Ben Sinclair Is Finding His Way

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Ben Sinclair is sitting on a bench in the corner of his neighborhood coffee shop, leaning against a pillow embroidered with the words good vibes. His nails are painted white. The color of his scarf is faded rose. As I put down my bag, he excitedly announces, “They have oat milk here!” while sipping on an oat-milk latte. “I read that oat milk is high femme,” he continues, as we chat about the benefits of various milk alternatives. “I also like hemp milk. Hemp milk is stone butch, or maybe soft butch.”

Fans of Sinclair’s show, High Maintenance, would not be surprised to hear him apply the complicated terminology of a lesbian subculture to milk substitutes. Part of what makes the show so interesting is its fascination with the myriad cultures that make up the intricate social fabric of New York City. In each episode, a pot dealer known only as the Guy (Sinclair) rides his bicycle throughout the city, dropping off deliveries at the homes of a pair of lesbian activists, a novelist with writer’s block, a group of swinging professionals, among many others. A single episode in the upcoming season offers a window into the lives of young people breaking with Hasidic Judaism, arty male burlesque dancers, an ethically challenged Vice reporter, and a pothead Uber driver.

This season is the show’s first with a writers’ room, led by Sinclair and his ex-wife, High Maintenance co-creator Katja Blichfeld, who came out as a lesbian before they started working on season two. In the first season of the show’s HBO incarnation (the project began as a low-budget web series), it was revealed that the character played by Sinclair had been married to a woman who left him for a woman. Sinclair and Blichfeld wrote the episode while they were still together. “It was subconscious, prescient,” Sinclair says, adding, “I think we both knew.”

Critics have happily noted a lightness in tone in season two that had seemed to disappear after the web series moved over to HBO. Emily Nussbaum, an early fan, observed that “a tinge of sourness—or self-loathing, or at least self-consciousness—had harshed the show’s trademark mellow” after it arrived at HBO. Now, she writes, “The ease is back, thank God, and the series feels, even in slighter moments, newly confident, with an increased ability to reflect a larger world in flux.”

Over oat-milk lattes, Sinclair and I discussed what it’s like writing a series with your ex, why he thinks the second season is better than the first, and whether toad venom is the new ayahuasca.

This was the first year you had a writers room, and it wasn’t just you and Katja writing together. Do you feel like working with other writers allowed you to access worlds that you hadn’t experienced personally or wouldn’t have thought to do an episode around?
A little bit. Not as much as I hoped. Writers are in the Hollywood bubble, too. We try to get veterans and nonveterans. At the end of the day, when we asked for writing samples and episode pitches, we read the samples blind because we didn’t want to know who wrote what.

So it wasn’t like you were looking to find writers from a particular demographic or with a specific background.
No, we were trying to do it blind so that we could really just respond to whose writing we liked. That was first and foremost. At the end of the day, I want to be around people who light me up.

I feel like the new season has such a consistent tone, more than the first HBO season.
I agree with that too. Becky Drysdale, who has written on Baskets and on Key and Peele — she’s a comedy veteran and an improv veteran — she is very good at structure and she kept reminding us that this was a whole season with an arc. The arc is in the Guy’s experience. It’s really only visible in episodes 1, 5, 6, and 10. We tried to localize it so that we’d still have modular feeling for the rest of the episodes.

How did you decide to have an arc for the Guy?
Back and forth and back and forth, and I don’t know. Some of the consensus was that this isn’t a show about the Guy, it’s about the other people. But I like how it turned out. It’s an evolution. I think it would be comforting for some for it to just be the same story over and over again. But as a creator — and I think for Katja as well — the evolution is exciting. I think we’re doing the right thing.

I can cop to being a second-guesser. A big thing I learned how to do this year was instead of answering a question right away, I would be like, “I have to think about that. Let me get back to you.” I don’t always have to answer right away.

Would you describe that as personal growth?
I would describe it as a way to manage a habit of impulse.

Critics seem to like season two more than the first season on HBO. How does that fit in with your personal upheaval, and what do you make of that? Was it, in a way, easier for you and Katja to work together after the breakup?
I think part of it was growing pains. I had complete control during the web series days. I learned how to do the one-man band — Katja was there too, of course. But I went from a place of knowing everybody’s name on set to just not having enough time to sit with everyone. I used to cook everyone breakfast when they came to set on the web series. Then when we started shooting the HBO episodes, I remember wanting to take a walk one day and hearing a PA be like, “I’ve got eyes on Ben. He’s on the move.” It was really different. There was a real learning curve.

But, also, Katja and I really weren’t getting along, increasingly. The pressure was increasing, and I was getting recognized when we were walking around Brooklyn. We began to feel like we had something to prove. It was unpleasant.

In the first HBO season, a lot of our stories were about people who were in relationships they didn’t want to be in — even the dog was in a relationship he didn’t want to be in. And in our relationship, there was no separateness. At all. I used to joke that if we were a Venn diagram, it would just be one single circle. And that is really unhealthy.

It seems difficult to maintain.
It’s not only difficult to maintain, it’s uncomfortable. It’s not right. And now that I see the value of separateness and space, I think that’s the reason this new season was better. In that way, it was easier to work together. It had been really hard to feel this pressure with someone at work, and then you go home and want to be there for them, but you also have to self-soothe, and there just wasn’t enough room.

It’s really important to have space and separation.
So important. For instance, I just went scuba diving. Right before we got married, we were in Mexico, and I wanted to go scuba diving, and Katja couldn’t do it. She just didn’t want to to put her head underwater. It was uncomfortable for her. So I was scuba diving underneath her, on the bottom, and she was snorkeling on the top, and I remember really wanting her to be down there with me. It never occurred to me that I could just go scuba diving by myself. We were together a total of eight years — and I stopped scuba diving. I should’ve just gone scuba diving.

That’s a good metaphor. 
Yeah. I could’ve just done that, gone deep. But I spent a lot of time focusing on her — looking at her facial expressions as a sign of how I should react to things, and not really getting a good sense of how I felt about anything. The space to decide what I think about things has made me happier, and I know it has made her happier.

Do you feel like that space is what allowed you to go deeper into the Guy’s storyline?
I can go in deep and say that at the end of last season, when the Guy goes into his ex-wife’s girlfriend’s apartment down the hall, there had been no talk of us splitting before that. None of that was ever discussed.

Where did the idea for the episode come from?
Katja was supposed to go to Berlin, and I had planned a trip to go to California. Then she ended up canceling her trip to Berlin and I still went to California. I think she enjoyed that I wasn’t around. I don’t want to make any suppositions, but I suspect that her interest was in showing a character that wasn’t excited to see the Guy. And then I came back from California, and I put in the idea that this character was the Guy’s ex-wife’s lover.

Do you think this idea that she was going to leave you for a woman was haunting you both in some way?
I can’t say consciously that I knew any of that. But what I like about that episode, in general, is that it takes a person — the Guy — who you think is very happy and calm and collected, and it reveals about him that he’s just like everyone else: He gets frustrated, he gets scared, he gets angry. That felt like a twist. And in a way, that felt cathartic.

Do you think that you subconsciously knew you were soon going to split up?
I think we both knew. But nothing is slower than a fizzling-out relationship. It was building over a couple of years. I would say around the time of the Vimeo season — that was when all of the attention started focusing on me and that’s when it started to feel like, oh man. Before that, it was like, “We could work through all this stuff.”

How did that pressure and the fame affect the relationship?
I became a little paranoid about making sure that any positive attention that was directed toward me got split up between us both, and I became very vigilant about it. If anyone who wrote about the show, if they just included my name or something, I would write the writer a note and say, “Hey, it’s actually a show by two people.” I became demure — like if we were on the subway together and someone came up to me and said “Great show,” I would become a little bit nervous. I’d be like, “Look at Katja, she’s also a creator too.” I was nervous, because I didn’t want her to feel bad. And I also didn’t want me to feel bad, hearing her feel bad. I made a lot of clumsy efforts in order to graciously deflect the attention onto both of us, instead of just me. And that made the expectation of getting noticed and positive attention not feel good to me. Which brought up a lot of complicated feelings because this is something I have wanted a lot. It made me felt like I couldn’t enjoy the success that I had worked for. And sometimes I resented that.

It was a very double-edged-sword situation. I had everything I wanted, but I was struggling to enjoy that because it felt painful. Because I had something so many people wanted, and yet I couldn’t find any happiness.

I think that’s an experience a lot of people have with fame. It’s so often not what you hope it will be.
Well, what did Oscar Wilde say? “There are only two tragedies in life: One is to get what one wants, and the other is to not get it.”

But the lucky thing is that the rise of the show has been gradual. If it was some kind of catapult, overnight thing, I think it would’ve been really tough to deal with. Also, I’ve had really great support. I really, really value that. And that’s why I’m pretty excited to do this again. That support is already in place, and I think that the people in that safety net still want to be there. Not just for me, but for this whole family we’ve created.

I think it’s interesting that in season two, the Guy is starting to have professional frustration that we hadn’t really seen him have before.
Yeah, he’s 33 years old and selling pot. Later in the season, someone from college bumps into him, and you see a little bit of embarrassment about that.

He’s selling pot, but he’s not part of the new pot.
He’s nostalgic. When his ex-wife goes into his apartment, it’s nostalgic. It’s got like afghans and a Nintendo system and a vinyl record player. I don’t know if we were trying to depict him as resisting change or something like that, but that’s just how it ended up.

Do you see him, in a few years, become some sort of pot entrepreneur, being part of “the Green Rush?” Can you see him making that transition?
I can see him being tempted to do so. His interest is in people. His interest extends beyond getting stoned. I think this is a step of his life. I remember early drafts of season two, episode one, the Guy is having a vivid dream because he had stopped smoking pot, because he wanted to take a break. We ended up cutting it, but I was interested in that because I was also taking a break myself.

What inspired that break for you?
I do it every January. I know that for the past ten years, I’ve smoked too much. I know that I’ve used it as a way to hide from discomfort. I also have kind of a good-boy complex. I’m the youngest of four. My mother used to be the cantor of our synagogue, and she was also a music teacher out of our home. So there were other people’s kids in our home all the time. And my dad was a teacher, so he had a whole class of other kids. I was really fighting for attention, and my parents really didn’t have a lot of energy to put towards me at that point; they were working really hard. So, I was a troublemaker. Whatever attention I could get, positive or negative, was what I wanted. When I smoke a lot of pot, I’m wondering if this is a bad thing that I do. It seems like I’m shucking some responsibility. Then there will be times in my life when I’m like, “Dude, you’re doing okay.” But my family is overachievers, and I come from a culture that’s like, you can always do a little bit better.

So that fuels the need to take a break?
I need to be able to show myself that I’m not addicted. This year I feel less addicted. Not to say that there isn’t some sort of muscle memory of getting inside this apartment where I live and, you know, smoking at the end of the day. But I have no problem whatsoever with not smoking. It’s one of the reasons I like pot, because it lets you let go of it. There’s not an intense withdrawal. There is a withdrawal, though. The dreams are probably the most uncomfortable.

I could imagine that when you and Katja were still together and not getting along, smoking would become an important way to decompress together.
It was a very important ritual. Extraordinarily important. And especially for her. The pieces that are written about her in Vogue and in the Cut describe a very uncomfortable person holding onto her own shame. There’s an article where she talks about this moment where she had trouble getting out of bed when we were together, and I had to call a therapist for her. I was very scared. She couldn’t describe really what was wrong with her, and I remember being very concerned for my friend.

I’m so glad for her — I really mean it. It brings me so much joy to see her so alive right now. All I ever wanted for her was to help her. When I stopped needing to be the person who helped her find that lightness, it really freed both of us up in so many different ways. And it freed me up to pay attention to helping myself with what I needed. Just as much as smoking pot was a diversion from dealing with my issues, so was trying to help her with her issues. I’m on my third therapist in five years. The first two were men, who I found ways to disqualify as being helpful to me. I’ve been with my third therapist for a year and a half now, and I really believe that she’s there for me. I get it now — that if I choose to not accept help, I’m the only one who’s losing out. The therapist still gets paid and their schedule is filled. So it’s been awesome to put on my own oxygen mask for once.

What was it like having the writers room there as you were both going through this breakup?
The first day we were like, “Hey guys, here’s the situation. We’re splitting up. This is a very strange situation. And we’re going to be super open about it. And this is not necessarily a demand that you be as open as we are, but we’re just letting you know that this is what’s going on in our lives and we hope that this room can be a safe space for us to say what we need to say and breathe. If it helps you to say what you need to say about your personal lives, that opportunity is open here, but there’s no pressure.” Some writers took us up on that more than others.

It’s cool to have an opportunity to creatively express all the crazy shit you’re going through.
It’s very luxurious. Although sometimes — I don’t want to speak for the others — but I know that I would go home thinking about what we said in that room. It felt like group therapy sometimes. Sometimes it was just too much. Sometimes I was like, “What did we do? This is a lot of weight.”

Do you feel at all conflicted about doing another season?
Not all. I think it would be awesome. I really think that High Maintenance is still jammin’. I could jam on it for a couple of years, and I don’t want to get too distracted from it. But I also want to put my eggs in another basket.

What would your dream next year consist of?
I have other things I want to do. Katja has other things she wants to do. It would probably be pretty cool to put our eggs in another basket, and I have shows that I’m excited to develop and am already talking about developing shows and features. I’ve been writing a lot lately. I like using my brain and my observational skills. A few weeks ago, I went scuba diving and took a little bit of mushrooms while I was scuba diving — just a little bit — and then a movie came to me underwater that I think I could write. I’d like to direct other people’s’ writing. I think it would be fun to work as an actor with a director who I trust in completely.

I work best when I’m taking a walk or taking a shower. I didn’t like the writers room in that we were sitting in the same office during work hours, ten to six, eating carbohydrates and saying, “Goodnight everybody, see you tomorrow.” My ideal would be putting a bunch of writers on a train and going from L.A. to New York for three days and then coming back — or going on a walk or going to a museum together. Or just being out in the city that we’re writing about rather than sitting in a traditional office building.

Do you feel like, in general, you went from a period of feeling sort of stuck to feeling like you are moving and exploring again?
Maybe so. I felt a lot of shame. I wasn’t appreciating fully all the good things, and I think that created a certain amount of self-contempt and discomfort. And I think I knew for a while that things weren’t going well romantically and that felt shameful. Shame is not useful. And the only way to get rid of shame is that — it wants to hide, so you have to put light on it.

I really was afraid to tell my family about the divorce. My parents got together when they were 12 and have been together since they were 12. I’m the youngest of four siblings, and each one of my siblings met their spouse when they were in college. I’m the only person in my family who’s dated post-college. So we never really had a concept of divorce in my family, at least not in my immediate family. And I was really ashamed to tell them about it. It didn’t feel comfortable. And I think even to this day I don’t quite know how to necessarily go to them for comfort regarding this.

But you’re doing some things right.
Something’s happening. I think I’m doing a lot of things right — which is really to say that I’m doing the best I can.

So what do you do to decompress and reboot creatively?
I go on trips. I dance. I go to this party called “The Get Down.” I go on dates. I have a group of friends that I’ve known since I was in high school who live in New York, and I see them sometimes. I’m pretty good at keeping in touch. I’m a very social person. I try to read a mixture of introspective, self-help-y books. In 2017, I did quite a bit of ayahuasca. But I was mostly doing it because I thought I wanted to do an episode of it. So I didn’t end up having any profound experiences because I was trying to watch everything and everyone. It was not a pure motivation. It stopped me from going into the place that people can get to. The show makes me want to suck up everything, soak up all of the details. I tried to make an episode about it for a while — but by then, I realized, “You know what, this is boring. This is passé at this point. It’s old.”

It does feel very 2016.
Yeah — which is when I started with it.

What’s the new thing?
People are doing toad venom now. In the drug world it’s called kombo. I don’t know. Maybe oat milk is the new ayahuasca.

What I’ve noticed most about ayahuasca — and whatever the new ayahuasca is — is that my generation and the generation before, we want instant results, and I think that is always the stumbling block. The impatience with process. The folly is thinking you can change overnight.

This interview has been lightly edited and condensed for clarity.

Ben Sinclair on Writing High Maintenance Through a Breakup