Movies Like Deb & Sisi

If you liked Deb & Sisi (2008), a movie directed by Mark Kenneth Woods, 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
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…
2
Voicemails for Isabelle (2026)
★ 8.3/10
A young woman's hilariously confessional voicemails to her late sister are unknowingly redirected to a stranger, who begins to fall in love from afar.
3
One Night Only (2026)
★ 6.4/10
Two love-starved strangers crash into each other on the one night of the year when single people are allowed to have sex.
4
Just Before I Go (2015)
★ 6.4/10
Ted Morgan has been treading water for most of his life. After his wife leaves him, Ted realizes he has nothing left to live for. Summoning the courage for one last act, Ted decides to go home and face the people he…
5
Players (2024)
★ 6.1/10
New York sportswriter Mack has spent years devising successful hook-up "plays" with her friends, but when she unexpectedly falls for one of her targets, she must learn what it takes to go from simply scoring to playing…
6
¿Quieres ser mi hijo? (2023)
★ 8.4/10
Lu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship with a young womanizer.
7
There's Something About Mary (1998)
★ 6.6/10
For Ted, prom night went about as bad as it’s possible for any night to go. Thirteen years later, he finally gets another chance with his old prom date, only to run up against other suitors including the sleazy…
8
Girl, Interrupted (1999)
★ 7.6/10
Set in the changing world of the late 1960s, Susanna Kaysen's prescribed "short rest" from a psychiatrist she had met only once becomes a strange, unknown journey into Alice's Wonderland, where she struggles with the…
9
Doing Life (2026)
★ 7.8/10
A single mother and an incarcerated man forge an unlikely bond through heartfelt letters, unlocking a door to redemption, hope and love against all odds.
10
Bridget Jones: Mad About the Boy (2025)
★ 6.3/10
Bridget Jones navigates life as a widow and single mum with the help of her family, friends, and former lover, Daniel. Back to work and on the apps, she's pursued by a younger man and maybe – just maybe – her son's…
11
One Flew Over the Cuckoo's Nest (1975)
★ 8.4/10
A petty criminal fakes insanity to serve his sentence in a mental ward rather than prison. He soon finds himself as a leader to the other patients—and an enemy to the cruel, domineering nurse who runs the ward.
12
He's Just Not That Into You (2009)
★ 6.6/10
Remember that really cute girl/guy who said they'd call – and didn't? Maybe they lost your number. Maybe they're in the hospital. Maybe they're awed by your looks, brains or success. Or maybe... They're just not that…
13
Alfie (2004)
★ 5.9/10
A tale of a philosophical womanizer who is forced to question his seemingly carefree existence.
14
Someone Great (2019)
★ 6.4/10
An aspiring music journalist lands her dream job and is about to move to San Francisco when her boyfriend of nine years decides to call it quits. To nurse her broken heart, she and her two best friends spend one…
15
A Nice Girl Like You (2020)
★ 5.8/10
Lucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her on a whirlwind and surprising journey…
16
Someone Like You... (2001)
★ 6/10
Jane Goodale has everything going for her. She's a producer on a popular daytime talk show, and is in a hot romance with the show's dashing executive producer Ray. But when the relationship goes terribly awry, Jane…
17
How to Date Billy Walsh (2024)
★ 6.4/10
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.
18
Desperados (2020)
★ 6/10
A panicked young woman and her two best friends fly to Mexico to delete a ranting email she sent to her new boyfriend. On arrival, they run into her former beau, who soon gets caught up in their frantic scheme.
19
Trust (1990)
★ 6.8/10
After being thrown away from home, pregnant high school dropout Maria meets Matthew, a highly educated and extremely moody electronics repairman. The two begin an unusual romance built on their sense of mutual…
20
Before I Fall (2017)
★ 7/10
Samantha Kingston has everything. Then, everything changes. After one fateful night, she wakes up with no future at all. Trapped into reliving the same day over and over, she begins to question just how perfect her…