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Movies Like Two Weeks to 29

Find movies like Two Weeks to 29 using TMDB similarity plus Movie Rankings community context. Our top current pick is Pretty Woman. 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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Pretty Woman

1990

Vivian is a carefree, streetwise diamond in the rough when she meets sophisticated billionaire Edward in a chance encounter that turns into a week-long business arrangement. But Vivian's energetic spirit challenges Edward's no-nonsense approach to life, and soon they are teaching each other – and falling in love!

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 Cutting Edge

1992

Two former Olympians, one a figure skater and the other a hockey player, pin their hopes of one last shot at Olympic glory on one another. That is, of course, if they can keep from killing each other in the process...

TMDB Recommended

In the Heights

2021

The story of Usnavi, a bodega owner who has mixed feelings about closing his store and retiring to the Dominican Republic or staying in Washington Heights.

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Long Weekend

2021

Bart's chance encounter with the enigmatic Vienna leads to a whirlwind weekend together. The two fall fast and hard, but both carry secrets that could be their undoing or the chance for a fresh start.

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Under the Tuscan Sun

2003

Frances Mayes, a 35-year-old professor and writer from San Francisco, decides to take a tour of Tuscany following a difficult divorce. After impulsively buying a run-down villa in the Italian countryside, she begins to piece her life back together in unexpected ways.

TMDB Recommended

Chasing Papi

2003

Playboy Thomas Fuentes has so far been able to skate by in life on good looks and charm alone. But when his duplicitous relationships with three women -- impassioned waitress Cici, meticulous lawyer Lorena and bored socialite Patricia -- spiral out of control, he suffers a mental breakdown. His doctor recommends that he choose just one girlfriend -- but can he choose in time before they discover his deception?

TMDB Recommended

The Wrong Paris

2025

Dawn thinks she's joining a dating show in Paris, France, only to land in Paris, Texas. She has an exit plan — until sparks fly with the cowboy bachelor.

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Totally F***ed Up

1994

Gay, alienated Los Angeles teens have a hard time as their parents kick them out of their homes, they don’t have money, their lovers cheat, and they are harassed by gay-bashers.

TMDB Recommended

The Game Plan

2007

Bachelor football star Joe Kingman seems to have it all. He is wealthy and carefree, and his team is on the way to capturing a championship. Suddenly, he is tackled by some unexpected news: He has a young daughter, the result of a last fling with his ex-wife. Joe must learn to balance his personal and professional lives with the needs of his child.

TMDB Recommended

The Invitation

2016

Will and his new girlfriend Kira are invited to a dinner with old friends at the house of Will’s ex Eden and her new partner David. Although the evening appears to be relaxed, Will soon gets a creeping suspicion that their charming host David is up to something.

TMDB Recommended

Dream Lover

1994

Not long after they cross paths at an art gallery, architect Ray Reardon and hypnotically sensual Lena are married with children. But as strange incidents occur, Ray begins to realize he may not really know the woman he married.

TMDB Recommended

Killer's Kiss

1955

Davey Gordon, a New York City boxer at the end of his career, falls for dancer Gloria Price. However, their budding relationship is interrupted by Gloria's violent boss, Vincent Rapallo, who has eyes for Gloria. The two decide to skip town, but before they can, Vincent and his thugs abduct Gloria, and Davey is forced to search for her among the most squalid corners of the city, with his enemy hiding in the shadows.

TMDB Recommended

French Girl

2024

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 executive chef position in her hometown of Quebec City. To Gordon’s dismay her future boss also happens to be her former lover, a celebrity Chef with oceanic eyes and a hit TV show. Good luck Gordon.

TMDB Recommended

Hello, Goodbye, and Everything in Between

2022

Clare and Aidan make a pact to break up before college — no regrets, no broken hearts. But will one epic goodbye date offer them a last chance at love?

TMDB Recommended

Moonlight in Vermont

2017

After fast-paced New York City high-end real estate broker Fiona Rangely gets dumped by her boyfriend, she escapes to her family’s quaint Vermont Inn for a few days to slow down and evaluate her life. When her ex-boyfriend Nate shows up at the Inn with a brand new girlfriend, Fiona quickly devises a plan to win him back: pretend the handsome and very laid- back head chef Derek is her new boyfriend! Much to the surprise of Derek --and to Fiona herself-- in pretending to be in love, she realizes that she’s been thrown a curveball: sometimes the best things in life are worth the wait.

TMDB Recommended

The Wedding Year

2019

A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.

TMDB Recommended

Picture This

2025

Single and without a man on the horizon, Pia runs a failing photography studio in London with her best friend Jay. As her sister Sonal prepares for marriage and her mother Laxmi urges her to partner up, a spiritual guru predicts Pia will meet the love of her life among her next five dates. With her family intervening, Pia embarks on a hilarious yet heartfelt quest for love.

What are the best movies like Two Weeks to 29?

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