Movies Like You Will Meet a Tall Dark Stranger

If you liked You Will Meet a Tall Dark Stranger (2010), a comedy and drama movie directed by Woody Allen, 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
Chéri (2009)
★ 6.1/10Also drama and comedy
The son of a courtesan retreats into a fantasy world after being forced to end his relationship with the older woman who educated him in the ways of love.
2
Sidewalks of New York (2001)
★ 6.1/10Also comedy and drama
The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives…
3
He Said, She Said (1991)
★ 5.9/10Also comedy and drama
Womanising, right-wing Dan Hanson and quiet, liberal Lorie Bryer work for the Baltimore Sun. Rivals for the job of new writer of a vacant column, the paper ends up instead printing their very different opinions…
4
A California Christmas (2020)
★ 6.4/10Also comedy and romance
With his carefree lifestyle on the line, a wealthy charmer poses as a ranch hand to get a hardworking farmer to sell her family’s land before Christmas.
5
The Baltimorons (2025)
★ 6.3/10Also comedy and drama
A newly sober man's Christmas Eve dental emergency leads to an unexpected romance with his older dentist as they explore Baltimore together.
6
Peace, Love & Misunderstanding (2011)
★ 5.8/10Also comedy and drama
A conservative lawyer named Diane takes her two teenage children Jake and Zoe to meet their estranged, hippie grandmother in Woodstock after her husband asks for a divorce.
7
A California Christmas: City Lights (2021)
★ 6.6/10Also romance and comedy
Follows Callie and Joseph one year after they fell in love, now running a dairy farm and winery, but their romance is threatened when business and family obligations call Joseph back to the city.
8
Which Brings Me to You (2023)
★ 6.3/10Also romance and comedy
Two romantic burnouts, Jane and Will, are immediately drawn to each other at a mutual friend’s wedding. After a disastrous hookup in the coatroom, the two spend the next 24 hours together, trading candid confessions of…
9
Is This Thing On? (2025)
★ 6.6/10Also comedy and drama
As their marriage quietly unravels, Alex faces middle age and an impending divorce, seeking new purpose in the New York comedy scene while Tess confronts the sacrifices she made for their family—forcing them to…
10
Father of the Bride (2022)
★ 6.3/10Also romance and comedy
A father comes to grips with his daughter’s upcoming wedding through the prism of multiple relationships within a big, sprawling Cuban-American family.
11
Happiness for Beginners (2023)
★ 6.2/10Also romance and comedy
At a crossroads after her divorce, a schoolteacher ventures toward a fresh start in life — and love — when she signs up for a grueling group hiking trip.
12
I Met a Girl (2020)
★ 6.4/10Also romance and drama
An aspiring musician struggling with schizophrenia falls for a mysterious woman who may be all in his head. When she suddenly vanishes, he takes off on a cross-country journey across Australia to find her, forcing his…
13
Other People's Money (1991)
★ 6.1/10Also comedy and drama
When a corporate raider threatens a hostile takeover of a 'mom and pop' company, the patriarch of the company enlists the help of his wife's attractive daughter—who is a lawyer—to stop the takeover. However, the raider…
14
The Right Kind of Wrong (2013)
★ 5.9/10Also romance and comedy
A stubborn idealist spies a bride on her way to her wedding and immediately falls in love with her.
15
She's Having a Baby (1988)
★ 5.9/10Also comedy and drama
Jake and Kristy Briggs are newlyweds. Being young, they are perhaps a bit unprepared for the full reality of marriage and all that it (and their parents) expect from them. Do they want babies? Their parents certainly…
16
Jersey Girl (2004)
★ 6.2/10Also comedy and romance
Ollie Trinke is a young, suave music publicist who seems to have it all, with a new wife and a baby on the way. But life deals him a bum hand when he's suddenly faced with single fatherhood, a defunct career and having…
17
Not Easily Broken (2009)
★ 6.3/10Also drama and romance
A car accident and shifting affections test the bond between a married couple.
18
Love in Taipei (2023)
★ 6.8/10Also romance and comedy
A young American woman is sent by her parents to a cultural immersion program in Taipei where she begins a new journey of self-discovery and romance.
19
Danny Deckchair (2003)
★ 6.1/10Also comedy and romance
An unappreciated laborer's patience reaches breaking point when his girlfriend cancels a romantic holiday. Making light of the situation, he decides to tie hundreds of helium balloons to a chair in an outlandish bid to…
20
Catch and Release (2006)
★ 5.9/10Also comedy and drama
For a grieving fiancée, learning to love again requires the help of her late love's three best friends.