Movies Like Leo's Love(s)

If you liked Leo's Love(s) (2012), a movie directed by Alan Weischedel, 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
Playing It Cool (2014)
★ 5.9/10
A young man meets and instantly falls in love with an engaged woman.
2
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?
3
Zack and Miri Make a Porno (2008)
★ 6.3/10
Lifelong platonic friends Zack and Miri look to solve their respective cash-flow problems by making an adult film together. As the cameras roll, however, the duo begin to sense that they may have more feelings for each…
4
That Touch of Mink (1962)
★ 6.5/10
Cathy Timberlake is en route to a job interview when a car transporting businessman Philip Shayne covers her in mud. He sends his assistant, Roger, to apologize, but upon meeting Cathy, Roger knows that she would be a…
5
How to Be Single (2016)
★ 6.3/10
New York City is full of lonely hearts seeking the right match, and what Alice, Robin, Lucy, Meg, Tom and David all have in common is the need to learn how to be single in a world filled with ever-evolving definitions…
6
50 First Dates (2004)
★ 6.9/10
Henry is a player skilled at seducing women. But when this veterinarian meets Lucy, a girl with a quirky problem when it comes to total recall, he realizes it's possible to fall in love all over again…and again, and…
7
One Night Only (2026)
★ 6.4/10
Two love-starved strangers crash into each other on the one night of the year when single people are allowed to have sex.
8
About Last Night (2014)
★ 6/10
Bernie and Joan are two fiery flirters who are passionate about everything from hookups to breakups and each other. When he sets up his best friend, Danny, with her roommate, Debbie, the sparks soon fly as they try to…
9
Someone Like You... (2001)
★ 6/10
Jane Goodale has everything going for her. She's a producer on a popular daytime talk show, and is in a hot romance with the show's dashing executive producer Ray. But when the relationship goes terribly awry, Jane…
10
My Sassy Girl (2008)
★ 6.8/10
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
11
The Last Letter from Your Lover (2021)
★ 7.3/10
A young journalist in London becomes obsessed with a series of letters she discovers that recounts an intense star-crossed love affair from the 1960s.
12
Bros (2022)
★ 6.6/10
Two gay men are possibly, probably, stumbling towards love. Maybe. They're both very busy.
13
The Woman in Red (1984)
★ 6.3/10
When a happily married family man, who would never consider an affair, meets a beautiful woman in red, he is totally infatuated and desperate to make her acquaintance. However, as he tries out various schemes to sneak…
14
All Over the Guy (2001)
★ 5.9/10
A contemporary romantic comedy exploring the unlikely pairing of two 20-somethings thrown together by their respective best friends in hopes of igniting their own romance.
15
Alfie (2004)
★ 5.9/10
A tale of a philosophical womanizer who is forced to question his seemingly carefree existence.
16
The Lonely Guy (1984)
★ 6.2/10
A writer for a greeting card company learns the true meaning of loneliness when he comes home to find his girlfriend in bed with another man.
17
She's Funny That Way (2015)
★ 5.9/10
On the set of a playwright's new project, a love triangle forms between his wife, her ex-lover, and the call girl-turned-actress cast in the production.
18
Below Her Mouth (2017)
★ 6.8/10
An unexpected affair quickly escalates into a heart-stopping reality for two women whose passionate connection changes their lives forever.
19
French Girl (2024)
★ 6.2/10
Sweet Gordon, an affable English teacher in Brooklyn, has beaten the odds; a French Girl has fallen in love with him and he’s fallen even harder back. But their future is thrown into limbo when she interviews for an…
20
Manhattan (1979)
★ 7.7/10
Manhattan explores how the life of a middle-aged television writer dating a teenage girl is further complicated when he falls in love with his best friend's mistress.