Art continues to imitate life in ‘High Maintenance’ Season 4

I was introduced to High Maintenance through a friend after a particularly crummy day. In an effort to make me feel better, she put on “Museebat,” an episode from the series’ first season that follows a Muslim girl navigating religious customs and familial obligations as she enters college, and a group of swingers who realize they might have contracted an STI.

Both plotlines were radically specific, and although I couldn’t relate directly to either set of events, the series felt intimately relatable because it felt so real. Each character reacted like a real person might, and their motivations were ordinary and understandable. A few scenes were completely silent and depicted a solitary moment in a particular person’s particular day, underscored by fragments of conversations and passing moments.

Such lifelike, original stories portrayed onscreen soothed me, and I was struck by how effortlessly human the series was.

For those not familiar with the series, each episode of the show focuses on two New York City-based storylines that tend to intertwine indirectly. The series has two, overarching constants: The Guy, portrayed by co-creator Ben Sinclair (co-creator Katja Blichfield has appeared in two episodes), a kind, happy-go-lucky weed dealer who traverses the five boroughs on his bike; and subtle, patient depictions of beautifully mundane occurrences (like this one). Episodes are built around a host of non-recurring characters in the High Maintenance universe that The Guy either deals to or merely crosses paths with.

Woolams-Torres and Ira Glass, who guest stars as himself in the fourth season premiere. Credit: david russell/hbo media relations

Even though I’ve become a High Maintenance devotee, the first two episodes of the series’s fourth season exceeded my expectations. “Cycles,” the premiere episode, follows a WBEZ This American Life reporter named Yara (Natalie Woolams-Torres) mining her personal life for a story. When examining an anecdote about her parents' marriage, Yara realizes she’s been looking at her world through rose-colored glasses.

In a vignette of 15 minutes or less, High Maintenance succinctly captures the lingering aftershocks of transitioning from childhood to adulthood that occur throughout one’s late 20s and early 30s. Yara coming to terms with the underbelly of her parent’s wavering partnership is low-stakes, but it’s painful nonetheless; the episode is devoid of tragedy, but the viewer winces at the familiar melancholy of Yara’s rite of passage.

Yara’s story is complemented by the daily tribulations of an exhausted singing telegram performer (Larry Owens). Owens is impeccable comic relief, and his delivery of a multitude of jingles is magnificent -- and, as is characteristic of the series, his character helps resolve Yara’s emotional disorientation. (Also, The Guy bumps into a stray dog and whimsically decides to take care of it, which is adorable.)

Owens dressed as Marilyn Monroe for a birthday-themed telegram. Credit: David russell/hbo media relations

"Cycles" sets the tone for the forthcoming season by continuing High Maintenance's legacy: It's compassionate, messy, self-deprecating, revelatory, and life-affirming.

The fourth season's second episode, “Trick,” presents Matthew (Calvin Leon Smith), who is in search of affection and hires an escort (Jay Jurden); and an intimacy coordinator named Kym (Abigail Benson), who explores the particular physical boundaries of a new romantic prospect (Avery Monsen). Orbiting its theme of orchestrated and unconventional intimacy, “Trick” gives viewers a behind-the-scenes look at a topical profession, and how (and why) intimacy is negotiated beyond film and television sets.

The series tackles such incredibly delicate issues with dexterity and caution, and "Trick" exudes a quiet sweetness while examining loneliness and all the sparks involved discovering a kindred spirit. There are many High Maintenance characters I'm glad to be through with after their half-episode arc, but I'd watch a whole season devoted to Kym and Henry. They stumble through their budding situationship, and it's meaningfully raw, singular, and pure.

High Maintenance is unique in that it doesn't attempt to soar to new, dramatic heights with each coming episode or season. On the contrary, the series' beauty and grace lie in its ability to evoke an empathetic response from viewers, and following The Guy on his journeys grants a brief foray into the lives and worlds of (fictional) others as a brief respite from one's own worries.

What's more, the series sends a message that to be human is to learn about oneself and, in turn, relate to others. Both "Cycles" and "Trick" communicate that message, and I'm looking forward to what the rest of the series's fourth season holds.

The fourth season premiere of High Maintenance airs on HBO on Feb. 7, 2020.