It was spring break of Cooper Raiff’s sophomore year at Occidental College in Los Angeles, and the Dallas native decided to make a short film. He had a story in his head, about a homesick freshman who begins a tentative relationship with the RA of his dorm. Raiff got a few friends together and shot it in seven days. He put the short on YouTube. Then he decided to take a chance.

A longtime fan of University of Texas at Austin alums and mumblecore kings Jay and Mark Duplass, Raiff tweeted at Jay with a link to the short, daring him to watch it. Raiff didn’t really think he would, so he was surprised when Duplass emailed him back and asked to meet him at a nearby diner. “I thought someone was messing with me who had seen the tweet and saw my email address,” Raiff says. “But I still went to the diner and he was there. I freaked out.” Once he calmed down, he listened to Duplass’s advice on what to cut, what to leave in, and how to submit to festivals.

That short, “Madeline and Cooper,” was the start of a process that culminated in Shithouse, Raiff’s soft-spoken feature comedy that won the Grand Jury Prize at the 2020 SXSW Film Festival and launched his directorial career.

Raiff’s newest film, Cha Cha Real Smooth, is a bittersweet comedy about a bar mitzvah “party starter” (Raiff) and a young mother (Dakota Johnson), which Apple TV+ will release June 17. And he’s starting work on The Trashers, starring David Harbour (Stranger Things) as a mobbed-up Connecticut trash magnate who buys a hockey team. At 25, Raiff is an indie film darling.

His mentor isn’t surprised.

“When I saw Cooper’s homemade movie that he dared me to watch over Twitter, it was messy and looked like hell,” Duplass says by email. “But the heart and the comedy and the vulnerability were all there. I didn’t know that he would be this good of a filmmaker this fast, but I just had an inner feeling that whatever he was going to do would be really special.”

Cha Cha Real Smooth, which premiered at this year’s Sundance Film Festival, relieves any concern about a potential sophomore slump. Raiff plays 22-year-old Andrew, a recent college graduate adrift in the world. Living at home with his mom (Leslie Mann), stepdad (Brad Garrett), and little brother (Evan Assante), Andrew passes his time working at a mall food kiosk called Meat Sticks (lots of corn dogs). Then he ends up at a bat mitzvah, where he finds his strange new calling as a party starter, or hype man, wrangling the celebrants and getting them excited for cheesy dances. This is where he meets Domino (Johnson) and her autistic teenage daughter, Lola (Vanessa Burghardt), both of whom are shunned by the cool kids and adults. Andrew is a fumbler who drinks too much at precisely the wrong times and doesn’t seem certain he wants to grow up, just as Domino, suffused with Johnson’s intense earthiness, is certain she needs stability, for herself and for her daughter.

The three outsiders form a bond, Andrew helping out with Lola and dodging Domino’s fiancé (Raúl Castillo), who is remarkably sanguine about the whole thing. Maybe that’s because Raiff is so achingly vulnerable, his big, dark eyes expressing a need to help others even when his characters can’t get out of their own ways. Raiff exudes curiosity and concern. On-screen, he has a nice-guy persona; he comes across as someone who wants to listen to your problems and maybe share a good cry. (Raiff cries more than once in Cha Cha). You feel the loneliness of his characters in Shithouse and Cha Cha. You might feel the need to tell him it will all be okay or offer him a hug.

Cha Cha Real Smooth, named for the 2000 party song “Cha Cha Slide,” is a sweet-natured coming-of-age film about the people and relationships that help us grow up. Like Shithouse, it feels autobiographical—to which Raiff replies, it is and it isn’t.

“I relate to Andrew a ton,” he says. “I’m much better at starting other people’s parties as opposed to starting my own. But I was never in a spot where I graduated college and then moved back home and had a job at Meat Sticks. There are things about him that are very similar to me, and I have similar feelings when I go home.”

For Raiff, home is North Dallas and the prestigious Greenhill School, which he attended from prekindergarten through high school. “It was a magical bubble, and they taught me that I could extend the bubble wherever I went,” Raiff says. Greenhill was where Raiff fell in love with theater, specifically writing and acting. During his senior year, he created his own screenwriting course with his favorite teacher, Catherine Hopkins. She had him analyze a steady diet of plays, including Sam Shepard’s True West, Lanford Wilson’s Lemon Sky, and Thornton Wilder’s Our Town. He played the Stage Manager in a school production of Our Town his senior year and bawled his eyes out every night after the curtains dropped at the prospect of leaving Greenhill, his own personal Grover’s Corners. He included a speech from the play in Shithouse (“I want you to try and remember what it was like to have been very young. . . .”).

“He’s always been a deeply intuitive, sensitive, human creature,” says Hopkins, who now teaches in Hartford, Connecticut. “He’s seeking what it means to be human. I’ve never encountered a student or a person who is more invested in looking for that. He leads with his heart.”

Before he made his short and met Duplass, Raiff figured he would try to make it the old-fashioned Hollywood way. “Since I was in L.A., I tried to go on auditions and stuff,” he says. “I very quickly realized that going on auditions in L.A. is the bleakest thing you’ll ever know.” So he started writing his own material—first a web series, eventually “Madeline and Cooper,” then Shithouse.

He considered himself an actor and writer but was never much interested in directing. Then cold, hard reality intervened: “I quickly realized that no one wanted to direct my college love story, so I had to do it myself.” He’s still figuring out the visual end of things. “I think that I thought that directing was mostly cool shots, but then I learned that’s why you have a director of photography, and that you don’t need to care as much about that,” Raiff says. “I think cinematographers are always stunned by how little I care about visuals.” What he does have is a voice. Hopkins heard it. So did Duplass. In a business that often inspires cynicism, Raiff remains easy to root for even as he accrues that quality guaranteed to inspire envy in show business: success.