People often fall in love with the potential of new relationships, both romances and friendships, until they’re eventually faced with the truth about the actual circumstance of the other person’s life. The protagonists of the new romantic comedy-drama, ‘Pretty Problems,’ down-on-their-luck married couple Lindsay and Jack, feel as though they may not to be able to grow as a couple any longer. They then meet several wealthy couples who initially appear to be able to help improve Lindsay and Jack’s lives, until the duo eventually realizes they must put in the work themselves in order to find happiness together again.
The film was written by producers Michael Tennant Britt Rentschler and Charlotte Ubben, who also all star in the feature. Kestrin Pantera served as the director on the movie.
‘Pretty Problems’ had its World Premiere in the Narrative Spotlight section of this year’s SXSW this past March. The comedy-drama went on to win the Austin-based festival’s Audience Award in the Narrative Spotlight category following its premiere.
‘Pretty Problems’ follows Lindsay (Rentschler) and Jack (Tennant), who are stuck in a rut, both professionally and in their marriage. They hope they can revive their lives when they’re invited for a long weekend in wine country by Cat Flax (JJ Nolan), a very wealthy housewife who quickly befriends Lindsay while shopping in the clothing store the latter works at.
Upon arriving at the big glass house on top of a hill, Lindsay and Jack are introduced to Cat’s husband, Matt (Graham Outerbridge), a self-made billionaire who freely emphasizes how successful he is whenever he can, and how privilege has provided for him. Along for the weekend are Carrie (Charlotte Ubben), an actress-model-dancer who’s the arm candy of Matt’s best friend, Kerry (Alex Klein), a trust fund kid whose grandfather invented the tater tot.
The staff at the home includes Dan (Clayton Froning), an ex-Sea World trainer-turned majordomo; Becca (Katarina Hughes), a Rhodes Scholar playwright who now plans parties; Georges (Tom Detrinis), a master sommelier; and Gigi (Vanessa Chester), a shaman who is on call and ready to fix all the Flaxs’ short-term problems. Lindsay and Jack’s relationship is put to test over the weekend by the excess of wine and wealth that Lindsay wants, and Jack is afraid of.
Pantera, Rentschler and Tennant generously took the time during this year’s SXSW to talk about penning, helming and starring in ‘Pretty Problems’ during an exclusive interview over Zoom. Among other things, the filmmakers discussed how the script was inspired in part by their desire to discuss the realistic troubles that romantic partners contend with throughout their relationships through a comedic, relatable lens. The trio also shared that even though there are many detailed tasks they have to accomplish in order to bring a film to SXSW, they were honored and excited to be able to premiere the film at this year’s edition of the festival.
ShockYa (SY): Britt and Michael, you co-wrote the script for the new romantic comedy-drama, ‘Pretty Problems.’ What inspired you to pen the screenplay for the movie?
Michael Tennant (MT): It’s funny – the script was actually born in Austin. I was here in 2018, when Mark Duplass gave his “The cavalry is not coming” speech as one of (SXSW‘s) keynote speakers. I snuck into his speech, and I apologized to (VP, Director of Film) Janet (Pierson) at the festival already about this. (Tennant laughs.)
His speech really lit a fire under me. I’ve been an actor for years, and had been working at a production company at the time, doing development. I was getting frustrated with the movies I was seeing getting made, so I thought, I think I can do this.
I’ve known Britt for years; we’ve been in acting class together for a really long time, and really dear friends, in a brother and sister-type of way. So I went to her with a fledgling idea of a married couple.
In my own marriage, I was starting to feel some cracks, and was talking to Britt and a lot of my other friends about their own relationships, so it was something that I wanted to explore. I love comedy, and I also like feelings, so I was hoping to write something that would make people laugh, but also make them hurt a little bit, too, kind of like real life. I then pulled Britt in, and we wrote the script together.
Britt Rentschler (BR): After we finished the script, I unkowningly stalked Kestrin a little bit. We knew we wanted a female director, particularly someone who had a really strong sense of style, but could also get great performances.
We also wanted someone who could also wrangle our wild, wonderful friends, who we all cast in this movie. Something that was really important to Michael was to try not to pick a celebrity, and build a movie around them; it was really to find some authentic relationships between actors who we already knew.
So Kestrin was recommended to us by a wonderful writer friend of ours. I also actually saw Kestrin at Sundance in 2020. I didn’t realize it was her as I was watching her in this fabulous fur coat manage this person who was having a situation. I watched her handle it because I was traveling alone, and I thought, wow, she was so diplomatic and was so positive – that was really cool.
Then months later, I was finally introduced to her during a meeting, and I recognized the jacket from her Instagram. I thought, I know this woman! I didn’t mean to stalk her, but luckily, she still agreed to direct the movie!
SY: Kestrin, speaking of the fact that you directed the film, what was it about the script that convinced you to helm the project? How would you describe your overall directorial style on the movie?
Kestrin Pantera (KP): Well, Britt is a witch who stalked me! (Pantera and Rentschler laugh.) She’s also a master email writer, so she wrote a really kind and direct email, offering me the opportunity to read the script, and check out this amazing location she was sourced. It was put together and ready to go.
So I read the script on an airplane and laughed out loud. I then met Britt and Michael, and realized she stalked me. (Pantera and Rentschler laugh.) So it was impossible to say no to this opportunity to go to Sonoma and live on this amazing compound for three weeks with these talented people.
I did get the opportunity to cast JJ Nolan and Vanessa Chester, two of my friends, and they’re wonderful actors. There was a little bit of wondering how all of these actors, who are from distinctly different friend groups with their own existing rapport, would blend together. But I thought that they did a beautiful job of forming a cohesive unit ensemble. So it was a real joy.
With COVID lasting longer than we expected, we had an extra year to develop the script more than the original iteration. But it was percent there; it was hilarious and amazing. The characters were true and relationships were raw and rife with tension. So it was really about doing these little tweaks.
MT: Kestrin does this really fun thing with actors, especially with the actors who wrote the script; she’ll go up to you right before we shoot the scene and ask if we could change something…
KP: We talked about those things beforehand! If you’re going to give that way, I’m going to give this away: there were a few scenes in the script when I first read it that I flagged, and said they needed to be cleaner.
But I will say, it takes two to tango – we both put it off mutually. I’d be up at night, thinking, I’m really stressed out about this.
BR: There are some things in the movie that are different than the way we initially wrote them. Kestrin’s very collaborative and open to the idea that the best idea wins.
So we would shoot the scenes the way we initially envisioned them, and then she would come in and say, ‘I was a little curious about this scene. What do you think about changing it?’ Then we’d find a way to change it to the way it needed to be in the moment. I think that was kismet, in a way, because things weren’t always pre-packaged or pre-planned. We mostly got what we initially wanted, but then we’d pivot, and that happened very naturally.
MT: That’s what I was going to say!
KP: Thanks Michael! We’d usually shoot scenes the way they were written, and then we’d ask, ‘Does anyone have any joke ideas?’ Then everyone would pitch a joke, and the actors would would unleash their talent, which was the easiest, and my favorite, part.
SY: Speaking about the rest of the ensemble cast, once the other actors were brought onto the film, what was the process like of working with them to build the characters’ relationships?
MT: I had the outline done, and about 10 pages of the script written. We were sitting at my birthday dinner in 2019, and I was looking around the table and saw all of my amazing friends. So I thought to myself, what if I go make a movie with these people? I know that none of these people will let me fall down…and I would do the same thing for them.
Most of the actors in the movie are my friends and acquaintances, including JJ; I had forgotten that we were in acting class together. I’m thrilled that Kestrin brought her back into my life, and she’s become a dear friend of mine.
But we knew most of the actors, so we specially wrote around their talents, Thankfully, Kestrin also gave people the room to play.
She actually brought JJ in to read for the role of Carrie, and Charlotte Ubben was actually supposed to play Cat. But after JJ’s read, Charlotte turned to me and said, “I’m actually playing Carrie.” I thought, I just offered JJ this part, so what do I do? So we put our heads together and thought, what would it look like if she plays Cat? It then couldn’t have been a happier accident.
SY: Like it was mentioned earlier, the comedy-drama was largely shot on one property in Sonoma. What was the experience like of shooting the movie on the property?
BR: It was absolute heaven. We were supposed to go shoot just as everything began to shut down during the beginning of the pandemic in 2020. So we were put on a year hold. Then there were the wild fires that swept through that area of California, so we were afraid that we weren’t going to be able to make the film at all.
Then all of the protocols were put into place by all of the unions, so we were able to put everything into place. We got all of our testing supplies and a COVID officer, and quickly learned how to operate under all of the regulations.
It was magical because we were all living together in the same space, working on something. We were back to work, and back together. We were on a beautiful vineyard in Sonoma, watching the sunsets together. It was as much hard work as it always is working on a film, as we were working from sunup to late nights, but we didn’t mind doing it.
SY: Britt and Michael, besides working on the script for, and starring in, ‘Pretty Problems,’ you both also served as producers. How did you balance your producing and acting duties on the set?
MT: I’d be incredibly remiss if I left out Katya Alexander, one of our other producers, who really did most of the line producing while Britt and I were acting. She was really such a great champion for us, as she fought, and got things accomplished, for us. We were a really tight-knit group. But for Britt and I, there wasn’t a lot of ugly crying…
KP: There was a little!
BR: We were all wearing multiple hats. Michael and I had worked on some shorts together, so we enjoyed producing to a certain degree before. But producing a feature was a new beast. I felt an incredible sense of purpose with it.
I’m so used to someone hiring me, so that I can do my job as an actor. If they don’t like you, they say, ‘Good luck in finding something else.’
So to be able to be the person who says yes, we have a director, and yes, we’re hiring these people, and be the person who build up that energy for other people’s jobs, gave me an incredible sense of purpose. So I enjoyed that more than I’ve enjoyed any other process up to this point in my career.
KP: Both of them are natural producers and wonderful people to work with.
MT: She actually had to make us turn our producing off sometimes because we were so caught up with it. At one point, Kestrin had to yell at me, “Michael, stop tying everyone’s shoes and come stand in front of the camera!”
KP: I would have to say, “You need to get on set and go act!”
SY: ‘Pretty Problems’ (had) its World Premiere in the Narrative Spotlight section of this year’s SXSW, hich you mentioned before, Michael. What does it mean to you all that the comedy-drama (premiered) at the festival?
KP: Preparing for SXSW is usually Herculean effort because you’re doing a million different things. The movie wasn’t finished yet, as we hadn’t done our sound and color, and we were also figuring out what jokes to keep in the movie.
Fortunately, I’ve had a film go to SXSW in 2019, so at least I had a sense of what was to come, and the milestones that you go through. You have to deliver on this day, you have to get this done by this day. I had all of my old spreadsheets. So this time around, it felt so much smoother because at least I knew what to expect, and I was able to share the spreadsheets everyone.
BR: I didn’t even know to make a spreadsheet on Google Drive, so having that was incredible! It held everything together.
MT: These two love their spreadsheets! I didn’t even know how to use them.
BR: We love the organization!