Movies Like Twenty Questions

If you liked Twenty Questions (2009), a movie, 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
Sleuth (1972)
★ 7.7/10
A man who loves games and theatre invites his wife's lover to meet, setting up a battle of wits with potentially deadly results.
2
The Switch (2010)
★ 6.2/10
Kassie is a smart, fun-loving single woman who, despite her neurotic best friend Wally’s objections, decides it’s time to have a baby – even if it means doing it herself… with a little help from a charming sperm donor…
3
Bad Sister (2015)
★ 6.6/10
As a top student at St. Adeline's Catholic Boarding School, Zoe senses that something is not quite right about the school's new nun-- a sense proven to be true when it is revealed the "good' nun is an imposter with a…
4
Brief Encounter (1945)
★ 7.7/10
Returning home from a shopping trip to a nearby town, bored suburban housewife Laura Jesson is thrown by happenstance into an acquaintance with virtuous doctor Alec Harvey. Their casual friendship soon develops during…
5
Solo Mio (2026)
★ 7.5/10
After Matt's dreams of a picturesque Italian wedding are shattered when his fiancée leaves him at the altar, he embarks on his planned honeymoon across Italy alone, immersing himself in the country's vibrant culture…
6
To All the Boys: P.S. I Still Love You (2020)
★ 6.8/10
Lara Jean and Peter have just taken their romance from pretend to officially real when another recipient of one of her love letters enters the picture.
7
The World According to Garp (1982)
★ 6.7/10
A struggling young writer finds his life and work dominated by his unfaithful wife and his radical feminist mother, whose best-selling manifesto turns her into a cultural icon.
8
Me Time (2022)
★ 5.8/10
With his family away, a devoted stay-at-home dad enjoys his first me time in years by joining his hard-partying old friend on a wild birthday adventure.
9
The Secret Life of Bees (2008)
★ 7.5/10
Set in South Carolina in 1964, this is the tale of Lily Owens a 14 year-old girl who is haunted by the memory of her late mother. To escape her lonely life and troubled relationship with her father, Lily flees with…
10
The Lonely Guy (1984)
★ 6.2/10
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.
11
After We Collided (2020)
★ 7.1/10
Tessa finds herself struggling with her complicated relationship with Hardin; she faces a dilemma that could change their lives forever.
12
Nerve (2016)
★ 7/10
Industrious high school senior Vee Delmonico has had it with living life on the sidelines. When pressured by friends to join the popular online game Nerve, Vee decides to sign up for just one dare in what seems like…
13
Ice Road: Vengeance (2025)
★ 6.2/10
Big rig ice road driver Mike McCann travels to Nepal to scatter his late brother’s ashes on Mt. Everest. While on a packed tour bus traversing the deadly 12,000 ft. terrain of the infamous Road to the Sky, McCann and…
14
Eat Pray Love (2010)
★ 6.2/10
A married woman realizes how unhappy her marriage really is, and that her life needs to go in a different direction. After a painful divorce, she takes off on a round-the-world journey to "find herself".
15
Roxanne (1987)
★ 6.4/10
In this modern take on Edmond Rostand's classic play "Cyrano de Bergerac," C. D. Bales is the witty, intelligent, and brave fire chief of a small Pacific Northwest town who, due to the size of his enormous nose…
16
Ice Princess (2005)
★ 6.5/10
With the help of her coach, her mom, and the boy who drives the Zamboni, nothing can stop Casey Carlyle from realizing her dream to be a champion figure skater.
17
Prom Pact (2023)
★ 7.2/10
It's prom season, and high school senior Mandy and her best friend and fellow outsider Ben are surrounded by over-the-top "promposals." Mandy is only focused on getting into her dream school Harvard, but as she starts…
18
Piper (2016)
★ 8.1/10
A mother bird tries to teach her little one how to find food by herself. In the process, she encounters a traumatic experience that she must overcome in order to survive.
19
The Princess Diaries 2: Royal Engagement (2004)
★ 6.7/10
Mia Thermopolis is now a college graduate and on her way to Genovia to take up her duties as princess. Accompanied by her friend Lilly, Mia continues her 'princess lessons', like riding horses side-saddle and archery…
20
The Vow (2012)
★ 7.2/10
Happy young married couple Paige and Leo are, well, happy. Then a car accident puts Paige into a life-threatening coma. Upon awakening she has lost the previous five years of memories, including those of her beloved…