Movies Like Free Spirit

If you liked Free Spirit (2019), a movie directed by Francesca Root-Dodson, 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
How to Be Single (2016)
★ 6.3/10
New York City is full of lonely hearts seeking the right match, and what Alice, Robin, Lucy, Meg, Tom and David all have in common is the need to learn how to be single in a world filled with ever-evolving definitions…
2
June and John (2025)
★ 6.1/10
John leads an ordinary life with a monotonous routine. One day John runs into a woman on the subway who is as beautiful as she is mysterious named June. His encounter with her finally leads him to have a goal in his…
3
Wonderstruck (2017)
★ 6.1/10
The story of a young boy in the Midwest is told simultaneously with a tale about a young girl in New York from fifty years ago as they both seek the same mysterious connection.
4
My Sassy Girl (2008)
★ 6.8/10
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
5
The Age of Innocence (1993)
★ 7/10
In 19th century New York high society, a young lawyer falls in love with a woman separated from her husband, while he is engaged to the woman's cousin.
6
Whatever Works (2009)
★ 7.1/10
Whatever Works explores the relationship between a crotchety misanthrope, Boris and a naïve, impressionable young runaway from the south, Melody. When Melody's uptight parents arrive in New York to rescue her, they are…
7
G (2002)
★ 6.6/10
A young Hip Hop star named Summer G falls for a middle to upper class sister while in college. After she rejects him for a fellow social climber, Summer G spends ten years building a Hip Hop empire, then moves to the…
8
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.
9
Two Lovers (2008)
★ 6.9/10
A depressed man moves back in with his parents following a recent heartbreak and finds himself with two women.
10
The Map That Leads to You (2025)
★ 6.7/10
Heather is a young woman traveling Europe with friends before starting her perfectly planned life. A chance meeting with Jack sparks an unexpected romance that leads to deep emotional discovery. As secrets and life…
11
Carlito's Way (1993)
★ 7.8/10
Free after years in prison, Carlito Brigante intends to give up his criminal ways, but it's not long before the ex-con is sucked back into the New York City underworld.
12
The Clock (1945)
★ 7.1/10
A G.I. en route to Europe falls in love during a whirlwind two-day leave in New York City.
13
London (2005)
★ 6/10
London is a drug laden adventure that centers on a party in a New York loft where a young man is trying to win back his ex-girlfriend.
14
The Purple Rose of Cairo (1985)
★ 7.4/10
Cecilia is a waitress in New Jersey, living a dreary life during the Great Depression. Her only escape from her mundane reality is the movie theatre. After losing her job, Cecilia goes to see 'The Purple Rose of Cairo'…
15
A Night at the Roxbury (1998)
★ 6.6/10
Despite being well into adulthood, brothers Doug and Steve Butabi still live at home and work in the flower shop owned by their dad. They exist only to hit on women at discos, though they're routinely unsuccessful…
16
Great Expectations (2012)
★ 6.4/10
Orphan Pip discovers through lawyer Mr. Jaggers that a mysterious benefactor wishes to ensure that he becomes a gentleman. Reunited with his childhood patron, Miss Havisham, and his first love, the beautiful but…
17
The Age of Adaline (2015)
★ 7.5/10
After 29-year-old Adaline recovers from a nearly lethal accident, she inexplicably stops growing older. As the years stretch on and on, Adaline keeps her secret to herself until she meets a man who changes her life.
18
¿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.
19
Hello, Dolly! (1969)
★ 7/10
Dolly Levi is a strong-willed matchmaker who travels to Yonkers, New York in order to see the miserly "well-known unmarried half-a-millionaire" Horace Vandergelder. In doing so, she convinces his niece, his niece's…
20
The True Adventures of Wolfboy (2019)
★ 5.9/10
Follows a young boy who runs away from home in the search of his estranged mother.