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Inside the ups and downs of High Maintenance, one of the best NYC shows ever

HBO’s underdog High Maintenance returns to hold up a (smoke-filled) mirror to Brooklynites—and the show’s creators

Written by
Jillian Anthony

It’s said that art imitates life, and for Brooklyn-set High Maintenance creators Katja Blichfeld and Ben Sinclair, that’s a gross understatement. Take the first episode of season two of the duo’s HBO show, which opens with the Guy, Sinclair’s weed-dealing everydude, receiving a phone alert that “something bad happened.” Viewers quickly understand (though it’s never explicitly said) that it’s November 9, 2016, when the city awoke to the presidential election results and seemed stuck in a fog of disbelief. The draw of High Maintenance is that—in a sea of series that claim to depict the “real” New York—it conjures up an awed feeling of déjà vu for locals, even when plotlines delve into the absurd. You leave scenes thinking, That’s my city. That’s my life.

But the low-budget gem, which started as a web series in 2012 before making the leap to HBO in 2016, reflects reality even more sharply for Blichfeld and Sinclair: The pair had been married but split up on election night, and Blichfeld later came out as gay. (She Instagrammed a photo of herself overlaid with the words GAY AF on National Coming Out Day.) From their breakup through July, “it was probably 70 hours a week together,” says Sinclair. “Our relationship and the phases it’s gone through in the last year is very much represented in the show,” adds Blichfeld.

Last season’s cliff-hanger revealed that the Guy, whose personal life was previously a mystery, lives down the hall from his ex-wife, who in turn lives with her girlfriend. And it gets even more bizarre. Blichfeld, a platinum blond who exudes an enviable self-confidence, had a bad bike accident last fall that sent her to NYU Langone Hospital and left her with facial scars for weeks. Guess what? A few months earlier, Sinclair acted out his own fictional scene of an ex-spouse visiting the hospital, when the Guy crashes his bike and his ex-wife brings him clothes and comfort. “I had to work through some shit via this show, and I was grateful for that,” says Sinclair, rocking the unruly beard and sense of wide-open wonder akin to his insatiably curious character.

With coffees in hand at a picnic-style table at Berg’n, a beer and food hall in Crown Heights that’s in the same building as their office, the still-close collaborators (oh yes, they live within walking distance of each other) sat side by side and shared insights on their new season and new lives—together and apart.

How do you feel about season two?
Ben Sinclair: It took us about a year to do it. We keep doing twice as many episodes as we did the year before. This is 21 short stories. Originally an episode was one short story, but now an episode is two or three?
Katja Blichfeld: Sometimes four.
BS: It’s kind of like making a pilot every time. You have to introduce a new character with a new location and a new soundtrack and a new style and tone, so it’s a lot of work. It would be kind of luxurious to have just one character that you show through the entire season. What would it be like if you went to work at a set apartment?
KB: We really have no character where you’re returning to their home. So it’s a lot of locations.
BS: Or it’s like a year or two later.
KB: Right, and sometimes we don’t have access to that apartment anymore. And we’re like, I guess they moved. Write it in, you know? So we did, because we do have a lot of people returning from the web series this time around.

The Guy, especially, gets more of a storyline this time.
BS: One of the criticisms but also strengths [of the show] is people wanted to know more about the Guy, so we decided it might be interesting to scratch that itch this year.
KB: The first episodes we released were in 2012, so here we are in 2018. It seems like it would be a little strange to not give you a bit more information on him at this point.
BS: If we ever get the chance to do more episodes of High Maintenance, next year, weed could be recreationally legal in Massachusetts, which is right there, and Maine and California. We need to have some sort of background for that for future story opportunities. You need to have context for the vendor.

Do you think weed will be legalized in New York?
KB: I think it would only be positive if it happened, just to have the decriminalization aspect. It’s just ridiculous that it’s even a thing.
BS: Well, everything’s ridiculous. Every day is like, Whoooa.

Speaking of which, what was it like crafting the first episode of season two?
BS: The day that episode got seriously discussed was Inauguration Day. [In the writers’ room] we were like, I’m sorry guys, we can’t just keep talking about these other stories like this isn’t happening. We’ve always wanted to have people who watch our work feel recognition, like, Oh that’s the New York I know, or that’s the Brooklyn I know. And right now the Brooklyn I know is a lot of people smacking their foreheads with the palms of their hands and being like, What the fuck is going on?
KB: [The election] caused a lot of people to question their belief system, their value system and their way of life. It just felt impossible to ignore. I remember how Sex and the City never addressed September 11. [On November 9] there was a sense of connectivity among strangers. I realize there are people who felt differently about those results in this city, but in our little Brooklyn bubble it felt like a real tragedy.

Similarly, on the show, the characters are connected but often so lonely.
BS: In the past we would say loneliness was the constant theme throughout our work.
KB: It’s such a weird thing that one can experience loneliness in this city of so many, and that loneliness is amplified sometimes because if one looks outside the window there’s so many people out there, whereas if you were just out on a rural plain or something then it’s probably experienced really differently. It feels like it’s not a choice here to be alone, but it kind of is because once you go into a public space, you’re surrounded by people. It’s very hard to find physical solitude here.
BS: And survival can be a very lone pursuit, especially if you’re a workoholic or an ambitious person. I’ll classify myself as a workoholic.
KB: Me too. The loneliest person in season two is The Guy, and a huge part of his arc is him dealing with his loneliness and his workoholicism and navigating that.

“Right now the Brooklyn I know is a lot of people smacking their foreheads with the palms of their hands and being like, What the fuck is going on?” -Sinclair

It can be cringeworthy to watch these people talk onscreen, maybe because I see myself in it.
KB: Looking in the mirror isn’t always that cute.
BS: We’ll make different cuts of our episodes, and we analyze the feeling that you have when you walk away. Sometimes there’s a cut with a good feeling attached to the end of it; sometimes there’s a less good but warm, contemplative feeling that stays with you longer. Then you find yourself thinking, Why did I feel that way? And I think we usually opt for the contemplative, kind of messy, kind of what the fuck was that? feeling.
KB: I have a real aversion to an ending that’s too neat and tidy. Life isn’t like that.

Are both of you as naturally curious as the Guy?
KB: I do feel Katja 2.0 is a lot more—I’ll talk to strangers but I’m also observing in the corner secretly.
BS: You think 2.0? I think it’s more 4.0 or 6.0.
KB: I’ve had a lot of lives, it’s true. But this current iteration of my life, I feel like there’s a lot less to lose and I feel like—probably since coming out and the election—I do feel more personally empowered to interact with strangers and make connections with people that i may not have previously made connections with, just because I have this urgency about life now. Time is passing and I don’t wanna have regrets. So I’m a little more apt to engage with life in this way that I didn’t since I was, like, in my twenties and a little more fresh out of the suburbs in the big city. Ben, you can speak for yourself, but as a person who was with him for a long time, he has always been very good at being open to random encounters.
BS: I would say only in the past like four, seven months I’ve been starting to figure out how to back off a little bit and claim some space for my own, because it’s a matter of self-respect how much space you give yourself. And I have been known to give everything to other people and that might not always be safe. I hope at the end of this season there is a feeling of, You can think of it as loneliness or you can think of it as solitude. I’m trying to get more toward celebrating solitude rather than fearing loneliness.
KB: We’re sort of both taking a weird turn from past selves. I feel you’re turning more inward and I’m turning more outward, like revolving doors.

There’s also a storyline about the Guy’s ex-wife struggling with pot use and dissecting that. And you have talked before about feeling that yourselves.
KB: That character is the place where we put that exploration.
BS: You said at a talk once—and I thought it was very smart—“Is this time right now a good time to be fucked up? Is this an appropriate time to—
KB:—check out?” It seems like sobriety is almost imperative more often than not right now. If you can stand it. [Laughs]
BS: Should we sit with those feelings and work through them instead of just numbing them and checking out? It was definitely on our brains this year, and the Guy is feeling unrest about being alone—and I think at the end of this season we do give him a choice to either enjoy his life or feel those seeds.

The show closely mirrors your personal life, and your personal relationship changed this year. How is that expressed?
BS: I think the hospital episode [in which the Guy is visited by his ex-wife] was the first one we shot. I thought it was an ideal of how we would treat one another in the future as friends. When we were filming the last episode, Katja got into a bike accident, and the irony of that is not lost on me at all. We were able to portray something and then follow up on that by acting it out accordingly.
KB: I don’t know other people that had their lives as enmeshed as the two of us, then break up and have to continue to work together because of a contractual obligation. [Laughs] So the fact that we did, and we’re still sitting here laughing and joking, and we’re fine by all accounts-—I’m really glad that’s how things have shaken out. It was exposure therapy. Our divorce mediator says we might be the easiest clients she’s ever had.
BS: I would love if anybody [who’s] going through any symbol of struggle in their life with their partner could see by example that you will be okay at the other end. You don’t have to blow your whole life up. You just have to make choices that are healthy for you, and if you love someone, you have to be happy for them doing whatever makes them happy, despite how you feel.
KB: This show forced us to confront a lot of things personally and to deal with them in a mature way, in a proactive way. If we did not share this show, who knows how things would have gone down?
BS: Maybe more traditionally.
KB: Which is to say more negatively. Who can say? But I do think that High Maintenance—in an interesting, weird way—preserved our relationship to some extent and that’s cool.

The season two premiere of High Maintenance airs January 19 on HBO.

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