Lindsay and Jack are bored. Bored of each other and their dead-end jobs; bored of being 30-somethings who lives aren’t really going anywhere. When Lindsay’s normal, boring work day at an uppity retail boutique is interrupted by the weird and charismatic Cat, things instantly seem like they might begin to change for the couple.
It turns out that Cat is bored too. After purchasing everything (actually everything) in the store Lindsay works at, she invites Lindsay and Jack to come to Sonoma with her and her husband. Jack’s skeptical: is this a rich person sex thing, a Purge thing perhaps? Well, we’re about to find out.
When Lindsay (Britt Rentschler) tells Cat (JJ Nolan) that she is stuck working her retail job because of student debt, Cat genuinely looks confused and concerned. It’s little moments like this that make Pretty Problems so on–the-nose funny; why would a wealthy person understand student debt?
The two women have chemistry together; while we’re not sure what exactly Cat wants, or where this dynamic will end up, it’s fun to watch the two of them together. We can’t be too sure what Cat’s motivations are, and if there is something nefarious behind her invitation. There’s a light tension that’s well balanced against the otherwise comedic story.
At the Sonoma gathering, there’s Jack and Lindsay, Cat and her (also uber-wealthy) husband Matt, and another couple, Carrie and Kerry. This group (minus Jack and Lindsay) truly epitomizes cringey, tone-deaf, wealthy white folks. Of course, Cat and Matt do have staff present; a lot of staff.
They flaunt their wealth in a truly oblivious way – although they know that Jack and Lindsay are not on the same level (or even close), they don’t bother to pretend to be humble. At some point, Lindsay starts acting like her and Jack are on the same monetary wavelength as the other two couples, even though that clearly makes Jack (Michael Tennant) very uncomfortable.
Pretty Problems does a lot with a fairly small cast — something I’m sure that we’ll see more of in films made during the last few years. The unique creative restraints that have been placed on filmmakers as a result of the pandemic seem to often work like a creative writing exercise — within these constraints, how can we make this work? The cast was quarantined together, which certainly paid off in terms of the clear chemistry everyone has together. They might all really be friends who hate each other, just a little bit.
Carrie (Charlotte Ubben) provides some comedic relief that isn’t really necessary. She’s a sloppy drunk who Cat (not-so-secretly) can’t stand. She’s goofy and a bit too over-the-top. The movie is plenty funny without her, between Jack’s blatant discomfort, Cat’s constant vaping (with a vape pen to match each outfit) and the excess of alcohol-fueled antics. Carrie’s boyfriend, Matt’s best friend Kerry (Alex Klein) is actually really funny. He’s weird and over-the-top too, but in a more natural way that fits right in with this weird weekend.
The cringey-ness is turned up a notch when Cat requests the group’s presence at a cacao ceremony in the garden, lead by Gigi (Vanessa Chester) a beautiful black woman in a crown of quartz crystals. With the group all wearing white linens and sipping their cacao, it’s a bit of a Nine Perfect Strangers moment as they all chant “I love you, I’m sorry, please forgive me”.
It’s a bit off-putting that the only person of color in the film is Gigi, but maybe we can give director Kestrin Pantera and writer/actor Michael Tennant the benefit of the doubt here: this is, after all, a cynical look into the lives of elite white people who take themselves too seriously.
While the wealth gap expands and most of us don’t know people who name-drop “Elon” and “my friend Brené Brown”, most viewers will find themselves relating to Jack or Lindsay, at least a bit. Jack is uncomfortable and really wants nothing to do with “these people”; Lindsay longs to be more like them.
How will their relationship survive this weekend? It’s the kind of movie that viewers will find themselves asking themselves what they would do in this situation — how they would react. Most people would never end up in this situation in the first place, which is exactly why this is a fun movie to watch.
Pretty Problems makes it’s world premiere on March 14th at the SXSW Film Festival as a Narrative Spotlight.
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