The ‘See You When I See You’ Team on the Joy of Making Films — Even with Tragic Subject Matter

Jay Duplass has been a staple of Sundance and the larger independent film industry for decades, but he spent most of the 2010s and early 2020s taking a break from directing films. Though he stayed busy with acting and TV projects, 2025 saw him return to directing with “The Baltimorons.” He quickly followed that with “See You When I See You,” his bittersweet adaptation of Adam Cayton-Holland’s memoir “Tragedy Plus Time,” starring David Duchovony and Cooper Raiff.

Ahead of the film’s Sundance premiere, Duplass, Cayton-Holland, Duchovony, and Raiff visited the IndieWire Studio, presented by Dropbox, to discuss the film’s journey to the screen.

“I said in a lot of interviews that I miss the movies from the ‘80s, the Jim Brooks and Rob Reiner movies that make you laugh and cry,” Duplass said. “Then this script came along and it was that kind of thing.”

The emotional script, which was also written by Cayton-Holland, was the writer’s attempt to find the humor and heart in an unimaginable personal tragedy.

“It’s a book I wrote in 2018 with the whole story that takes place in this movie, losing my little sister to suicide and how that affected the family,” Cayton-Holland said.  

The film hails from executive producers Kumail Nanjiani and Emily V. Gordon, who adapted their own personal tragedy into the acclaimed film “The Big Sick.” They gave Cayton-Holland a key piece of advice: don’t use your own name in the script. Cayton-Holland explained that changing names gave him the freedom to occasionally veer away from the facts and take creative license to tell his family’s story in a more authentic way.

“It’s a really hard, personal story, obviously I care deeply about how it’s depicted in any form,” he said. “But it certainly helped me to think ‘This is a movie, this is a different thing. We’re here to make the best piece of art we can make to communicate this true message. So it really freed me up to view them as characters and take them where the story needed to go” 

After “The Baltimorons” and “See You When I See You,” Duplass is now firmly back in the world of independent filmmaking. The director explained that despite all of the other successes he has enjoyed, there is still nothing that brings him as much joy as filmmaking.

“I grew up watching movies and had these transformative, emotional experiences inside movie theaters. It’s what I’ve always loved and always wanted to do,” he said. “A lot of things distracted me from that for a while, and for good reason: acting and making TV and things like pandemics. But there was a certain point in time when I realized that telling original stories is what I love the most. It took me quite a while to get back to it, but it is the thing that I love the most.” 

Watch our complete conversation with the “See You When I See You” team above.

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