Review: ‘Pretty Problems,’ starring Britt Rentschler, Michael Tennant, J.J. Nolan, Graham Outerbridge, Charlotte Ubben and Alex Klein

March 27, 2023

by Carla Hay

Britt Rentschler, J.J. Nolan, Graham Outerbridge, Alex Klein, Charlotte Ubben and Michael Tennant in “Pretty Problems” (Photo courtesy of IFC Films)

“Pretty Problems”

Directed by Kestrin Pantera

Culture Representation: Taking place in California, the comedy/drama film “Pretty Problems” features a nearly all-white cast of characters (with one African American) representing the working-class, middle-class and wealthy.

Culture Clash: A middle-class married couple looking to spice up ther lives are invited to a party retreat at a vineyard by a flaky rich woman, who introduces the couple to the equally flaky people in her inner circle, including her husband and another couple of shallow partiers.

Culture Audience: “Pretty Problems” will appeal mainly to people who are interested in watching repetitive movies about people who get drunk at upscale retreats.

Britt Rentschler and J.J. Nolan in “Pretty Problems” (Photo courtesy of IFC Films)

A satire such as “Pretty Problems” could have been a clever parody of shallow and materialistic people, but this tiresome movie ends up being as vapid and annoying as the characters it is trying to mock. Watching this movie is like being stuck somewhere for 103 minutes and watching nothing but people acting stupidly drunk and thinking that they’re hilarious. It’s an endurance test, because there’s almost nothing in this movie that is truly unique, while the characters just aren’t interesting. The one-note jokes quickly run out of steam very early in the film. “Pretty Problems” had its world premiere at the 2022 SXSW Film Festival.

Directed by Kestrin Pantera and written by Michael Tennant, “Pretty Problems” strains to keep the comedy momentum that it seemed to have started in the film’s first 15 minutes. In the beginning of the movie, viewers see that married couple Lindsay Simpson (played by Britt Rentschler) and Jack Brown (played by Tennant) are stuck in a rut in their relationship. They aren’t breaking up, but they’ve become a little bored with each other. The movie begins with a sex scene of Lindsay and Jack in bed together and being “out of sync” and not connecting the way in the way they did when they were happier in their relationship. And then, Lindsay and Jack are shown masturbating separately in the shower.

Lindsay works as a sales clerk at a trendy women’s clothing boutique. Jack works as a probation officer. They don’t have children. One day, when Lindsay is at work, a wealthy homemaker named Catherine “Cat” Flax (played by J.J. Nolan) is in the store and strikes up a friendly conversation with Lindsay. The next thing Lindsay knows, Cat has convinced Lindsay to go on her lunch break with Cat. In the back patio, Lindsay and Cat have some wine (one of the many “Pretty Problems” scenes where the characters are drinking alcohol), and they talk about their lives.

Cat is married to a self-made billionaire businessman. They have twin children, who are never seen in the movie. Cat tells Lindsay that Lindsay looks too smart to be a retail sales clerk. Lindsay admits that her dream is to have her own fashion business, with either her own brand of designer clothing or a high-end retail store. Even though they’ve just met, Cat offers to invest in Lindsay’s dream. And that’s how Lindsay finds out that Cat is rich.

But is Cat’s generous offer for real, or is it just drunken rambling from a bored woman with a lot of money? When Cat goes back into the store, she spends a long time lingering and being somewhat of distraction to the store employees. Finally, Lindsay’s supervisor Georgia tells Lindsay: “If your friend isn’t going to buy anything, I’m going to ask you to leave.” Cat then proceeds to buy a massive number of clothing in the store, so that Lindsay can get the credit for selling the merchandise.

When Lindsay is at home with Jack, she enthusiastically tells him about Cat and how they became “fast friends,” as well as the large purchase that Cat made to help Lindsay look like a great salesperson. Lindsay says to Jack: “I sold more in that boutique in six minutes than I sold in six months.” Lindsay also tells Jack that Cat has invited them to an adults-only party retreat at a vineyard in Sonoma, where Cat and her husband have one of their homes.

Jack is skeptical because he thinks that he and Lindsay won’t fit in at this retreat. He’s not just skeptical. He’s also paranoid that they might be targeted to join a weird sex cult. Lindsay is excited and intrigued and says she wants to go to this retreat, with or without Jack. After much whining and hesitation, Jack agrees to go with Lindsay to the retreat. They take their car for the road trip to the vineyard.

When they get to the vineyard, Cat is drunk (as usual) and introduces Jack and Lindsay to her husband Matt Flax (played by Graham Outerbridge), who proceeds to tell Jack that Matt recently bought Jack’s favorite beer distributor. Jack and Lindsay are then introduced to the other couple who are part of this group retreat. Carrie (played by Charlotte Ubben) is a ditzy model/actress, who is the latest fling for Kerry (played by Alex Klein), who is living of off his family’s trust fund. Kerry’s grandfather invented Tater Tots. One of the first things that Carrie and Kerry do after they meet Lindsay and Jack is brag about spending $65,000 on champagne and cocaine.

The rest of “Pretty Problems” is just a series of scenes showing these six partiers getting intoxicated, having mindless conversations (where there’s more boasting and flaunting of wealth and possessions), and making fools out of themselves in various ways. There are some very unoriginal scenes where the group has a “murder mystery game” and then do some karaoke. Lindsay is eager to fit in with this group, but Matt starts out as very uptight and acting like he’s above all the drunken antics. And then, someone puts Ecstasy in Matt’s drink without his knowledge or consent, and he starts acting like an idiot too.

Meanwhile, the employees of Cat and Max have to deal with serving these partiers and staying calm and rational as things get more chaotic. Dan (played by Clayton Froning), who works for the Flax couple as a majordomo, is a former Sea World trainer. He also happens to know Lindsay from when they were in high school together, and he had the name Big Dick Dan. It’s so predictable what kind of history Lindsay has with Dan and what Matt’s reaction will be when he finds out.

Other employees include party planner Becca (played by Katarina Hughes) who is a Rhodes Scholar playwright; master sommelier Georges (played Tom Detrinis); and shaman Gigi (played by Vanessa Chester), who leads a meditation session like a teacher has to lead a classroom of unruly kids. There is nothing special about any of the performances in “Pretty Problems.” In fact, some of the cast members over-act and therefore ruin what could have been hilarious satire.

It doesn’t take long for “Pretty Problems” to run out of ideas after making its point over and over that rich jerks who are drunk or high on drugs are still jerks, but the drinking and drugging just amplify their awful personalities. “Pretty Problems” might have been better off it were filmed like a mockumentary short film, but it still wouldn’t erase the movie’s unremarkable acting and dull dialogue. If people want to see a witty and dark satire of wealthy people behaving badly in gorgeous settings, then viewers are better off watching HBO’s “The White Lotus.”

IFC Films released “Pretty Problems” in select U.S. cinemas, on digital and VOD on October 7, 2022.

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