Movies Like Two Weeks to 29

If you liked Two Weeks to 29 (2020), a movie directed by Jesús M. Rodriguez, 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
Playing It Cool (2014)
★ 5.9/10
A young man meets and instantly falls in love with an engaged woman.
2
The Invitation (2016)
★ 6.4/10
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…
3
Chasing Papi (2003)
★ 6.7/10
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…
4
Romance & Cigarettes (2006)
★ 6.1/10
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…
5
Killer's Kiss (1955)
★ 6.3/10
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…
6
Seriously Single (2020)
★ 6.8/10
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.
7
Picture This (2025)
★ 6/10
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…
8
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.
9
In the Heights (2021)
★ 7.1/10
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.
10
Flesh and the Devil (1926)
★ 7.2/10
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…
11
Dream Lover (1994)
★ 6.8/10
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…
12
Pretty Woman (1990)
★ 7.4/10
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…
13
The Wrong Paris (2025)
★ 6.7/10
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.
14
The Game Plan (2007)
★ 6.5/10
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…
15
What's Love Got to Do with It? (2023)
★ 6.1/10
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.
16
French Girl (2024)
★ 6.2/10
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…
17
Your Place or Mine (2023)
★ 6.2/10
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.
18
(500) Days of Summer (2009)
★ 7.3/10
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…
19
Stonehearst Asylum (2014)
★ 6.9/10
An Oxford Medical School graduate takes a position at a mental institution and soon becomes obsessed with a female mental patient, but he has no idea of a recent and horrifying staffing change.
20
Under the Tuscan Sun (2003)
★ 6.9/10
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…