‘Pretty Problems’ Review: Rich People Get Very, Very Wine Drunk in Fizzy Hangout Comedy

Christian Zilko
·5 min read

Sometimes, the grass really is greener. That’s a lesson that Jack and Lindsay (Michael Tennant and Britt Rentschler) learn in “Pretty Problems,” though it’s not like their side of the fence was offering much competition. The young married couple is stuck in the kind of rut that nobody expects to hit at such an early age. She’s a wannabe fashion designer who had to put her dreams on whole and work a retail job, while he’s a lovable schlub selling solar panels door-to-door while making sure his probation officer (who’s tragically named Doug) doesn’t send him to jail. They have a nonexistent sex life despite their best efforts, and appear to be floating in a kind of domestic purgatory that isn’t easily escaped.

That all changes when Cat (JJ Nolan) wanders into the boutique where Lindsay works. The vape-loving, wine-guzzling trophy wife is everything that Lindsay isn’t: free-spirited, glamorous, and completely unburdened by the daily mundanities that accompany the necessity of earning a living. The two women strike up a conversation about fashion, and Lindsay soon decides to buy one of every item in the store. And if the massive commission wasn’t enough of a gift to Lindsay, she invites the couple to spend a weekend with her and her billionaire husband Matt (Graham Outerbridge) at their vacation home in Sonoma County. Jack is understandably concerned that accepting a total stranger’s invitation to an off-the-grid mansion is an easy way to get murdered, but eventually agrees to go.

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When they arrive, they quickly realize that their new rich friends are even richer than they thought. Brad and Cat live in a mansion that would make Jay Gatsby blush, complete with multiple guest houses, servants on hand to take care of their every need, and vineyards as far as the eye can see. The guest room is even stocked with lavish gift bags full of weed, lube, and custom bathrobes embroidered with bad classic rock puns. It turns out that they’re here for Cat’s birthday weekend, with Cat telling Lindsay that she invited them because she despises the other two guests (an heir to a tater tot fortune and his influencer girlfriend). She needed someone from outside her wealthy bubble to balance things out—which is rather ironic, considering the weekend’s itinerary costs more than a small country’s GDP. The party guests sip rare tequilas that aren’t sold on the open market, go to a wine tasting with $300 dollar bottles before deciding to buy two cases of everything, attend private yoga classes and healing sessions, and ultimately end the weekend with a drug-fueled silent rave.

Based on that premise, you’d be forgiven for thinking that the wine country weekend will eventually devolve into some kind of “Eyes Wide Shut” horror show or a “Succession”-like display of rich people being assholes. But the party rages on without a major twist and “Pretty Problems” never comes close to reaching either extreme. As far as ultra-wealthy characters go, Matt and Cat are actually pretty difficult to hate. He’s as close to a “self-made billionaire” as anyone can be, but still readily acknowledges the multitude of lucky breaks that helped him make his fortune. And she may be a frivolous spender who lives a comically excessive lifestyle, but she’s always ready to open her checkbook at a moment’s notice to help a friend. They treat their staff nicely and pay them even more nicely — in many ways, their greatest sin is wasting copious amounts of money that they can clearly afford to waste. Sure, they’re two bulls who treat the world like their own personal china shop, but they’re always ready to reimburse the owner for the damage they caused (plus a little extra for his troubles).

So anyone expecting “Pretty Problems” to turn into a biting satire about wealth will be sorely disappointed, as the script brings a melon baller to a knife fight on the few occasions when it dips its toe into social commentary. Kestrin Pantera’s film is much more interesting when it explores Lindsay and Jack’s reaction to the way the other half lives. The opulent displays of wealth serve as a Rorschach test for their stagnant marriage, with Lindsay admitting how badly she wants to live in this world and Jack realizing that he’ll never be the kind of partner who will get her there.

The dynamic between the two of them is refreshingly human: their life goals and means of reaching them are increasingly at odds, but they’re still bound together by a genuine love that’s apparent in every scene. Their discussions about their marriage have less to do with the pros and cons of wealth than they do with the tradeoffs that it takes to build it. The film leaves a few of those threads unexplored and rushes the couple to an overly simplistic conclusion at the end, but the plane had to land at some point. Nobody has ever walked out of a comedy wishing that it was 25 minutes longer and more morally grey.

Because make no mistake, “Pretty Problems” is a comedy in every sense of the word. Even if Tennant, Renschler, and Charlotte Ubben (who co-wrote the film in addition to starring in it) fell short of their satirical ambitions, they wrote a pretty great hangout movie in the process. “Pretty Problems” is the kind of film we don’t see nearly enough of: a competently executed, unapologetically adult comedy that never takes itself too seriously yet refuses to phone it in. Rich people might live in a world without consequences, but “Pretty Problems” reminds us that it can be pretty damn fun to join them for a couple hours.

Grade: B+

IFC Films will release “Pretty Problems” in select theaters and on demand on Friday, October 7. 

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