How High Maintenance season 2 saved its creators from themselves

For Ben Sinclair and Katja Blichfeld, co-creators of the anthology series High Maintenance, making season 2 was a joint(sorry) effort with quite a catch: Sinclair and Blichfeld decided to separate and pursue a divorce before writing the second season.

That meant making some changes to how they write the stories that make up their thoughtful, inventive anthology series. They gained a writers’ room for the first time and handed over directing duties to, well, other directors, all while working side-by-side on crafting and filming the new season.

But High Maintenance was built to adapt. The show began as a web series on Vimeo in 2012, telling short stories about the customers of a weed dealer known only as The Guy (Sinclair), before being picked up by HBO in 2016 and subsequently launching a season on the premium network. And though making the leap to TV added some constraints thanks to airtime, Sinclair and Blichfeld used the opportunity to toy with framing (think the episode titled “Grandpa,” told through the eyes of a dog) and expand the stories of some characters they’d previously spotlighted on the web series.

In season 2, the character who gets expanded the most is the Guy himself. Sure, the season’s packed with vignettes about New Yorkers/Brooklyn-ites/out-of-town-AirBNBers, but this time, life off-camera, both personally and politically, bleeds into the new batch of episodes. Critics have noticed High Maintenance‘s new vibe: The New Yorker pointed out the second season’s “willingness to dwell on more uncomfortable aspects of its subject matter,” while The Cut praised a “better, richer version of the show” thanks to episodes centering around “escape, with all its attendant thrills and responsibilities.”

So what can viewers expect from these new episodes? The premiere follows the Guy on a grim day in the city, when a disaster of some sort has shaken New Yorkers anew. The second episode chronicles a married couple visiting their daughter before pivoting to a women’s group gathering for poster-making and wine-fueled discussions about the state of the feminist movement. And then there’s an episode that delves into the Guy’s life — one that oddly mirrors Sinclair and Blichfeld’s own story.

The pair spoke with EW in December, while working on post-production for the season. Below, they delve into how their personal ups and downs affected their creative offspring, the evolution of High Maintenance over the season, and what they hope fans take away from their newest — and perhaps most moving — season yet.

ENTERTAINMENT WEEKLY: This year, the first episode tackles the post-election mood without ever mentioning the election; it’s just clear that something happened that’s got everyone in New York feeling down. How much of this season dives into that feeling?
KATJA BLICHFELD: Definitely the first couple feel sort of reactionary to [the election]. We talked a lot about how things feel very pre-election and post-election, and I don’t think we were necessarily wanting to write anything particularly political, but we also couldn’t ignore how this is a different time, people are feeling differently than they did a year ago. There’s a different energy out there. There’s a different quality to the conversations we’re having with our friends and family.

BEN SINCLAIR: You know, when we first started the season in the wake of the election, I was really hoping that this series would be an antidote for the feelings of negativity out there, but as I matured over the year in my own personal goals, I realized that the only way to get through something is to go through it. … I think that we went through difficult feelings post-election and post-marriage, and we have kind of a moody season as a result, but I think it’s helpful to others to know that other people are going through something just as you are going through something. I think we collectively are going through some painful realities together. And I hope, in a way, that is the antidote I’m looking for.

It’s interesting you mention this season being moody, because to me it just felt… bigger. The Guy’s life — the whole mythology around the Guy — gets explored much more this season. What was the drive behind doing so?
SINCLAIR: It just ended up that way at the end of last season. Katja wrote the outline for the very last story, which was the Guy getting locked out of his apartment and going down the hall to his ex-wife’s new girlfriend’s space and waiting to get in. Katja started that story, we finished it together, and then it kind of just ended up happening in real life. [Blichfeld laughs.]

We separated on Election Day, and then while making the season, we just kind of dealt with that while we were trying to keep working together and living down the street from one another. I mean, it felt very serendipitous and spooky all the time, as we would be mourning the way our life used to be together while the rest of the country was mourning the way life used to be. We could kind of hide our sorrow in the collective sorrow, but still we had to make this project together.

It was a real back-and-forth because I had a temptation to live out my pain through my character, and everyone told me not to. Not everyone, but there was a lot of, like, “No, this show is not about the Guy.” And so we and a lot of our writers’ room and our producers wrestled with how much to put in.

BLICHFELD: Yeah, it’s tricky because we went from nothing to a lot, right? I think that was a delicate balance we were always going to be navigating and negotiating. I also believe that ending up with the Guy having an actual arc over the course of the season is a direct result of having a writers’ room [this year] full of seasoned writers who are oriented toward creating a television show, whereas Ben and I are more short-story-oriented.

SINCLAIR: A part of me was like, “Oh, I just wish I told seven-minute short stories forever, and we never delved into his life,” and I’m sure some audience members would like it if we just kept on doing what we’d been doing, but I want our show to evolve.

BLICHFELD: It would have to!

SINCLAIR: I think it would be a shame if we just were one-trick ponies, like some sort of formulaic Two and Half Men sitcom. Like [laughs] I mean, I don’t know. I’ve never seen Two and a Half Men, so… I think that we’ve stayed away from the Guy long enough to earn a little bit of time with him.

BLICHFELD: And we’ve also set ourselves up as a show that does change things up all the time, so it didn’t feel weird to break course.

Let’s talk more about how meta this season becomes. What was the biggest challenge to having the Guy’s story reflect your own? Did it make it even harder to work on the show together?
SINCLAIR: It was a very hard year. It was extremely difficult. I think that what Katja and I did in the midst of working together so closely post-separation and on into our divorce was an unexpected kind of exposure therapy in which we were able to watch each other go through painful moments and moments of relief. Watching her move on with her new girlfriend was hard for me at first, but now I’m quite happy for them in a way that makes me feel really good, because it’s like a true kind of love where you want the person that you love to just be happy, whether you’re involved or not. And for me to kind of get to that place while working 50 or 60 hours a week next to her —

BLICHFELD: But you had a love life too!

SINCLAIR: I had a love life too, it’s true. Sometimes we had our significant others on set and they were always very graceful about it, and it was really an opportunity for everyone to step up and to show how graceful they could be in a very strange environment.

BLICHFELD: It was strange.

SINCLAIR: It’s only secured my faith in the structure and community that I have around me, that I’m just surrounded by wonderful people who can really roll with anything in such a respectful and lovely way.

BLICHFELD: I think the show and working on the show through these circumstances really kept us accountable to our higher selves, you know what I mean? Like, there were a lot of days where it was great and easy and like, “Wow, nothing’s really changed,” but then a lot of the time there was a sense of, like, pain because of memories or baggage or triggers [laughs] or what have you, and I think, had we not had this show and this contractual obligation to complete it, we may have fallen victim to childish emotions or childish behaviors. So really, in a cool way, I think at the end of the day it sort of pushed us to be our best selves.

SINCLAIR: I think sometimes when people break up and they’re absent from each other’s lives, there are all sorts of these mental machinations that happen afterward, where they’re wondering if they’re happy or what they’re doing, or “oh they’re probably happier than I am.” We didn’t have to do any of that.

BLICHFELD: Yeah, it was all in our face.

Before we wrap up, I want to know a little more about the future of the show. If you could have another season, how would you like this show to evolve? How would it work?
SINCLAIR: You know, I think we have an excellent boat, and over the years we built a boat with a great crew. So why the f— would we get off the boat right when the captains have decided they should be co-captains? All we have to be good at is keep steering the course and give each other a break and trust each other to be captain when it’s our turn to be captain. The boat — there’s nothing wrong with the boat. We just needed separate living quarters on the boat.

BLICHFELD: I think, too, this last season was a cool exercise in bringing other people to the table to collaborate in a more meaningful way. We had other directors — like Shaka King and Eliza Hittman, who were directors we respected a lot before this and even more now — and the writers’ room. Those were two very new dynamics for us, and they went very well, and I think it’s going to be interesting to see what happens when we get another season, now that we have invited other collaborators. We won’t necessarily be a directing team anymore, but that will be the new development, I guess, for next time.

SINCLAIR: It’s funny, some of the people at HBO were very tiptoe-y around us regarding our split, and I wish somebody would have said, “Congratulations on getting what you wanted!” I think, like, it’s really, it’s not bad at all. I just wish that when we’re covered for this season, people aren’t tiptoeing, like [lowers his voice] “Oh wow, they couldn’t figure it out.” No. Like, we are figuring it out.

In the end, then, what do you hope people take away from this season? You may have figured it out, but it does feel… changed.
SINCLAIR: Yeah. [Pauses] I don’t know if the season says it as much as I want it to, but I just wish people would choose love. I think the way the Guy interacts with some people this [season], he doesn’t seem to take anything personally. He doesn’t hold a grudge against feeling like things aren’t working out the way he wants them to. He chooses love in the end, I think.

[Turns to Blichfeld] Like one day when we were filming in September, Katja got into a bike accident on the way to set, and I was biking to set, and I got a call from her, and she says, “Ben, I’m f—ed up, I’m really hurt.” And then I sped over there as fast as I could, and I got to where she was sitting on the road bleeding, and there were people with her, and I went, “I’m her husband, let me help her out.” It was just, it was crazy. For a moment there, I was like, “Oh, nothing’s broken. What we created together is there always.” It’s because it’s been created, and if you just choose love instead of feeling hurt, everything’s going to be okay.

BLICHFELD: Yeah. And I would just say, what I wish for people to take away is a reminder that change is inevitable. We can count on so few things, but we can all count on the fact that change is going to happen in big and small ways all the time, and it’s going to be okay. Even when it feels painful, ultimately it’s okay, and it’s one of those realities of life and, you know… [laughs] It’s okay! I just want people to feel like things are going to be okay.

Oh man. This might be the first interview I’ve ever done where at the end I want to cry.
SINCLAIR: I almost did! I almost did. But then my manhood helped me.

BLICHFELD: [Laughs] I do think [turns to Sinclair] what you said about choosing love, you know, I think our finale episode is a manifestation of the “change is inevitable” and “choosing love” sentiments. Those things are very expressed in the last one.

High Maintenance returns Friday, Jan. 19, at 11 p.m. ET on HBO.