Katya Alexander on Pretty Problems

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Katya Alexander is a multi-award-winning producer who aspires to define comedy for this generation. Her most recent work includes Pretty Problems, a comedy about a couple ends up on the most unhinged weekend of their lives set to release in October 2022, and The Mirror Game, a film about 2 childhood friends that have a life changing weekend. 

In our latest Anatomy of a Scene interview, Katya breaks down one of her favorite scenes from Pretty Problems.

PH: How did you get involved in the film Pretty Problems? Tell us a bit about your relationship with the lead filmmakers.

Katya Alexander: I keep saying that this team is like lightning in a bottle. It’s rare to work so well with people both creatively and technically. Michael Tennant ultimately had the idea for Pretty Problems. He wrote the first 15 pages, brought that to Britt Rentschler, and she said, “We absolutely have to make this.” 

I knew Michael from a studio that we both worked at together. We kept clocking each other as people who lived to tell stories and were capable of getting things done. Six months after working there, Michael reached out to me about producing this other feature The Mirror Game. The day we wrapped that movie, Michael called me and told me about Pretty Problems. I read it and had the same reaction as Britt, “Oh my god! We have to make this!” 

Britt met Kestrin Pantera at the airport coming home from Sundance and knew she wanted her to direct it. Three and a half months later, we were on set saying “action” for our first take of Pretty Problems. The entire movie happened because of fate, and a significant amount of hard work. The stars aligned on this one. 

PH: Which scene was your favorite in Pretty Problems?

Katya Alexander: I have two favorite scenes, my favorite scene to film and my favorite scene to watch. My favorite scene to film was definitely the pool scene. It happened about two-thirds of the way through the shoot, and it was exactly what we needed. The entire crew jumped in the pool at one point, and it felt like having a pool party while filming a movie. 

My favorite scene to watch is most definitely the murder mystery party. The costumes are incredible, the acting is amazing, and it’s the scene that the crew and I quote the most to this day. It’s a moment where everyone in the cast really shines.

PH: Describe this scene and the significance it has to the rest of the film?

Katya Alexander: The murder mystery scene is where everything comes to a head. Jack snaps after holding his feelings back for the entire movie and embarrasses Lindsay. It puts the audience in this position where they understand why Jack snaps but he also didn’t handle it well. It works with the general theme of the movie that there isn’t a villain. Just like in real life, the villain is often ourselves.  

The pool party comes after the murder mystery. Matt reveals some game-changing information to Jack as they’re drinking in the pool. This scene is interesting because we rewrote it before we filmed it. We were constantly trying to find the best ways to make things work and our motto was “best idea wins.” The rewrite of this scene allowed us to make some subtle changes to the end of the movie, which I think had a part in the film’s success. 

PH: In the development process, what were the keys to making the film a success both on set and in the final product?

Katya Alexander: I heard this piece of advice a long time ago, and it really stuck with me. “Get notes early and often.” Michael and Britt wrote the film and Kestrin directed it, and they deserve the credit for that, but the film as a whole was a team effort. Before the three months of heavy pre-production, we hosted countless table reads, and that continued through pre-production. It allowed us to hear the movie be acted out and decide what actually worked, what jokes landed, and whether it’s coming across how we wanted it to. 

During production, we had live dailies and an editor. We were meeting with the actors every night during dinner, talking about what their characters were going through and why they were making these decisions. We didn’t shy away from rewriting scenes before we shot them. We even re-shot some scenes that we didn’t feel were working after seeing them edited. We were constantly thinking, “How can this movie be better?” It definitely helped that Michael starred in the movie, so he was always around to do rewrites.  

In post, we did this insane process of editing all day, hosting a test screening at 8 PM, getting their notes until 1 AM, Kestrin would edit from 1 AM – 9 AM, our editor, Grant McFadden would edit until 7 PM, and then we would host another screening with a new audience at 8 PM. We did that for two weeks straight before submitting to SXSW, and then we did that again to reach picture lock. The audiences we brought in were from all walks of life, different careers, different interests….etc. I think it’s why the movie has such a wide appeal. 

To show how it’s never too early to get notes, for our first screening, the movie was over two and a half hours long. Don’t be embarrassed and be open to different opinions. 

PH: What technical challenges did you or the film encounter as it came together? How did you overcome it?

Katya Alexander: This is an insane story. One of our cameras broke during our first week of production. I had to source a new camera to arrive by shooting the next day. I had our AC pick one up an hour away in San Francisco that morning. The problem with San Francisco is that the cameras are more expensive there, so we could only get it for a single day.  

I had my friend pick up a camera in Los Angeles and fly it to our set in Sonoma to cover the rest of the shoot. There was a bit of a mix-up and he went to the wrong airport. He was now scheduled to arrive at the correct airport five minutes after the plane was supposed to take off. I was like “just drive!” We called the airport and tried to see if they would hold the plane. The rental house in San Francisco is calling me at the same time, asking for the camera back and I’m begging them for three more hours with it. After a lot of coaxing, they finally agree. I get a picture of my friend on the plane, camera in hand. I almost fell to my knees right there. 

It was so perfectly timed, my friend arrived on set and handed the ACs the camera as my ACs were handing off the loaner camera to be driven back to San Francisco. It was one of those moments where I was like everything worked out and all that we had to do was stop a plane. 

PH: Are there any other fun anecdotes from the development of Pretty Problems?

Katya Alexander: Pretty Problems had so many false starts. It was originally supposed to film in the spring of 2020, so I wonder what happened there. Then during the pandemic, the location almost burned down. Our original cinematographer became a mother and had to drop out of the movie. The early stages of making a movie are always an uphill battle, but then all of a sudden we had Alyssa Brocato to film the movie. The location became available while all of the actors and crew were available. My best friend Galileo Mondol was able to loan us his camera equipment and source all of the other equipment we would need. The clouds parted and the planets aligned.  

I think about all of the obstacles and then I think about sitting by the pool on our days off from filming and pieing each other in the face. I think about sitting in the hot tub with the crew each night after a wonderful day of filming. I think about sharing the stage with almost the entire crew of the movie at SXSW. I think about Michael, Britt, Kestrin, and I standing in a circle and just staring at each other in disbelief at what has happened with this movie. I always try to remember that it always works out and is always worth it. If you’re thinking you want to make a movie or you have a story to tell, please go make it and go tell it. 

PH: What do you hope audiences take away from this film?

Katya Alexander: Pretty Problems is such a fun film, but it’s also about relationships and love. It’s about comparison being the death of joy. My favorite thing about comedy is that it’s a fun way to get a message out there. This movie has so much heart. I’m excited for people to laugh and cry. As we say, “you’re invited to question all your life choices.” 

PH: What is next for you?

Katya Alexander: I’m working on some projects I’m extremely excited about. We’re getting the band back together and I’m developing a couple more films with Michael and Britt. I’m also developing some projects with people I met before Pretty Problems and after it. I’m really looking forward to being able to speak more about them soon.

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