Movies Like When Harry Met Sally...

If you liked When Harry Met Sally... (1989), a comedy and romance movie directed by Rob Reiner, 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
200 Cigarettes (1999)
★ 5.8/10Also comedy and drama
In 1981 New York City, a collection of twentysomethings try to cope with relationships, loneliness, desire and their individual neuroses on New Years Eve.
2
Something Borrowed (2011)
★ 6.2/10Also comedy and drama
Though Rachel is a successful attorney and a loyal, generous friend, she is still single. After one drink too many at her 30th-birthday celebration, Rachel unexpectedly falls into bed with her longtime crush, Dex…
3
The Apartment (1960)
★ 8.2/10Also comedy and drama
Bud Baxter is a minor clerk in a huge New York insurance company, until he discovers a quick way to climb the corporate ladder. He lends out his apartment to the executives as a place to take their mistresses. Although…
4
Love, Rosie (2014)
★ 7.8/10Also romance and drama
Since the moment they met at age 5, Rosie and Alex have been best friends, facing the highs and lows of growing up side by side. A fleeting shared moment, one missed opportunity, and the decisions that follow send…
5
Book Club (2018)
★ 6.2/10Also romance and comedy
Four lifelong friends decide that their lives could change by becoming nasty and reading Fifty Shades of Grey in their monthly book club to get inspiration on how to handle sexual pleasure at an elderly age.
6
New York, I Love You (2008)
★ 6/10Also comedy and drama
New York, I Love You delves into the intimate lives of New Yorkers as they grapple with, delight in and search for love. Journey from the Diamond District in the heart of Manhattan, through Chinatown and the Upper East…
7
Something from Tiffany's (2022)
★ 6.7/10Also romance and comedy
One woman's life is forever changed by an engagement ring meant for someone else.
8
The Hating Game (2021)
★ 7.3/10Also drama and comedy
Resolving to achieve professional success without compromising her ethics, Lucy embarks on a ruthless game of one-upmanship against cold and efficient nemesis Joshua, a rivalry that is complicated by her growing…
9
Café Society (2016)
★ 6.4/10Also comedy and drama
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.
10
Paper Man (2009)
★ 6.3/10Also comedy and drama
A coming-of-middle-age comedy that chronicles the unlikely friendship between failed author Richard Dunne and a Long Island teen who teaches him a thing or two about growing up, all under the disapproving eye of his…
11
Bridget Jones: Mad About the Boy (2025)
★ 6.3/10Also romance and comedy
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…
12
The Wrong Paris (2025)
★ 6.7/10Also romance and comedy
Dawn thinks she's joining a dating show in Paris, France, only to land in Paris, Texas. She has an exit plan — until sparks fly with the cowboy bachelor.
13
Carol (2015)
★ 7.5/10Also romance and drama
In 1950s New York, a department-store clerk who dreams of a better life falls for an older, married woman.
14
My Dinner with Andre (1981)
★ 7.5/10Also drama and comedy
Wally, a struggling playwright and actor, reluctantly agrees to catch up with his old friend Andre, a theater director who disappeared several years prior in order to travel the world. Meeting at a posh Manhattan…
15
Shortcomings (2023)
★ 6.1/10Also comedy and drama
When his girlfriend leaves for New York City on a 3-month-long internship, a strongly opinionated Berkeley arthouse movie theater manager begins exploring life as a bachelor.
16
Always Be My Maybe (2019)
★ 6.6/10Also romance and comedy
Reunited after 15 years, famous chef Sasha and hometown musician Marcus feel the old sparks of attraction, but struggle to adapt to each other's worlds.
17
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…
18
One Day (2011)
★ 7.4/10Also drama and romance
After spending the night together on the eve of their college graduation, Dexter and Emma are shown each year on the same date to see where they are in their lives. They are sometimes together, and sometimes not.
19
Annie Hall (1977)
★ 7.7/10Also comedy and drama
New York comedian Alvy Singer falls in love with the ditsy Annie Hall.
20
12 Dates of Christmas (2011)
★ 6.1/10Also romance and comedy
In an attempt to win back her ex-boyfriend Jack on Christmas Eve, Kate ends up ruining her blind date with Miles, a handsome guy she's been set up with. In a strange twist of fate, Kate is magically given the chance to…