Movies like Dear Leo (2020)
The best movies like Dear Leo (2020) are Secret Admirer (1985), Mr. Deeds (2002) and Mr. Church (2016). If Dear Leo hooked you, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedTo All the Boys I've Loved Before (2018)7.6/10 from 8,811 votes
- NewestRoommates (2026)Released 2026
Secret Admirer (1985)
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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisMr. Deeds (2002)
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 opportunists all gunning for their piece of the pie. Babe, a television tabloid reporter, poses as an innocent small-town girl to do an exposé on Deeds.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisMr. Church (2016)
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.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisLaggies (2014)
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, Megan is comfortable lagging a few steps behind - while her friends check off milestones and celebrate their new grown-up status. When her high-school sweetheart proposes, Megan panics and- given an unexpected opportunity to escape for a week - hides out in the home of her new friend, 16-year old Annika and Annika's world-weary single dad Craig.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisSt. Elmo's Fire (1985)
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 waiter Kirby, and Wendy, a social worker with a heart of gold--realise the party is over. And as the burdens of maturity close in on the young dreamers, the complexities of adulthood and the daily struggle of growing up put their sacred friendship to the test. But everyone knows life is not a bed of roses. It won't be easy, but when all is said and done, what will it take for St. Elmo's clique to find its place in the real world?
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisLittle Italy (2018)
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?
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisMoonwalkers (2015)
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 plausible conspiracy theory that takes us to swinging sixties London, where a stubborn CIA agent will never find Kubrick but is forced to team up with a lousy manager of a seedy rock band to develop the biggest con of all time.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisHow to Date Billy Walsh (2024)
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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisRoommates (2026)
When shy college freshman Devon asks cool-girl Celeste to be her roommate, a blossoming friendship quickly spirals into a war of passive aggression.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisMemory (2023)
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 profoundly impact both of them as they open the door to the past.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisBob Trevino Likes It (2025)
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.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisBrave the Dark (2025)
When Mr. Deen discovers one of his students has been living out of his car and thrown into jail, he decides to bail him out. Determined to curb Nate’s self-destructive behavior, Deen quickly discovers a host of dark secrets slowly tearing Nate apart. What began as a good deed becomes a desperate fight to save Nate from his own demons. As Nate spirals deeper into despair, Deen must decide how far he’s willing to go to save a kid on the brink of losing everything—even himself.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThink Like a Man (2012)
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 realize that the women have gotten a hold of their relationship “playbook,” they decide that the best defense is a good offense and come up with a plan to use this information to their advantage.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisIn Good Company (2004)
Dan Foreman is a seasoned advertisement sales executive at a high-ranking publication when a corporate takeover results in him being placed under naive supervisor Carter Duryea, who is half his age. Matters are made worse when Dan's new supervisor becomes romantically involved with his daughter an 18 year-old college student Alex.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisRoxanne (1987)
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, declines to pursue the girl of his dreams, lovely Roxanne Kowalski. Instead, when his shy underling Chris McConnell becomes smitten with Roxanne, C.D. feeds the handsome young man the words of love to win her heart.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisFist Fight (2017)
When one school teacher gets the other fired, he is challenged to an after-school fight.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisTo All the Boys I've Loved Before (2018)
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.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisWork It (2020)
A brilliant but clumsy high school senior vows to get into her late father's alma mater by transforming herself and a misfit squad into dance champions.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisLove in the Time of Cholera (2007)
In Colombia just after the Great War, an old man falls from a ladder; dying, he professes great love for his wife. After the funeral, a man calls on the widow - she dismisses him angrily. Flash back more than 50 years to the day Florentino Ariza, a telegraph boy, falls in love with Fermina Daza, the daughter of a mule trader.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisLetters to Juliet (2010)
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" -- and she goes on a quest to find the lovers referenced in the letter.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like this
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Frequently asked questions
What are the best movies like Dear Leo?
The closest matches to Dear Leo are Secret Admirer (1985), Mr. Deeds (2002) and Mr. Church (2016). Below are 17 more, each with the reason it matches.
What should I watch after Dear Leo?
Start with Secret Admirer (1985), the closest match to Dear Leo.
What is the highest-rated movie like Dear Leo?
To All the Boys I've Loved Before (2018), rated 7.6/10 by 8,811 TMDB users.
What is the newest movie like Dear Leo?
Roommates (2026) is the most recent release on this list.
Are there English movies like Dear Leo?
Yes: Secret Admirer (1985), Mr. Deeds (2002) and Mr. Church (2016).
How are movies similar to Dear Leo chosen?
First come films that Trakt’s viewers watch alongside Dear Leo, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.