Movies Like Coulda, Woulda, Shoulda

If you liked Coulda, Woulda, Shoulda (2018), a movie directed by Adam Smith, 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
Dot the I (2003)
★ 6/10
A fiery Spanish woman is about to marry a kind British man when she meets a Brazilian actor who ignites in her a flame of lust she can't ignore.
2
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…
3
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.
4
The Disaster Artist (2017)
★ 7.1/10
An aspiring actor in Hollywood meets an enigmatic stranger by the name of Tommy Wiseau, the meeting leads the actor down a path nobody could have predicted; creating the worst movie ever made.
5
The Edge of Love (2008)
★ 6.2/10
When the Welsh poet Dylan Thomas and his flirtatious wife Caitlin sweep into war-torn London, the last thing they expect is to bump into Dylan's childhood sweetheart Vera. Despite her joy at seeing Dylan after so many…
6
Looking: The Movie (2016)
★ 7.1/10
Patrick returns to San Francisco for the first time in almost a year to celebrate a momentous event with his old friends. In the process, he must face the unresolved relationships he left behind and make difficult…
7
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…
8
Café Society (2016)
★ 6.4/10
The story of a young man who arrives in Hollywood during the 1930s hoping to work in the film industry, falls in love, and finds himself swept up in the vibrant café society that defined the spirit of the age.
9
Something Borrowed (2011)
★ 6.2/10
Though Rachel is a successful attorney and a loyal, generous friend, she is still single. After one drink too many at her 30th-birthday celebration, Rachel unexpectedly falls into bed with her longtime crush, Dex…
10
Yoh! Bestie (2026)
★ 6.3/10
Thando is perpetually unlucky in love, but when her bestie returns from his travels with a fiancée in tow, she's forced to face a new emotion — jealousy.
11
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.
12
Playing It Cool (2014)
★ 5.9/10
A young man meets and instantly falls in love with an engaged woman.
13
Relationship Goals (2026)
★ 6.4/10
When TV producer Leah Caldwell aims to become the first woman running New York's top morning show, her ex competes for the same role. Leah stays focused on her career, until chemistry with her ex challenges her…
14
If Beale Street Could Talk (2018)
★ 6.9/10
After her fiance is falsely imprisoned, a pregnant African-American woman sets out to clear his name and prove his innocence.
15
Sweet Home Alabama (2002)
★ 6.4/10
New York fashion designer Melanie Carmichael suddenly finds herself engaged to the city's most eligible bachelor. But her past holds many secrets—including Jake, the redneck husband she married in high school, who…
16
Brooklyn (2015)
★ 7.3/10
In 1950s Ireland and New York, young Eilis Lacey has to choose between two men and two countries.
17
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.
18
The Drama (2026)
★ 6.9/10
A happily engaged couple is put to the test when an unexpected turn sends their wedding week off the rails.
19
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…
20
This Time Next Year (2024)
★ 6.1/10
Minnie and Quinn were both born in London on New Year’s Day, in the same hospital, one minute apart. Thirty years later — and very different people — they find themselves thrown together again in the same city on New…