
Dear Leo 2020
Dear Leo (2020) offers a tender, coming-of-age journey framed through an unexpected lens—letters penned by a middle-school boy to his older cousin.
Director: Emma Rappold
Cast

Frequently Asked Questions
What is Dear Leo (2020) about?
Dear Leo (2020) follows Annie Duncan as she embarks on her freshman year of college, seen through the eyes of her middle-school cousin Leo, who writes her letters. These heartfelt missives capture Annie's struggles and triumphs as she navigates new relationships, academic pressures, and self-discovery. It's a touching exploration of family bonds and the unfiltered perspective of youth.
Who directed Dear Leo?
Dear Leo was directed by Emma Rappold, bringing a delicate balance of realism and emotion to the story.
Who stars in Dear Leo?
The film stars Jill Young, Caroline Beagles, Alexandra Intrator, Lauren Weik, and Fazia Rizvi, with Austin Hille rounding out the cast.
Is Dear Leo (2020) worth watching?
Dear Leo (2020) is a charming, low-key gem that offers a fresh take on the coming-of-age genre. While it's not a mainstream hit, its intimate storytelling and emotional depth make it a rewarding watch for fans of character-driven dramas who appreciate understated storytelling.
How long is Dear Leo?
Dear Leo runs for 93 minutes.
About Dear Leo (2020) — Letters that turn a cousin's college journey into a heartfelt coming-of-age story
Dear Leo (2020) offers a tender, coming-of-age journey framed through an unexpected lens—letters penned by a middle-school boy to his older cousin. Through Leo's eyes, we witness Annie Duncan navigate the exhilarating yet daunting transition from high school to college, capturing the raw emotions of uncertainty, growth, and connection. Directed by Emma Rappold, this intimate character study blends humor and heartache, painting a vivid portrait of adolescence with authenticity and warmth.
Set against the backdrop of early adulthood, the film explores themes of family, friendship, and the unspoken bonds that shape us. Rappold's nuanced direction and the ensemble cast bring depth to Annie's story, making Dear Leo (2020) a poignant reflection on the moments that define us before we even realize they're happening.