‘Stella’s Last Weekend’ Film Review: Brothers Nat and Alex Wolff Play Siblings in Love with the Same Girl

Actress-filmmaker Polly Draper skillfully directs her actor sons in a low-key comedy about heartbreak and loss

Stella's Last Weekend

Trigger warning: The title of “Stella’s Last Weekend” refers to a dog’s final hurrah before she’s put to sleep. Her family thought it would be nice for her to be surrounded by other dogs, so they have a party. Stella is bedecked with a halo. It’s meant to be a merely melancholy occasion, but for certain viewers it may be gut-wrenching.

Of course, if you’ve ever been in love with your best friend’s girl, your stomach may sink during other parts of the film as well.

The best friends in writer-director-actor Polly Draper’s charming romantic comedy are brothers Jack and Oliver (real-life brothers Nat Wolff of “Paper Towns” and Alex Wolff of “Hereditary,” respectively). Jack comes home from college for his dog’s party, while Oliver is still in high school living with their mom (Draper, also the actors’ real-life mother). Immediately their rapport is evident, with the guys falling into easy joking, including sexual wisecracks about Mom and her current boyfriend, Ron (Nick Sandow,”Orange Is the New Black”). A scene at the table soon after shows that they don’t hold back to their mother’s face, either. “You are one batshit crazy bitch, aren’t you, Mom?” Oliver says, much to the squarer Ron’s displeasure.

Ron proves to be a thorn in the brothers’ sides, but their real issue is romantic in nature. At the beginning of the film, Jack tells Oliver about seeing a woman on the subway who he was crazy about after meeting her at a party, but she never called him back despite his multiple tries. “That’s the most depressing story I’ve ever heard in my life,” Oliver says. But it’s going to get worse. Oliver, meanwhile, is head over heels for his girlfriend, Violet (Paulina Singer, “The Wilde Wedding”). She’ll be stopping by the house that night so they can go out — and she turns out to be the object of Jack’s crush.

There are plenty of “oof!” moments in “Stella’s Last Weekend,” such as when Oliver says to Violet, “Jack saw this girl today that he was in love with, and she never called him back.” To his credit, though, Jack talks to Violet whenever he gets the chance, trying to figure out why he didn’t hear from her after what he thought was a true connection. The red light turned out to be a false rumor about Jack having sex with one of the dancers in Violet’s ballet company. Once he disproves it, she admits that she had feelings, too.

Will-they-or-won’t-they isn’t as much of an issue here as whether the relationship between the brothers will get strained — and if Oliver will ever find out the truth. Jack confesses to his mother that he kissed Violet the night he tags along on her and Oliver’s date, and she tells him to stay away from Violet no matter how strongly he feels about her and never to let Oliver know. Valiantly, he follows her advice for as long as he’s able to. But being a rom-com, it’s no spoiler to say the truth will out.

Though Jack and especially Oliver aren’t the most mature dudes around (Oliver, for instance, takes a picture of his ass in public and calls Ron “baldy”), both Wolffs are pretty charismatic and funny. Their rat-a-tat dialogue seems largely improvised (either that or Draper is particularly adept at teen humor) and undoubtedly reflective of a warm sibling relationship.

Singer is sweet and guileless, and though her Violet has a fun connection with Oliver, there’s real chemistry between her and Jack. Draper is likewise affable as the cool mom, and Sandow cringeworthy as a guy who threatens to kick Oliver’s “keister.”

Except for a couple of instances of unfortunate and blurred slo-mo, Draper directs without flourish, allowing the acting to take center stage. You may be surprised to see an inordinate number of female names listed among the top crew’s credits: “Stella’s Last Weekend” may be a film about brotherly love, but behind the scenes, Draper made sure to put women first.