Movies like Coulda, Woulda, Shoulda (2018)
The best movies like Coulda, Woulda, Shoulda (2018) are Dot the I (2003), Indiscreet (1958) and Looking: The Movie (2016). If Coulda, Woulda, Shoulda hooked you, these 20 similar films are what to watch next, and every pick says why it matches.
Coulda, Woulda, Shoulda
Quick picks
- Highest ratedLooking: The Movie (2016)7.1/10 from 250 votes
- NewestOne Night Only (2026)Released 2026
Dot the I (2003)
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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisIndiscreet (1958)
Anna Kalman is an accomplished actress who has given up hope of finding the man of her dreams. While talking about this subject with her sister, in walks Philip Adams and she realizes that this is the charming, smart, and handsome man she has been waiting for.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisLooking: The Movie (2016)
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 choices about what’s important to him.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisHow to Be Single (2016)
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 of love.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisOne Night Only (2026)
Two love-starved strangers crash into each other on the one night of the year when single people are allowed to have sex.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Disaster Artist (2017)
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.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisThe Edge of Love (2008)
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 years, Vera is swept off her feet by a dashing officer, William Killick, and finds herself torn between the open adoration of her new found beau and the wily charms of the exotic Welshman.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Woman in Red (1984)
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 out to meet her, he realizes that adultery is not quite as easy as it looks.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisPersuasion (1995)
In early 19th-century England, dire financial straits reacquaint the aristocratic Anne Elliot with her wealthy ex-fiance Frederick Wentworth. The two must choose between either putting the past behind them or listening to their hearts.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisMy Sassy Girl (2008)
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisCafé Society (2016)
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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisSomething Borrowed (2011)
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 -- who happens to be engaged to her best friend, Darcy. Ramifications of the liaison threaten to destroy the women's lifelong friendship, while Ethan, Rachel's confidant, harbors a potentially explosive secret of his own.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisYoh! Bestie (2026)
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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisPlaying by Heart (1998)
In a vibrant tapestry of love and longing, nine interconnected souls navigate romance and heartbreak in L.A., where passions collide and truths unfold, revealing that the heart's desires often lead us where we least expect.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThis Time Next Year (2024)
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 Year’s Eve.
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 thisPlaying It Cool (2014)
A young man meets and instantly falls in love with an engaged woman.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisRelationship Goals (2026)
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 priorities.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Lonely Guy (1984)
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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisIf Beale Street Could Talk (2018)
After her fiance is falsely imprisoned, a pregnant African-American woman sets out to clear his name and prove his innocence.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like this
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Frequently asked questions
What are the best movies like Coulda, Woulda, Shoulda?
The closest matches to Coulda, Woulda, Shoulda are Dot the I (2003), Indiscreet (1958) and Looking: The Movie (2016). Below are 17 more, each with the reason it matches.
What should I watch after Coulda, Woulda, Shoulda?
Start with Dot the I (2003), the closest match to Coulda, Woulda, Shoulda.
What is the highest-rated movie like Coulda, Woulda, Shoulda?
Looking: The Movie (2016), rated 7.1/10 by 250 TMDB users.
What is the newest movie like Coulda, Woulda, Shoulda?
One Night Only (2026) is the most recent release on this list.
Are there English movies like Coulda, Woulda, Shoulda?
Yes: Dot the I (2003), Indiscreet (1958) and Looking: The Movie (2016).
How are movies similar to Coulda, Woulda, Shoulda chosen?
First come films that Trakt’s viewers watch alongside Coulda, Woulda, Shoulda, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.