Iliza Shlesinger's Chasing Summer Blends Comedy With Emotional Depth

4 weeks ago 12

Published Mar 25, 2026, 4:31 PM EDT

Iliza Shlesinger's Chasing Summer may be rooted in comedy, but it's not afraid to hit much deeper emotional notes. Shlesinger plays Jamie in the film, who, after losing both her job and boyfriend, retreats to her hometown in Texas, where friends and flings from a fateful high school summer turn her life upside down. The small-town story blends sharp humor with a surprisingly heartfelt core, tapping into nostalgia, growing pains, and the kind of feelings that linger long after the credits roll.

Cassidy Freeman: I think the elephant in the room, Iliza Shlesinger, who we keep talking about, I think she would feel the same way about making this film. Even someone as accomplished and followed as she is — someone whose fan base knits sweaters for her dog — to be able to sort of branch out, and do something really different, from her heart, a love story almost to herself. When we were doing press before, she wrote herself an email in 2000 — I don't know — about what it would be like to make this movie, and then she made it, and now it's getting seen by people ... this movie is special because all of us have movies that we watch over and over again. Not necessarily because we don't know what happens, but because of the way it makes us feel. And there's something about this movie, and the way it makes you feel, especially if you were born between a certain couple of years that we'll leave out of this conversation. It feels so nostalgic and fuzzy; you just want to curl up with it and watch it over and over again because we can all relate to it. And you know, there's this Moby song in it. So I feel like when you get a Moby song in your movie, you have won.

Directed by Josephine Decker, known for directing experimental and immersive psychological dramas, the comedy, which, in addition to Shlesinger and Cassidy Freeman, stars Garrett Wareing, Lola Tung, Aimee Garcia, Tom Welling, and Megan Mullally, marks a shift for the director, who manages to stay true to her roots while telling an all-too-relatable millennial melodrama about coming home.

Aimee Garcia: I just love that she really gave us the space, and Josephine, as they said, was an incredible director, and to just speak on these two, the comedy and the drama's seamless change, is awesome. Yes, Cassidy has some belly-laughing moments where you're just hearing the whole audience laugh, but then she rips your heart out in this particularly emotional scene that takes place on a rooftop, and you're like, "Oh my gosh, Oscars eat your heart out." And then this one, which could have been a one-dimensional hottie, but all of a sudden you're like, "Oh, he represents idealism." He represents how we were when we were young, and the impossible was possible, before you go into adulthood, and you're jaded. And so he represents that, and you're like, "We have to give back to that just because we're adults. We don't have to lose that."

I do think it's so nice to laugh and cringe simultaneously. It's a little naughty, it's fun, it's funny, and it's very refreshing, because it's told from a very unique point of view. She literally is the voice of a generation, that one [Shlesinger]. She travels all over the world, and she speaks to millennial humor, and so I think, for us to just see that in a fictional narrative, it's rare to see. So it's really nice to kind of combine the auteur, Sundance-winning, prestigious director in Josephine, with the very grounded, relatable, no BS, likable, and universally loved Iliza. And you put those two together, and it's like, "Avengers, assemble."

Everything The Chasing Summer Cast Said About The Film's Texas Connection

ScreenRant: Being from Texas and having a film at SXSW has to be a pretty cool moment, too.

Garrett Wareing: Josephine, our director, Iliza, our leading lady, and then our writer — we're all from Texas. And so this movie is a love letter to Texas, to Texans. I mean, if you're privy to the comedy and the film, a lot of it references Texas. You have Whataburger in the film. I mean, you have Texas A&M mentioned as well. I'm a fourth-generation Aggie, so this movie was very close to home. Playing the young man that I always wanted to be, and being opposite Iliza, and such a talented, talented actress as she was, I felt so uplifted by her every day, and the other ladies that I got to work with, and Tom Welling. Our director, Josephine, is a master at what she does; bringing one of her films to life was a dream come true.

Aimee Garcia: And Iliza also wrote it, which I think is worth mentioning. So Texas really is almost like its own character. In the movie, you feel the rollerskating rink, you feel the girls with higher, closer-to-God hair, and perfect, impeccable pedicures and manicures, and the very kind of Texas, put together, beautiful — even to go to the grocery store — kind of friends that she has.

ScreenRant: Give me the rundown of who your characters are in the film.

Cassidy Freeman: Well, I play Marissa. I'm Iliza's character's sister. Iliza and I have been friends for years. We worked together a long time ago, and she called me, and she said, "I wrote this movie, and I wrote this character, and it has to be you. Frankly, I want to play this character. I'm mad that you get to play it." She created this almost tactile character of this woman from 2001 that never changed. The hair, the jeans, the nails, the bedazzling, the tattoos. So many tattoos that are not mine. It was so fun to get to play this character who was a little messy, emotional, and just vibrant. And to get to play with Iliza, too, as her sister in this way. There's a thing between siblings that is indescribable, and to get to play that on screen is really fun.

Garrett Wareing: I play Colby. I play Iliza's love interest in the film, and I can't seem to escape the sexy cowboy trope lately, and I feel very lucky. [Chuckles] I think that he resembles the young, good-hearted American boy that I try and want to be. He kind of envisions this life together with Iliza's character, Jamie, in the film, and dreams of something bigger with her, something out of their town, and something together. I think there's some magic that Iliza captured with this kind of youthful longing for a bigger, more adventurous life together. We get into the heart of that, but also the horniness of that as well. And there's a cool balance that Josephine found with that character.

Aimee Garcia: I play Iliza's friend from high school, and what I think my character does in the narrative is show a person how what you think happened back in high school, and what actually happened, might be two totally different things. So, the girls or the guys that you may have thought didn't like you at all, maybe that was just your perception and your point of view. I just love playing a very put-together Texan woman who obviously has her nails done to go to the grocery store and buy vegetables, and doesn't have a hair out of place, and perfect posture, and is so fun, despite having a crying toddler in her arms. She's like, "Everything's fine. Everything's fine. Everything's totally fine. Everything's fine." Even though she's got three kids and her husband is having a beer, she's trying to get him to come over [and help]. I love that she let me sprinkle in some Spanish too, 'cause Spanish is my first language. I'm like, "Hey, Iliza, is it cool if I yell at my husband in Spanish?" She's like, "Absolutely, have fun."

ScreenRant: What is it about this film that makes it unique to you?

Garrett Wareing: I think the idea of this being a love letter to Texas, I think that there's something that everybody can relate to in this, whether it be the idealism that my character holds, or the chaos that Iliza feels coming home to her parents, and seeing her family in her hometown. This is a fun film for everybody, and I really relate to the heart that it brings. I just did a film called The Long Walk, which a lot of people gravitated towards. It's a really intense film. It's sometimes emotional to watch, and to do something uplifting, exciting, and funny was a good contrast to that. I've gravitated towards the joy that I feel from the audience watching this film.

ScreenRant: We met at Comic-Con for The Long Walk, and I feel like life has maybe changed a lot since then. You mentioned that when you landed, you had fans waiting, asking you about things. Can you just talk a little bit about that?

Garrett Wareing: That's very sweet, Ash. I was just telling you this, Comic-Con was my first step into that world, really, and being able to do that amongst the boys that I shared the Long Walk with was really special, in addition to the folks like you that I met on this adventure, as well. We just won an Independent Spirit Award as an ensemble. Francis [Lawrence], our director, won, and our casting director, Rich Delia, and all us boys won for the ensemble. So, to take what life was like at Comic-Con before The Long Walk came out, and it was right after Ransom Canyon had come out, things have really shifted in a way that — I've been doing this for 12 years, since I was a 12-year-old boy. That dream felt so far away for so long, and suddenly I'm sitting here staring the dream right in the face, and it makes me emotional thinking about the fact that your dreams are valid, and your dreams can come true if you put in a little elbow grease, and you stick with the right folks, and lead with gratitude and kindness always, is kind of what I've learned. The gratitude that pumps through my veins. So, just to be sitting here with y'all — it will never be lost to me that this is rare, and a privilege and very, very cool.

Chasing Summer premiered at SXSW, but does not have a confirmed wide theatrical release date yet.