An unconventional adult love story oozing with awkward charm, Pretty Problems manages to steadfastly churn entertainment from relatable dumb-couple issues and privileged, borderline-satirical rich-bitch characters. For a movie that opens with an unsatisfying sex scene in which both leads settle for a “good try” before soldiering on with their day, I was genuinely surprised at how much I ended up loving both Jack (Michael Tennant) and Lindsey (Britt Rentschler). Directed by Kestrin Pantera with a script from Rentschler, Tennant, and Charlotte Ubben, Pretty Problems is a breezy comedy that gave me exactly what I needed. Money doesn’t fix your problems, it just makes them prettier…
Jack and Lindsey are not only lacking in their sexual fire, but also in their unfulfilling jobs—Jack works as a door-to-door salesman still on probation, whilst Lindsey’s day-to-day consists of enduring a dead-end boutique gig that serves high-end customers room temperature rosé. When Lindsey meets Cat (J.J. Nolan), the couple is sucked into a vortex of wealth and elitism. An exclusive invitation to a private Sonoma chateau carries with it the promise of secret intent. Do Cat and her snooty friends plan to engage in some weird sex orgy, or is it just “some weird rich person thing?”
A weekend of “wine and whimsy” at a vineyard turns out to be the perfect recipe for rekindling Jack and Lindsey’s eternal flame. They are instantly thrown off, since it just happens to be Cat’s birthday, and no one informed them ahead of time. The chemistry between the central players lets the sharp script sizzle with clarity. Some of this dialogue was so preposterous yet rang true, like Lindsey saying “Jack has a great dick, but it’s husband dick.” The cockiness of the affluent friends could easily rub one the wrong way, but at least they seem self-aware of their own privilege.
An impromptu theatrical-style improv play colors the back half of the movie and ends in properly dramatic flair. Possibly my favorite moment of the entire film is Jack’s argument with a pretentious planner—through a series of miscommunications, Lindsey accidentally committed them to two cases of $300 wine bottles, and there are absolutely no refunds. Suffice to say, anyone who has pulled the trigger a little too quickly on a splurge purchase can relate to Jack’s frustrated plight.
Pretty Problems carries that fresh indie charm I love to see at a festival, and there is something comforting in its silly satire of a wealthy lifestyle. I saw one character as an obvious copy of Annie Murphy’s Alexis in Schitt’s Creek, and even this felt in loving tribute rather than a lazy imitation. Maybe money cannot fix one’s problems, but it certainly makes for a cute little love story with a clever screenplay. Pretty Problems carries that in spades.
Pretty Problems debuted at 2022’s SXSW Film Festival.