Cooper Raiff, what are you doing here?
By Kristy Puchko on April 4, 2026
Last year, Jay Duplass directed the brilliantly funny “Baltimorons,” which starred co-writer Michael Strassner as an improv comedian who finds a new lease on life through an unexpected friendship with an ornery dentist. This year, Duplass offers a sibling film of sorts as his follow-up, adapting stand-up comedian Adam Cayton-Holland’s memoir, “Tragedy Plus Time,” into the drama “See You When I See You.”
Where “The Baltimorons” centered on (and starred) a comedian dealing with suicidal ideation, “See You When I See You” focuses on a family grieving the loss of their sister and daughter to suicide. Cayton-Holland wrote the adapted screenplay for “See You When I See You,” but unlike Strassner, he does not star in the resulting film. Instead, Duplass casts indie ingedude Cooper Raiff (“Cha Cha Real Smooth, Shithouse”) to play the lead of a comedian who can’t cope when confronting the death of his younger sister, Leah (Kaitlyn Dever).
While the supporting cast is made up of compelling performers, including David Duchovny, Lucy Boynton, and Hope Davis, “See You When I See You” is hampered by a leading man who cannot shoulder the emotional weight of this story.
See You When I See You explores a family’s suicide loss.
Two months after Leah’s death by suicide, the Whistler family is cleaning out her apartment. Older sister Emily (Boynton) is determinedly trying to catch the koi fish that her whimsical sibling kept in a pond not approved by the landlord. Their lawyer father Robert (Duchovny) is buttoning up paperwork, while his wife Page (Davis) is rejecting the idea of a funeral for her youngest child. Meanwhile, middle child Aaron (Raiff) is lost in thought looking at an old photo of the whole family.
“See You When I See You” explores a different way of coping with grief through each character. Emily, who has a kid and husband to look after along with her father’s law firm, finds comfort in grounding herself in a task. Robert invests himself in making sure his wife and other children are okay, but can’t rest because they definitely are not. Page is shutting herself off from everything — the pain of this loss, her family’s attention, and even the panic when she discovers a lump in her breast. Aaron is embracing chaos and rejecting therapy.
Aaron’s ghosted a could-be girlfriend. He’s bailing on work at his comedy writing job. He’s falling into memories of his younger sister that warp into nightmare scenarios. For instance, recalling the last night they hung out, he and Leah are bullshitting happily at a bar. But a conversation that once felt mundane now carries a great, horrible importance because it was their last. As she talks, the paneled ceiling of the bar gives away to reveal a ravenous black hole, seeking to suck up anything it can, including Leah. In his distorted memory, Aaron calls out to her, demanding to understand why.
This imagery recurs in “See You When I See You”. It’s effective because, yeah, that’s what grief can feel like, an insatiable sucking hole eager to gobble us up without mercy. These scenes are all the more disturbing because of how nonchalantly Dever plays them. While Raiff shrieks in terror, she is casual when facing her character’s oblivion. This visual and dissonance well reflects the anger Aaron has at his sister, but Raiff himself falls flat in selling the emotion.
Cooper Raiff drags down See You When I See You.
Whether he’s flirting awkwardly with a crush, bickering with his older sister, or cajoling his mother, Aaron’s every move feels like a performance. Raiff’s approach to the material is too broad to blend with the rest of the cast. And perhaps that is intentional, meant to echo how Aaron, as a comedian, is ill-equipped to cope with something so serious. But that approach would only work if Raiff’s performance becomes grounded or nuanced at some point, and it just doesn’t.
His fumbling becomes frustrating as Aaron’s story overtakes the plotline, though his sister’s and his parents’ respective narrative arcs are much more compelling. Page and Robert, who in flashbacks are radiantly in love, can barely be in the same room. He craves her, but her hurt can’t allow her to be vulnerable in conversation or copulation. In quiet moments alone, both Davis and Duchovny silently seethe with heartache that is almost deafening.
They’re good. But Boynton (“The Greatest Hits”) is brilliant and blistering. In the hands of a lesser actress, Emily might come off as obnoxiously bossy or coldly arrogant