Caught in the Middle of June is a grounded, character-driven romantic comedy about creative reclamation, chosen joy, and the bravery it takes to start anew, told through a distinctly  Black, femme, and nerdy lens.

June Montoya is a 30-year-old illustrator who—after years of rejection, a broken engagement, and artistic burnout—has chosen safety over ambition. She lives quietly in Richmond, Virginia, working at a used bookstore, gaming late into the night, and drowning out her thoughts with curated playlists and background noise. Her days are neat, numbed, and carefully managed. She’s not thriving. She’s hiding. 

That changes when her older brother Ari, a gentle, former lawyer turned robotics coach, asks her to help plan a surprise proposal for his girlfriend, Mia. The proposal will take place during Ari’s own 40th birthday party…which he doesn’t know he’s having. What begins as a simple favor quickly becomes a logistical and emotional minefield of secrets, especially when June learns she’ll be planning it alongside Mia’s cousin Daniel, an earnest, intuitive indie publisher, whose optimism makes June bristle. He’s annoyingly sincere. And yet…impossible to ignore. 

As the pair navigate venue mishaps, floral negotiations, and late-night planning, their dynamic slowly transforms. They bond over comics, music, and shared silences, each revealing pieces of themselves the other doesn’t judge. Their witty banter simmers. In one moment, Daniel coaxes her onto a Brazilian dance floor; in another, she shares a headphone and a song.

The ensemble surrounding June deepens the film’s texture: Ari and Mia’s polyamorous relationship models mutuality and emotional transparency. Luna, June’s asexual veterinarian roommate, keeps her honest. And Camille Ginatra, a legendary comic artist who offers June a chance at mentorship, presents a challenge: if the door to her dreams reopens, will June walk through it?

June’s arc is both romantic and creative. She shows up. Not perfectly, but fully. She turns down Daniel’s offer to work at his publishing company, choosing instead to study with Camille and chart her own creative path. Instead, she gives Daniel something else: a matching set of lucky coins, a small gesture of trust. Of forward motion. Not a finish line. A threshold. June doesn’t leave with a fairytale or a five-year plan. But she does reclaim her voice. She makes peace with what she lost. And lets herself want something more.

Caught in the Middle of June is for the quietly devastated and the almost-ready. It centers late bloomers and those suspended between self-protection and possibility. It’s a story about returning—to risk, to community, to the version of yourself you thought was gone—but maybe wasn’t gone at all. Just waiting.