In Pretty Problems (2022), which will premiere at SXSW on March 14, couple Jack (Michael Tennant) and Lindsey (Britt Rentschler) confront their flagging relationship while on a weekend retreat at their new friend’s gauche vineyard. Suddenly thrown into the realm of the super-rich courtesy of Cat (J.J. Nolan) and her husband Matt (Graham Outerbridge), Jack and Lindsey have to navigate uncomfortable discoveries about what each of them wants out of life. Joined by absurd couple Carrie (Charlotte Ubben) and Kerry (Alex Klein), the weekend pushes everyone to the limits of how they see themselves.
In addition to co-starring in the film, Tennant and Rentschler are longtime friends who co-wrote the script. I had the chance to sit down with the two of them. We chatted about their creative processes, friendship, and how they hope to help people laugh during bleak times. The following is that conversation, edited lightly for length and clarity.
Devin: From my understanding, the two of you wrote this movie together. I want to hear about the collaboration that went into synthesizing this idea and writing the script for Pretty Problems.
Michael: I’ve been having a lot of like ego moments around this about the story by thing. But, this just doesn’t happen without Brittany. Like, she just was my muse. She was my inspiration. I’m more Klay Thompson in the corner, just passing the ball hit three-pointers. Take it, Britt.
Britt: So Michael and I have been friends for 10 years. We met in an acting class and became very fast friends. We really love to work together, and over the years have developed a great relationship. One day he called me and he said “Listen, I’m really nervous about this but fuck it I just read Brené Brown’s Daring Greatly for the second time and I’m feeling really fired up right now. So I wrote this script. I have 10 pages written Will you please read it? Be gentle” So I took it to a coffee shop. And I, you know, with that kind of setup, I was like, oh my God, that’s so sweet. What is this gonna be? I read it, walked out of the coffee shop, and called him immediately. I was like, Michael, we have to make this. This is so great.
It was so arresting. I went over to his house immediately. We sat in his backyard, we cracked open a bottle of wine. We chatted and I was like, tell me what you what you’re thinking. He says, “I want this to be a weekend. I want it to be wild. Here are the themes that I’m working with. You reach these ceilings in relationships, you want more you don’t know what to do about it. I want to use this mentality of escapism and vacation talk.” We got down to it and did an itinerary for the whole weekend by thinking of the weirdest, wildest, craziest things we could imagine them going through.
Over time we just kept moving the needle on like, this is how I feel in a relationship. When I’m in a fight with my partner. This is something I’ve wanted, this is something I’ve fought for. This is something I think is so unfair, you know, and hopefully, throughout the movie, people side with different characters. Sometimes you’re like Jack’s got it. And sometimes you’re like, oh, man, come on. That was really the relationship from inception to the delivered product where Michael is just cranking out pages and being so open to exploring things. He let me get my hands on the female dialogue. We worked on jokes and the whole thing was really collaborative.
And then we hit a pandemic. We were about to shoot two weeks before the pandemic locked us down. So while we waited, we just kept open Google Documents and late-night text threads and kept working and working and working. And that’s how it was born.
Devin: That’s such a lovely story! Thank you for sharing. I want to stick with your friendship for a minute. Now knowing that you’ve been friends for so long, I’m curious how that impacted your performances as an unhappy couple. Did your closeness and shared history make playing a couple with so much baggage easier from both a writing and acting standpoint?
Michael: One-hundred percent. And, actually, may I curse Devin?
Devin: [laughter] Go nuts.
Michael: [laughter] Fucking fabulous. So I used to run this bar in Hollywood as my side gig. I was doing the occasionally-booking-work actor thing. The first time I met Brittany was at her old apartment in Beachwood, and we had rehearsal at 12:30. I showed up and I’d been up until like, four o’clock the morning. I was a little hungover, and I was the first person to show up to the rehearsal. I’m like, I’m a little fucking hungover. And she was like, “Well, I’ve got coffee and bourbon and no one else is here yet.” Immediately perfect. We’ve been friends since our 20s. We watched one another go through some really shitty relationships in our 20s. We were both at each other’s weddings. We’ve just always had a deep connection.
So, when I had this idea I brought it to Britt like she said because the way I’ve always seen it is that it’s her, and it’s me. [to Britt] It’s always you and me. There’s no one else around I want to work with as much. And I was at this point where I realized no one is handing me the life I want. I kept asking agents, producers, and other industry people to hand me the life and the career I wanted, and I just kind of realized that I had to do it with my people if I want to really tell stories. I started working on this outline, and my ex and I were having this conversation around “Let’s do the indie thing that we always do.” Let’s like stunt cast, TV actors that are kind of recognizable that are on hiatus.
But, then were at dinner for my birthday, in the before times, and I was looking around the table at Britt, her husband Graham [Outerbridge], our friend Clayton [Froning], and everyone else and had a thought. What if we just go make this with our friends? Like, what if we just go make this with our family? What if we just make this with people who will show up for one another, and who will really trust one another and care for one another? It probably helped that we had gotten very drunk and Britt gave me a spliff with a little tobacco in it so I ended up being up all night thinking through it. But yeah, when I woke up the next morning I called her because she’s my favorite actor on the planet and we really got to work. I’m rambling because I love it so much.
Britt: I’ll pick up the ball, boo. To answer your question, it was easier because we already cared so much about each other, and we know that we cared about the project. We’ve both been through careers where we get told no almost all the time because someone is a bigger name. Because you haven’t done enough yet. Whatever reason the door is getting shut in your face. We see each other every week for class and we go through these things together. And to have a moment where we could all meet and say no, we’re going to say yes. We’re all saying yes together and we’re going to open this door for ourselves, and more importantly, bring each other along.
Devin: Happy to say that, at least for this viewer, that closeness shone through in the finished product. Turning now more to the content and what we see acted out on screen, Pretty Problems has a wonderful zaniness to the comedy, a proper sense of play. How did you all approach creating that tone as a cast?
Britt: Well we were super lucky to have Kestrin [Pantera] agree to direct because she understood the script right away. She got the mix of drama and comedy. In terms of that sense of play you mentioned, she did this amazing thing where she made sure we got at least one useable take that was very grounded and stuck to the script. Once she knew that we had a basic version for the edit she opened up the door and let everybody touch the ball. Improv all over the place. And again, we had a sense of trust with each other that no one was going to take the ball and run for the sake of running. Everything that everybody did was in service to the script and the story, which is why we could let everybody go.
A lot of the wilder moments, I think Michael has said, are probably 70% what was written and 30% of our wonderful friends with genius moments coming through. And yeah, Kestrin would have to come in every now and then and be like, Ah, can we have it just a little more civilized. Let’s take it out of American Pie just for a second.” But because of that, and because of our amazing editors, I think we got to mix in the more grounded moments with the madcap ones. In essence, we didn’t have to run it through five different people to get approval at the moment. We could make a decision, and then the moment would work so well, because of that freedom.
Michael: I spent a lot of time the last five years producing movies, and I got really depressed because I kept watching people make movies for the wrong reasons. People wanting to eat sushi, wanting to drink wine, drive German cars, and tell their friends that they stood next to a celebrity on set. It just made me really depressed. Then getting to do this with this group of people brought me out of it.
Devin: Nothing better than messing around with great friends at a vineyard to cure some creative blues. Speaking of which, one of the highlights of the way you both, alongside Kestrin, structured the vineyard section of the film. Once Jack and Lindsey end up there with Cat and her friends, characters pair off so we get to see all these personalities play up against their expectations and reservations about one another. Was that an intentional move to try and show off every facet of these people?
Michael: Yes. Short answer. Yes.
Britt: Yes, and the long answer is, we wanted to explore a lot of complicated themes with this. But ultimately, we wanted to deliver it as a comedy. You know, so if you’re thinking about those things, about the expectations, about the dynamics, about the wealth gap, about all of these much bigger conversations, then we did it right. We’ve seen this movie before where everyone’s one-dimensional. We’ve seen it, you know. It’s not interesting if everybody only has one particular idea banner that they’re waving. And so Michael was very careful as he explored who said what and when, with whom, so that we could explore these different sides of people.
Michael: I actually think Carrie and Kerry are the most honest characters in the entire movie. Because they just…that’s just what they’re doing. I really just didn’t want to paint the rich people as just assholes. I knew I wanted them to come off as assholes, but then also give them three dimensions. They’re people too and they’re dealing with their own shit. They’re just dealing with it in a way that they can jump on a private jet or buy out a concert. My favorite scene in the movie is Graham and me in the pool. Graham delivers an unreal monologue about finding yourself. He’s so grounded. And, that character could have come off as such an asshole but he did such a wonderful job of making him so three-dimensional. The amount of play that was on set gave us all so much grace to work with.
Devin: Well, lemme tell you. When you can have an existential conversation in a pool and there’s a unicorn floating in the background? You’ve definitely hit it hit a tone that I can get on board with.
Britt: [laughter] You’re our kind of guy.
Devin: Just a particular sense of humor. Which, fittingly, also gets to the fact that this movie balances so much comedy and some really heavy concepts of socio-economic inequality and crumbling relationships. How did you work to balance those tones?
Britt: A big part of the mix we hit is because Kestrin is also an editor, so she really knows how things are going to cut together when we’re shooting them. She made sure that every scene had modifications that she could puzzle piece with when she got into the editing room. That way, when we were all working together on the edit, we could see what landed. We could see where we needed to pull back or push ahead and we would have a new option for each. That ease also came in everyone’s malleability, their ability to know their character so well and to change in the moment when it was asked of them.
Michael: I had the great fortune of producing a movie with Allison Janney a few years ago. I would watch her come on set every day and just rehearse the fuck out of the scene, and then just be shit in her first take to get the nerves out. And then every scene she would do, let’s say we’re imagining the scene as the color red, I would watch her hit every tone of red possible. I’m sitting there on set going my god, this is an editor’s dream because this will all flow so well together.
I kept thinking of that while I was writing and then on set for Pretty Problems, kept thinking about how to try and hit all those shades of red. I just want to make sure that my therapists will like it you know? [laughter] To make sure that it would be funny but also hurt a little bit. I didn’t want to write Marriage Story, but I also didn’t want to write American Pie. So really I’m just so so so happy with how everyone showed up and threaded the needle between the two things. I’m really so impressed and so grateful for all the work everyone did.
[Author’s Note: At this point, my very loud but loving cat Rudy crashed the interview, and Michael, Britt, and I went on a roving tangent about pets, therapists, and, believe it or not, Philip Larkin’s poetry. We finally got it together about 10 minutes later]
Devin: Now that Rudy has decided to behave, I want to ask you both what you’re thinking about as we get close to the SXSW premiere. What are you hoping people can walk away from the movie with?
Michael: Look, I started writing this because I could feel my marriage starting to fracture, to be perfectly honest. I want people to laugh their asses off. That’s for sure. I want them to laugh. I also hope that it can help people with their relationships. You know, we got this really lovely text from J.J., who plays Cat. She shared the movie with a friend. Then that friend texted her back and said, “I think that movie just saved my relationship.” That floored me and made me so fucking happy. So, in a dream way, that’s what I want people to walk out with. I was hoping to save my relationship with this movie, and I didn’t, unfortunately. But, I want people to walk out of this laughing. And also be willing to forgive, love, and see their partner for the whole person they are.
Britt: We never set out to have a solution at the end of this film. We wanted people to wonder. I mean, are they gonna make it? We don’t know. But we know that they are now in a better position to try. It’s getting at this idea of what do we really want out of life? How can I decide to make a change? We so often put the power in other people’s hands, thinking this person is going to change my life. This trip is going to change my life. This business venture is going to change my life.
But, you are the person who has to change your life. We hope you get to laugh at a time when everybody really needs to laugh. And we also want everyone to feel a little bit of hope and a little bit of purpose. You know, a little bit of like, oh, maybe I’m gonna go do that thing I always wanted.
Michael: Amen to that
Devin McGrath-Conwell holds a B.A. in Film / English from Middlebury College and is currently pursuing an MFA in Screenwriting from Emerson College. His obsessions include all things horror, David Lynch, the darkest of satires, and Billy Joel. Devin’s writing has also appeared in publications such as Filmhounds Magazine, Film Cred, Horror Homeroom, and Cinema Scholars.