Movies like Two Weeks to 29 (2020)
The best movies like Two Weeks to 29 (2020) are Playing It Cool (2014), Chasing Papi (2003) and Killer's Kiss (1955). If Two Weeks to 29 hooked you, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedPretty Woman (1990)7.4/10 from 9,303 votes
- NewestYoh! Bestie (2026)Released 2026
Playing 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 thisChasing 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?
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisKiller'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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe 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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisSeriously Single (2020)
While her free-living bestie urges her to embrace singlehood, a commitment-craving social media expert can't stop following the life of a former love.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisFlesh and the Devil (1926)
When lifelong best friends Leo and Ulrich return home after completing their military training, Leo meets the stunning Felicitas at a railway station and is mesmerized by her beauty. A scandal follows, for which Leo is sent away. Returning home three years later, he discovers that much has changed.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisCrossing Delancey (1988)
Thirty-something Isabelle spends her time going from her tiny, solitary West Side apartment to that of her grandmother on the Lower East Side. While her grandmother plots to find her a romantic match, Isabelle is courted by a married, worldly author, Anton, yet can't seem to shake the down-to-earth appeal of Sam, a pickle vendor.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisRomance & Cigarettes (2006)
Ironworker Nick lives with his wife, Kitty, and three daughters. When he meets a significantly younger woman, Tula, he starts an affair with her, much to the chagrin of his wife, and his life is thrown into upheaval. Kitty kicks Nick out of the house, and he is forced to make some difficult decisions.
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 thisIn 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.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisWhat's Love Got to Do with It? (2023)
Two childhood friends now in their thirties must decide whether to follow their heads or their hearts once the man decides to follow his parents' advice and enter into an arranged marriage in Pakistan.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe 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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisDream 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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisPretty 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!
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisPicture 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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe 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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisYour Place or Mine (2023)
When best friends and total opposites Debbie and Peter swap homes for a week, they get a peek into each other's lives that could open the door to love.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisHello, 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?
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Other (2025)
Unable to conceive, a couple seeks to build a family with a young orphan, survivor of tragic childhood. But their act of love turns to horror when they realize the violence in their foster's past has returned to destroy the new family.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe 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.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like this
Like Two Weeks to 29 and something else?
Blend two favourites and we’ll find the films in between.
Frequently asked questions
What are the best movies like Two Weeks to 29?
The closest matches to Two Weeks to 29 are Playing It Cool (2014), Chasing Papi (2003) and Killer's Kiss (1955). Below are 17 more, each with the reason it matches.
What should I watch after Two Weeks to 29?
Start with Playing It Cool (2014), the closest match to Two Weeks to 29.
What is the highest-rated movie like Two Weeks to 29?
Pretty Woman (1990), rated 7.4/10 by 9,303 TMDB users.
What is the newest movie like Two Weeks to 29?
Yoh! Bestie (2026) is the most recent release on this list.
Are there English movies like Two Weeks to 29?
Yes: Playing It Cool (2014), Chasing Papi (2003) and Killer's Kiss (1955).
How are movies similar to Two Weeks to 29 chosen?
First come films that Trakt’s viewers watch alongside Two Weeks to 29, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.