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Movies that feel like A Rainy Day in New York (2019)

If you loved A Rainy Day in New York, the closest films we have are Rich in Love (2020), Café Society (2016) and Trainwreck (2015). All three share A Rainy Day in New York's witty and playful feel, which is what we rank on before quality. 5 of the 12 picks below are included with a subscription right now on Netflix and Amazon Prime Video and others, checked against today's data.

Two young people arrive in New York to spend a weekend, but once they arrive they're met with bad weather and a series of adventures.

🍅 46% Rotten Tomatoes6.4 IMDb ↗TMDB ↗dir. Woody Allenwittyplayfulromantictender
Stream it:Prime Video
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If A Rainy Day in New York hit the spot, these will too

Rich in Love poster
Rich in Love
2020 · dir. Bruno Garotti
6romance · comedy

Both keep coming back to the same thing: romance

Working incognito at his rich dad's company to test his own merits, Teto falls for Paula and tells her he grew up poor, a lie that spins out of control.

Café Society poster
Café Society
2016 · dir. Woody Allen
🍅 70%6.6comedy · drama · romance

Both are Woody Allen's work, and they rhyme

The difference: Leans harder into drama than A Rainy Day in New York does

The story of a young man who arrives in Hollywood during the 1930s hoping to work in the film industry, falls in love, and finds himself swept up in the vibrant café society that defined the spirit of the age.

Trainwreck poster
Trainwreck
2015 · dir. Judd Apatow
🍅 84%6.2comedy · romance

Both are built on the same subject: interview

The difference: Reviewed even better

Ever since her father drilled into her head that monogamy isn't realistic, magazine writer Amy has made promiscuity her credo. As much as she enjoys an uninhibited life free of commitment, Amy is really in a rut. While writing a profile about charming and successful sports doctor Aaron Conners, she finds herself actually falling in love for the first time -- and what's more, Aaron seems to really like her too. Amy starts to wonder if it's time to clean up her act and face her fears.

The Purple Rose of Cairo poster
The Purple Rose of Cairo
1985 · dir. Woody Allen
🍅 93%7.6fantasy · comedy · romance

Woody Allen working the same nerve twice

The difference: Sits closer to fantasy than A Rainy Day in New York does

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' in hopes of raising her spirits, where she watches dashing archaeologist Tom Baxter time and again.

Through My Window: Across the Sea poster
Through My Window: Across the Sea
2023 · dir. Marçal Forés
5.2romance · drama · comedy

Common ground: young couple

After a year of long-distance, Raquel and Ares reunite on a steamy beach trip. Faced with fresh flirtations and insecurities, will their love prevail?

How to Be Single poster
How to Be Single
2016 · dir. Christian Ditter
🍅 45%6.1comedy · romance

Both rooted in New York City

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 of love.

Manhattan poster
Manhattan
1979 · dir. Woody Allen
🍅 93%7.8comedy · drama · romance

Witty where it counts, playful underneath

The difference: 40 years apart, and the 1970s show

Manhattan explores how the life of a middle-aged television writer dating a teenage girl is further complicated when he falls in love with his best friend's mistress.

Obvious Child poster
Obvious Child
2014 · dir. Gillian Robespierre
🍅 90%6.7comedy · romance

The same mix in both: romance, then tenderness

An immature, newly unemployed comic must navigate the murky waters of adulthood after her fling with a graduate student results in an unplanned pregnancy.

Set It Up poster
Set It Up
2018 · dir. Claire Scanlon
🍅 92%6.5romance · comedy

Both lean on wit more than on comedy

Two overworked and underpaid assistants come up with a plan to get their bosses off their backs by setting them up with each other.

Lisbela and the Prisoner poster
Lisbela and the Prisoner
2003 · dir. Guel Arraes
7.6comedy · romance

One thread runs through both: romance

Lisbela is a young woman who loves going to the movies. Leléu is a con man, going from town to town selling all sort of things and performing as master of ceremonies for some cheesy numbers, such as the woman who gets transformed into a gorilla. He gets involved with Linaura, a sexy and beautiful woman who happens to be the wife of the most frightening hitman of the place. The hitman finds out his wife's affair and goes after Leléu, who has to leave in a hurry. In another town, he meets and falls instantly in love with Lisbela, who is engaged to Douglas, a hillbilly who tries hard to pass for a cosmopolitan Rio de Janeiro dweller.

Valentine's Day poster
Valentine's Day
2010 · dir. Garry Marshall
🍅 18%5.8comedy · romance

The same preoccupation in both: kiss

Intertwining couples and singles in Los Angeles break-up and make-up based on the pressures and expectations of Valentine's Day.

Isi & Ossi poster
Isi & Ossi
2020 · dir. Oliver Kienle
6.4romance · comedy

Romance built on play, twice over

Isi and Ossi couldn't be any more different: She's a billionaire's daughter from Heidelberg, he's a struggling boxer from the nearby town of Mannheim. But when Isi meets Ossi, the two quickly realize that they can take advantage of one another: She dates the broke boxer to provoke her parents and get them to fund a long-desired chef training in New York. He tries to rip off the rich daughter to finance his first professional boxing match. Their plans soon develop into emotional chaos that challenges everything the two believe to know about money, career and love.

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The best-reviewed films that share A Rainy Day in New York’s defining feeling.