Greenhill, HP grads collaborate on comedy set in Dallas but filmed in Missouri
Iliza Shlesinger recently revisited an email she wrote to herself back in 2018, just before she got married, about living with regrets from her high school days.
Almost 25 years after she graduated from the Greenhill School, the comedian’s personal sense of nostalgia resonates throughout Chasing Summer, a throwback saga about arrested development and reliving adolescent awkwardness.
The heartfelt film is a passion project that Shlesinger has been working on for several years, and it all traces back to that internal correspondence.
“As an artist and a person, it felt like closing a chapter in my life. In your mid-30s is when it starts to get different,” Shlesinger said following the film’s world premiere at the recent Sundance Film Festival in Utah.
“All of the trappings of youth, whether it was a summer crush, or a random job, or getting to go home and still be a brat in your parents’ house — when you start to get older and you get married, you kind of close the door on that stuff,” she said. “In saying goodbye to that, I was also saying goodbye to a lot of my favorite summers, and just the comfort and excitement that has to do with youth and being home.”
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In the film, which is seeking distribution, Shlesinger plays an international relief worker who retreats home to the suburbs after being dumped. That forces her to navigate a dysfunctional family and confront some past baggage, including a run-in with her ex-boyfriend (Tom Welling). Then a younger guy (Garrett Wareing) causes Jamie to wonder if she had it all wrong.
A producer sent Shlesinger’s screenplay to filmmaker Josephine Decker, a Highland Park graduate best known for her offbeat 2020 literary biopic Shirley.
With the start of production looming, Decker didn’t have much time to decide whether it was the right fit. Enter her partner, filmmaker Malik Vitthal, who added some perspective — and a hunch.
“He was like, ‘I saw Iliza perform live one and a half weeks after she gave birth. She’s electric. You have to say yes. You’re going to make something special together,’” Decker recalled.
“I had been really wanting to make a comedy,” she said. “I got connected to the script. I fell in love with the idea of doing something in my hometown that felt so resonant to my own experience.”
Both women agreed that authenticity was essential — including visual references to Whataburger and Buc-ee’s — although production took place last year in St. Louis for tax-incentive reasons. Still, it brought back memories.
“We were very specific. There is something so ephemeral about a summer at home,” Shlesinger said. “I needed people to feel this, even if they’re not from Texas.”
