When they married, Ms. Blichfeld, now 39, was a network casting director for “30 Rock” and other shows, while Mr. Sinclair was a struggling actor getting cast as “homeless man” and “wild-eyed guy,” freelance editing and making attention-seeking videos, including one in which he dances naked through the city to electro-pop. They created “High Maintenance” in part to showcase his intelligent, funny, charming side. Soon they became a poster couple for successful work-life partnerships.
It wasn’t clear if that relationship, or the critically beloved show, could survive their uncoupling.
“If we were not contractually obligated for Season 2, I do wonder what our creative or personal life would be,” said Ms. Blichfeld, who has since come out as lesbian and is dating a woman. “I’m sort of impressed that we were able to work together this year.”
In what Mr. Sinclair likened to “exposure therapy,” they worked side by side after their breakup for up to 15 hours a day, almost every day, for months, writing, shooting and editing the new season. He was also adjusting to the increased workload, responsibilities and stakes of an HBO series. “This year was, like, Season 2 of our show and the Trump administration and our breaking up and giving each other space while still working together,” Mr. Sinclair said. “It was intense.”
Thus, the R.V.
An Almost Midlife Crisis
Making a wide turn onto Atlantic Avenue, cuing up a music podcast called “Chances With Wolves” and heading for the expressway, Mr. Sinclair said he was at loose ends in other ways. The day before, his landlord had informed him that he had to vacate the apartment he once shared with Ms. Blichfeld. The building was being sold.
“That apartment is the last part of my relationship with Katja,” he said with a hint of melancholy. But seeking to put a positive spin on his eviction, he added: “I’m welcoming the forced change. My luck has been impeccable. If I take anything from my life, it’s that.”
“High Maintenance” has benefited from lucky timing, too. It debuted as a Vimeo web series the same month that Washington State and Colorado passed measures to legalize marijuana for recreational use, when every media outlet was doing think pieces about changing attitudes toward pot. America was ready for a kindhearted weed dealer.
But it also resonated because of the writing, which has the subtlety and surprise of great fiction, and because it refuses to mine stoner culture for cheap laughs of the “Up in Smoke” variety. The Guy’s clients run the human spectrum: an agoraphobe starved for connection; a woman fighting cancer; bougie married swingers; a father retired from corporate life living below his high-strung daughter — all of them turning to pot in anxious times to “find equilibrium,” as a New Yorker review put it.
What’s more, every episode is chock-full of Tom Wolfe-ian status details recognizable to anyone living in modern Brooklyn or places like it. The Elena Ferrante book that shows up in three different apartments; the vintage film cameras on a hipster bachelor’s shelf; the precious baby names like Persimmon; the references to intersectionality and illegal Airbnbs. The mellow way these cultural signifiers are treated, however, results not in an acid satire of progressive boho urbanites, but in an affectionate sendup.
In real life, Mr. Sinclair will utter a statement like “My ayahuasca shaman says New York shrinks your aura,” and then, as the show would, do a little eye roll to acknowledge the absurdity.
Given all the emotional turmoil in his personal life, Mr. Sinclair said it was hard this past year to keep the light tone and “not to put some of that bummer feeling on my character.”
But, he said, “people didn’t want to see The Guy in pain.”
To do so would both upset the central conceit of “High Maintenance,” which has always focused on the lives of the clients — not the dealer — and puncture a fantasy. The Guy spends his days cruising around on his bike, having aimless conversations, toking on the job. He doesn’t appear to have problems, only to soothe the problems of others, with his case of goodies and friendly, nonjudgmental patter.
For viewers living in brutally competitive, increasingly unaffordable, class-stratified New York (or Los Angeles, or San Francisco, or wherever), a throwback slacker offers escapist joy.
Which is why it came as a shock when The Guy got robbed and locked out of his apartment in the Season 1 finale, and, intruding on the woman with whom his ex-wife is now living, chucked his phone in frustration over his bad night. Whoa. The Guy has an ex-wife? Someone in his life not thrilled to see him? Angry outbursts?
Ms. Blichfeld said she later heard from fans who were surprised. They told her, “‘It was such a different representation of The Guy. I don’t know how I feel about seeing him break down.’”
Mr. Sinclair said that the realities of being a 35-year-old, low-level weed dealer are catching up with his character. He thinks the show has “earned a little window into his life,” which the new season offers, along with story lines about breakups and changed relationship dynamics that echo the creators’ lives.
‘Me at My Best’
Mr. Sinclair is so naturalistic in his acting that many people assume he is playing a version of himself, or that he is The Guy. Charlie Gruet, a cinematographer on the show since its web days, recalled being on set one day when a bike messenger spotted Mr. Sinclair and yelled, “I’m doing what you’re doing” — though it wasn’t clear if he meant delivering weed.
“Ben has that quality where you just want to hang out with him,” Mr. Gruet said. “The Guy has that similar quality.”
Mr. Sinclair is likewise rough around the edges in his personal grooming, though driving the R.V. he looked stylishly rumpled in a green sweater and millennial-pink pants. And he belongs to the same liberal, diverse, woke milieu as the show’s characters. He attended Oberlin College, claims to have had his life changed at Burning Man and says he is trying to check his power and white privilege.
But where The Guy is a chill cipher who doesn’t say much, Mr. Sinclair is talkative and disclosing, even intensely intimate. Five minutes after meeting, he said that he’s reading a book called “Boundaries and Relationships” because “that’s been an issue in my life.” Then he underscored the point by oversharing that he’s seeing a therapist but trying not to sabotage the process with his authority issues.
“He is me at my best,” Mr. Sinclair said of The Guy, adding that, like the character, “I’m able to achieve a feeling of intimacy with someone quickly. It’s been my blessing and curse.”
Something else he and The Guy have in common: They both own a ’77 Travco.
Mr. Sinclair wound up with the R.V. because he saw a moon lamp made of fiberglass, and then became fascinated by fiberglass as a building material, and then while researching on the web came across the fiberglass-bodied R.V. How The Guy ends up with it on “High Maintenance” is for now a secret, although one assumes the story will also follow a meandering, pot-head logic.
“I was not surprised one bit when he showed me a photo of this R.V. and said he was buying it,” Ms. Blichfeld said. “Ben has a flair for drama. He likes big gestures.”
She added, “Had we been together, I don’t know if that would’ve happened. I’m the one who would have been asking for inspections and things and projecting all the ways the R.V. would complicate our life.”
The motor home, like a fiberglass boat, bobbed and weaved and rocked up the Taconic State Parkway for three hours all the way to Germantown. But Mr. Sinclair looked content behind the wheel. When part of the roof blew off beside a farm on a back road a few miles from the destination, he pulled over, tossed the shards into the back and rolled on. He even arrived at his buddy’s house in time to roll the joint.
In a few days, Mr. Sinclair was scheduled to leave for a monthlong solo trip to Indonesia, to go scuba diving in Bali and Raja Ampat. When he returned, it would be to a new season of his show, a new apartment, a new New York. He was excited about the trip but also nervous, he said, because he doesn’t like to be alone.
He thought out loud: “Is it worth being alone for the sake of being alone because you think you should be alone, or to find solitude just because it’s good for you? Or if you like being around people and that’s just what you like, maybe that’s O.K., too?”
Sounding like one of the endearingly searching New Yorkers who call upon The Guy, Mr. Sinclair said, “I’m trying to answer those questions for myself.”