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Movies Like Coulda, Woulda, Shoulda

Find movies like Coulda, Woulda, Shoulda using TMDB similarity plus Movie Rankings community context. Our top current pick is (500) Days of Summer. Browse 18 related titles with direct links to rankings, cast pages, and matchup data.

These picks blend TMDB similar-title seeds with Movie Rankings community ranking context.

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Recommended If You Liked Coulda, Woulda, Shoulda
TMDB Recommended

(500) Days of Summer

2009

Tom, greeting-card writer and hopeless romantic, is caught completely off-guard when his girlfriend, Summer, suddenly dumps him. He reflects on their 500 days together to try to figure out where their love affair went sour, and in doing so, Tom rediscovers his true passions in life.

TMDB Recommended

The Kissing Booth

2018

When teenager Elle's first kiss leads to a forbidden romance with the hottest boy in high school, she risks her relationship with her best friend.

TMDB Recommended

Looking: 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.

TMDB Recommended

Persuasion

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.

TMDB Recommended

The 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.

TMDB Recommended

The Wedding Date

2005

With the wedding of her younger sister fast approaching, Kat Ellis faces the undesirable prospect of traveling alone to London for the ceremony. While this is bad enough, Jeffrey, the man who left her as they moved closer to marriage, happens to be the groom's best man. Determined to show everyone -- most of all Jeffrey -- that her romantic life is as full and thrilling as ever, Kat hires a charming male escort as her date.

TMDB Recommended

My Sassy Girl

2008

A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.

TMDB Recommended

Indiscreet

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.

TMDB Recommended

Playing 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.

TMDB Recommended

Café 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.

TMDB Recommended

Sweet Home Alabama

2002

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 refuses to divorce her. Bound and determined to end their contentious relationship once and for all, Melanie sneaks back home to Alabama to confront her past.

TMDB Recommended

How 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.

TMDB Recommended

How 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.

TMDB Recommended

The 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.

TMDB Recommended

Something 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.

TMDB Recommended

The 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.

TMDB Recommended

St. 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?

TMDB Recommended

This 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.

What are the best movies like Coulda, Woulda, Shoulda?

(500) Days of Summer is the strongest current recommendation on this page for viewers looking for movies like Coulda, Woulda, Shoulda.

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