Pretty Problems’ protagonists Jack (Michael Tennant) and Lindsay (Britt Rentschler) are in desperate need of some life changes. They both work unfulfilling jobs: door-to-door sales for Jack, and being berated by the ultra-wealthy at a bourgeois boutique for Lindsay. They love each other, but they are not obsessed with each other. After giving up on an attempt at morning sex, Lindsay masturbates in the shower, and Jack masturbates in bed. They’re capable of pleasure once in their separate corners but are just not able to access that spark together.
This opening sex scene is actually one of the more interesting moments in the film, representing both Lindsay and Jack’s capacity for desire and their inability to push themselves out of their rut. An opportunity for temporary change appears in the form of the ultra-wealthy, peppy, sardonic Cat (J.J. Nolan), who bursts into Lindsay’s bland job and life. After a pleasant conversation, she unexpectedly invites her to her birthday weekend out in wine country. Lindsay convinces a hesitant Jack to join, and the two embark on a fish out of water tale, trying their best to keep up with the debauchery of the very, very rich.
Pretty Problems feels like it’s trying to be both an incisive dig at the filthy rich and a classic story of a couple trying to jolt some spark (or motivation to even live slightly better) into their lives. Oftentimes, however, the film’s writing feels a bit stiff and broad on both fronts. Cat and her super-rich friends swing between total vapidity and a strange amount of self-awareness, sometimes bringing up their own immense privilege, sometimes being shockingly out-of-touch (compared to Jack and Lindsay) in a way that makes them sort of generally uninteresting.
The group partakes in a variety of unhinged behavior — destroying their home, getting very drunk, demanding too much of their staff — but none of it has much of a bite. One wishes that the protagonists’ fears at the beginning of the film (that the weekend might turn into some wild sexual debauchery or even something horrific) would come true. Instead, however, the two just end up in a group of people that are undoubtedly strange, but not enough so to be shocking, titillating, or all that interesting. They mostly just drink and have unfulfilling relationships without any additional stressors.
The weekend places a strain on Jack and Lindsay, as she constantly tries to fit in and be something that she isn’t while he often insists — sometimes too much so — on bringing her back down to earth. While they seem like nice enough people, they don’t necessarily share much chemistry.
As the weekend progresses, the couple seems to go through the same little arc over and over: a spat, followed by working it out, and another spat, followed by working it out. No astronomical conflict comes to a head; in fact, the few moments that feel like they could be big problems (the reveal that Cat has been putting shrooms in their food and drink the whole time, or Jack breaking his probation rules by getting into a fight) are so rapidly resolved they’re practically rushed.
While one can appreciate that Pretty Problems is working to take some well-deserved shots at the very rich, it ultimately doesn’t give one much to hold onto throughout. Instead, it opts for a story of small tensions and easy, rather pedestrian resolutions between a couple, and only presents the idea of commentary on the ultra-wealthy without ever going beyond some pretty neutral, inoffensive caricatures.