CAUGHT IN THE MIDDLE OF JUNE is about two siblings at a crossroads. Their journeys are messy, funny, and tender, unfolding over one summer where failure and resilience collide, and where love…romantic, familial, and communal, becomes the way forward.

The film follows Ari Morrison (39, Black), a whimsical but insecure teacher, and his younger sister June (30, Black), a cynical illustrator stalled after heartbreak. When Ari loses his job and hides it from his girlfriend Mia Neale (mid-30s, Afro-Latina), while secretly planning a proposal, and June suffers another crushing rejection of her graphic novel, both are pushed toward reinvention.

At June’s bookstore job, she meets Daniel Butala (30s, South Asian), an earnest romantic who challenges her guardedness. With encouragement from her best friend Luna Lindsay (30s, Black/Asian), who is embracing her aromantic identity, June begins to confront her creative fears. She studies under veteran illustrator Camille Ginatra and slowly rediscovers her artistic voice.

Meanwhile, Ari juggles odd jobs and secrets, convinced he can hold things together until he has the perfect moment to propose. But his lies begin to fray under the weight of community: friends like Régine Ghaheri (30s, French-Persian), a mystical philosopher; Mateo Aguilar (40, Mexican-American), Ari’s loyal best friend; and LaBeth (30s, white), June’s eccentric bookstore manager. Their debates, parties, and rituals become the backbone of the siblings’ lives, offering both comic relief and hard truths.

As the summer unfolds, Ari’s secrecy unravels. A confession at a family cookout forces a break with Mia, and a false alarm school lockdown drives him into a spiral. When Mia reveals she’s leaving her job and moving abroad, Ari must decide whether to follow or fall further into despair.

June’s journey mirrors his in reverse. She risks intimacy with Daniel, confronts betrayal when his wealth comes to light, and nearly relapses into drinking before choosing instead to sit with her grief. Through Camille’s mentorship and her own resolve, she begins self-publishing her work, finding independence as both artist and woman.

With guidance from their mother, Ethyl Morrison, the siblings take charge of their healing. Ari proposes to Mia not with a ring but with an airline ticket, ready to embrace change. June reconciles with Daniel on her own terms, choosing partnership rather than rescue.

The film ends at Mia’s farewell party. Surrounded by friends, June and Ari step into the next chapter with fewer illusions but a deeper faith in love, art, and chosen family.