Movies Like Dear Leo

If you liked Dear Leo (2020), a movie directed by Emma Rappold, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Secret Admirer (1985)
★ 6.7/10
An anonymous love letter left in Michael Ryan's locker on the last day of school wreaks havoc on his life and the lives of everyone who comes in contact with it.
2
Mr. Deeds (2002)
★ 5.9/10
When Longfellow Deeds, a small-town pizzeria owner and poet, inherits $40 billion from his deceased uncle, he quickly begins rolling in a different kind of dough. Moving to the big city, Deeds finds himself besieged by…
3
St. Elmo's Fire (1985)
★ 6.1/10
Reluctant to let go of college life, a close-knit team of seven friends--irresponsible saxophone player Billy, young Republican Alec, his girlfriend Leslie, struggling journalist Kevin, drama queen Jules, lovesick…
4
Mr. Church (2016)
★ 7.4/10
A unique friendship develops when a little girl and her dying mother inherit a cook - Mr. Church. What begins as an arrangement that should only last six months, instead spans fifteen years.
5
Laggies (2014)
★ 6.1/10
Overeducated and underemployed, 28 year old Megan is in the throes of a quarterlife crisis. Squarely into adulthood with no career prospects, no particular motivation to think about her future and no one to relate to…
6
Moonwalkers (2015)
★ 6.1/10
What if Apollo 11 never actually made it? What if, in reality, Stanley Kubrick secretly shot the famous images of the moon landing in a studio, working for the US administration? This is the premise of a totally…
7
Little Italy (2018)
★ 6.6/10
Former childhood pals Leo and Nikki are attracted to each other as adults—but will their feuding parents' rival pizzerias put a chill on their sizzling romance?
8
How to Date Billy Walsh (2024)
★ 6.4/10
Archie has been in love with his best friend Amelia for as long as he can remember. Just when he builds up the courage to declare his feelings, she falls head over heels for Billy Walsh, a new American transfer student.
9
Bob Trevino Likes It (2025)
★ 7.4/10
Lily Trevino unexpectedly befriends an online stranger who shares her self-centered father’s name. This new Bob Trevino’s support could transform her life.
10
Roommates (2026)
★ 6.4/10
When shy college freshman Devon asks cool-girl Celeste to be her roommate, a blossoming friendship quickly spirals into a war of passive aggression.
11
Memory (2023)
★ 7/10
Sylvia is a social worker who leads a simple and structured life: her daughter, her job, her AA meetings. This is blown open when Saul follows her home from their high school reunion. Their surprise encounter will…
12
Fist Fight (2017)
★ 6/10
When one school teacher gets the other fired, he is challenged to an after-school fight.
13
Think Like a Man (2012)
★ 6.8/10
The balance of power in four couples’ relationships is upset when the women start using the advice in Steve Harvey’s book, Act Like A Lady, Think Like A Man, to get more of what they want from their men. When the men…
14
To All the Boys I've Loved Before (2018)
★ 7.6/10
Lara Jean's love life goes from imaginary to out of control when her secret letters to every boy she's ever fallen for are mysteriously mailed out.
15
Letters to Juliet (2010)
★ 7/10
An American girl on vacation in Italy finds an unanswered "letter to Juliet" -- one of thousands of missives left at the fictional lover's Verona courtyard, which are typically answered by the "secretaries of Juliet"…
16
Can You Keep a Secret? (2019)
★ 6.3/10
Emma Corrigan, a girl with a few secrets, thinks she’s about to die on a turbulent plane ride. She spills them all to the handsome stranger sitting next to her. At least, she thought he was a stranger. But then, her…
17
Roxanne (1987)
★ 6.4/10
In this modern take on Edmond Rostand's classic play "Cyrano de Bergerac," C. D. Bales is the witty, intelligent, and brave fire chief of a small Pacific Northwest town who, due to the size of his enormous nose…
18
Dead Poets Society (1989)
★ 8.3/10
At an elite, old-fashioned boarding school in New England, a passionate English teacher inspires his students to rebel against convention and seize the potential of every day, courting the disdain of the stern…
19
The Vow (2012)
★ 7.2/10
Happy young married couple Paige and Leo are, well, happy. Then a car accident puts Paige into a life-threatening coma. Upon awakening she has lost the previous five years of memories, including those of her beloved…
20
The Tender Bar (2021)
★ 6.5/10
JR is a fatherless boy growing up in the glow of a bar where the bartender, his Uncle Charlie, is the sharpest and most colorful of an assortment of quirky and demonstrative father figures. As the boy’s determined…