‘Pretty Problems’ Review: A Brief, Bruising Climb Up the Social Ladder

Class divisions that assume macrocosmic significance in Ruben Östlund’s “Triangle of Sadness” remain microcosmically scaled in “Pretty Problems,” another cleverly discomfiting, festival-blessed comedy hitting theaters on Oct. 13. Kestrin Pantera’s third directorial feature, which won the Audience Award at SXSW, also places a less-advantaged young couple in an enclave of the very rich. Here, however, the upscale slumming is not free, but rather at their expense — a cruel-gamesmanship setup that (as our hero duly notes) suggests the usual horror-movie agenda of “They’re gonna kill us.”

That teased direction is not where the film eventually goes, and indeed the script (hatched by several lead performers here) manages to keep upending expectations to the end. The result is a fresh mix of social satire and relationship dissection with a saving dollop of heart. IFC is opening it on about 30 U.S. theater screens, simultaneous with on-demand platforms. 

Opening with a sex scene in which both parties are fine with quitting halfway — one participant’s “Good try!” sounding like a nail in the marital-bed coffin — the film immediately makes clear that all is not well between Lindsay (Britt Rentschler) and Jack (Michael Tennant). For starters, they both hate their jobs: She sells other people’s clothes when she’d hoped to design herself; he hawks solar panels to residents who mostly slam their doors in his face. They’re not poor, but they’re not where they thought they’d be, and prospects aren’t bright. 

So it is extremely cheering to Lindsay when a stray patron at her unpleasant boss’s shop takes a shine to her. More than that, the flamboyant, impulsive and very wealthy Cat Flax (J.J. Nolan) insists her new BFF and spouse be guests for “a weekend of wine and whimsy” at this benefactor’s Sonoma County home. Jack finds the whole thing dubious. Nonetheless, they are soon pulling up to the gated rural property, which is surrounded by vineyards and crammed with expensive artwork and other luxury items inside.

Cat and husband Matt (Graham Outerbridge) are celebrating her birthday — an occasion they’d neglected to mention — with just one other couple, his prep-school bud Kerry (Alex Klein) and latest girlfriend Carrie (Charlotte Ubben). The hosts have twin children, but they have been packed off with an au pair so the grown-ups can party. Which they do with a vengeance, and not always with full advance disclosure. (That is an issue because ex-lawyer Jack got disbarred due to a criminal offense he’s still on probation for, complete with regular drug testing.) 

There is a very full three-day schedule of planned excesses, abetted by resident servants Becca (Katarina Hughes) and Dan (Clayton Froning), the last of whom Lindsay just happens to have known in high school. Indeed, there are many other things the Flaxes already seem to know about their less well-heeled guests. Enough to make Jack, in particular, wonder if they’ve been lured here as something like human toys, their minds and bodies to be played with. Certainly each bruisingly decadent day ends with the newcomers ever more at odds with each other, their secrets ferreted out and displayed for all to see.

It is much to the credit of first-time feature screenwriter Rentschler (who shares story credit with co-stars Tennant and Ubben) that the amusingly outré situations never quite exceed plausibility, and that characters close to deft caricature likewise keep revealing themselves as more complicated — even if they never reveal themselves fully. Perhaps the most surprising thing about “Pretty Problems” is that it stealthily acquires enough depth to pull off an upbeat fade-out, one that credibly rewards our protagonists rather than handing them the anticipated booby prize. That lack of cynicism is all the more pleasing for being so unanticipated in a movie that can encompass lines as snark-drenched as “You’re like a clown car on the way to a Chris Gaines concert.”

These actors are all very good in roles they palpably had a hand in shaping. (Some closing-credits scenes hint at a degree of improvisation involved.) For director Pantera, the expertly handled tonal shifts and smooth presentation are a big positive leap from her last feature, “Mother’s Little Helpers,” a clumsy 2019 dysfunctional-family serio-comedy that also premiered at SXSW. “Pretty Problems” also reps an impressive feature debut for cinematographer Alyssa Brocato, while other notable contributions in a strong overall assembly are from production designer Ken Fulk and music supervisor Rentschler.