influences the onscreen storytelling by endorsing choreography that makes the female character appear to have more control in the encounter. Later, Kym participates in negotiations over nudity clauses in actors’ contracts, and she hands out chapstick to actors about to simulate making out. All this scut work is implementing a set of values. As she explains at one point, “If it’s not good for you to have your breast touched or your butt touched, for whatever reason or for no reason—and you don’t have to tell me the reason—then guess what? You don’t have to have your breast touched or your butt touched. We will find another way to tell the story.”

That take on storytelling sounds admirable. But High Maintenance goes beyond depicting a respectful new normal. It asks whether and how the ethics preached by the progressive entertainment class carry over to its members’ personal lives. Kym hits it off with Evan (Avery Monsen), a magician hired for a bit part on one of the sets she’s working at. They go on a date during which Evan reveals that he is asexual. Kym is taken aback and, clearly, a bit disappointed. But she nevertheless thanks him for sharing, asks him questions (he’s asexual but not aromantic, it turns out), and later agrees to go on another date with him. As they sit down for that date, she playfully touches Evan’s leg. Clearly shaken by the physical contact, he darts from the restaurant.

The moment when Kym’s sitting alone, wearing a worried smile and processing what just happened—did she just violate someone else’s consent?—is excruciating and believable. Happily, Evan ends up returning to the restaurant and apologizing for overreacting. He and Kym start to talk about what his boundaries are and what her needs are. (“If you can’t hug me, if you can’t hold me, or hold my hand …” she says, trailing off. “I don’t mean that you have to do it now. I can be patient.”) And they come to a sweet, if awkward, resolution, with him caressing and then kissing her wrist—something he says he’s never done before. From the swirl of city life came a test for Kym’s most highly touted principles, and though she didn’t pass the test flawlessly, in the end, all is fine.

Notably all is fine not only for her, a well-educated white woman, but also for the characters squeezed more intensely by the city’s rising cost of living. That fineness, however, in part results from the decency of the gentrifier types onscreen. Kym is the undertipper who returned to make good with a waiter, who, the audience knows, is a black queer sex worker. Arnold, a black artist living in cramped quarters and hustling to stay afloat as a singing telegram, plausibly has a chance at a bigger break by being featured on This American Life. The way in which disparate characters luck into symbiosis would seem hopelessly facile—if the show didn’t also seem to acknowledge, with plot material about the horrors of the gig economy and other features of modern capitalism, that structural problems outlast individual moments of grace.

Indeed, the poignancy of the show comes from the fleeting nature of the happy accidents it stages. What High Maintenance is really doing is trying to wring small amounts of social awareness out of the precious fact that cities remain, even now, coincidence machines. As I was working on this very article, I hopped on the subway, and standing next to me was Ben Sinclair, the High Maintenance co-creator and star. His AirPods were in; he was reading a book; l gawked and didn’t approach. Did any greater understanding—of society, of the show, of anything—result from running into the stranger-celebrity I’d been writing about moments before? Only this: A city of 8.6 million people can provide a neat ending to any story.