Best Romantic Comedies Perfect for Valentine's Day

Publish date: 2024-06-14

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Who doesn’t love the giddy feeling of butterflies in your stomach once you finally sit down and turn on your favorite rom-com?

The beloved movies are known for making a person catch feelings in all the best ways, from witnessing an adorable meet-cute, to waiting in suspense for the highly anticipated first kiss, to hoping that everything works out perfectly in the end. While rom-coms may pull on one’s heartstrings and cause audiences to cry their eyes out, they can also provide iconic comedic moments, making the viewer laugh out loud minutes later.

Though there have been some memorable films released in the 21st century, including The Proposal, Crazy Rich Asians, Love and Basketball and Crazy, Stupid, Love., romantic comedies were notably all the rage in the late ’80s and ’90s, with stars like Meg Ryan, Tom Hanks and Julia Roberts dominating the movie genre. Many of their films, including When Harry Met Sally, Pretty Woman and Sleepless in Seattle, have since become rom-com staples, and are still adored today.

However, the film genre saw a decrease in box office revenue during the mid to late 2010s, especially during the COVID-19 pandemic, according to Statista. But, since 2022, rom-coms have started making a comeback with the help of streaming giants such as Netflix and Prime Video.

Now, there’s no denying that there are hundreds of beloved romantic comedies that deliver all the best feelings, and while this list doesn’t come close to including them all, The Hollywood Reporter has compiled some must-watch rom-coms, perfect for any day of the year, but especially Valentine’s Day, below.

'You’ve Got Mail' (1998)
Tom Hanks and Meg Ryan teamed up for this Nora Ephron-directed rom-com, which follows boutique bookseller Kathleen Kelly and her competitor Joe Fox, the owner of a corporate Foxbooks, as they start an anonymous internet romance, oblivious of each other’s true identity and their competing businesses.
Watch You’ve Got Mail online Buy or rent on Apple TV, Prime Video
'10 Things I Hate About You' (1999)
In the movie starring Heath Ledger and Julia Stiles, high school student Kat Stratford isn’t very social and tries to keep to herself. But her younger sister, Bianca (Larisa Oleynik), is in a predicament because she can’t date until Kate has a boyfriend. So Bianca embarks on a plan to find her older sister a potential love interest, and that’s where mysterious new student Patrick Verona comes in. 10 Things I Hate About You was directed by Gil Junger.
Watch 10 Things I Hate About You online Stream on Hulu; buy or rent on Apple TV, Prime Video
'Sleepless in Seattle' (1993)
Tom Hanks and Meg Ryan starred in the Nora Ephron-directed film, which follows a recently widowed man’s son, who takes it upon himself to find his father a new partner by calling in to a radio talk show. But when the boy’s father, Sam Baldwin, ends up getting on the line to discuss his feelings, a reporter in Baltimore, Annie Reed, catches feelings for him.
Watch Sleepless In Seattle online Stream on Peacock; buy or rent on Apple TV, Prime Video
'To All the Boys I've Loved Before' (2018)
When teen Lara Jean’s love letters get mailed by her little sister, she creates an elaborate plan with one of her past crushes, Peter, to save herself from being too embarrassed. But she must navigate her feelings when the fake relationship with Peter starts to become real. The Susan Johnson-directed film, based on the book series by Jenny Han, stars Lana Condor and Noah Centineo.
Once viewers finish the film, they don’t have to worry because there are also two more movies in the franchise, To All the Boys: P.S. I Still Love You and To All The Boys: Always and Forever.
Watch To All the Boys I Loved Before online Stream on Netflix
'Love and Basketball' (2000)
The Gina Prince-Bythewood-directed film follows two childhood friends, Monica and Quincy, who both share a love for basketball. But as the two begin to fall for each other, their separate journeys in the sport threaten their relationship. The movie stars Sanaa Lathan and Omar Epps.
Watch Love & Basketball online Stream on Max; buy or rent on Prime Video
'Crazy Rich Asians' (2018)
In the movie, Rachel Chu accompanies her longtime boyfriend, Nick, to his best friend’s wedding in Singapore. Once there, she learns Nick’s family is extremely wealthy and he is considered one of the country’s most eligible bachelors. Now she must take on Nick’s disapproving mother and other women vying for his heart. The Jon M. Chu-directed movie, based on a book by Kevin Kwan, stars Constance Wu and Henry Golding.
Watch Crazy Rich Asians online Stream on Hulu; buy or rent on Apple TV, Prime Video
'When Harry Met Sally' (1989)
This rom-com classic, starring Billy Crystal and Meg Ryan, follows two college graduates, Harry Burns and Sally Albright, who meet while sharing a car ride from Chicago to New York. During the trip, they get in an argument about whether men and women can be strictly platonic friends. Fast forward 10 years and they meet again in a bookstore, but they’re confronted with the same question: “Can a man and a woman be friends, without sex getting in the way?” The film was directed by Rob Reiner.
Watch When Harry Met Sally online Buy or rent on Apple TV, Prime Video
'How to Lose a Guy in 10 Days' (2003)
The Donald Petrie-directed movie stars Kate Hudson and Matthew McConaughey. It follows Andie Anderson, an advice columnist, who is trying to push the boundaries with her writing and pitches a story about how to get a man to leave you in 10 days. As for executive Ben Berry, he bets that he can make a woman fall in love with him in 10 days. When Andie and Ben meet, their plans don’t go as they intended them to. The film is based on an illustrated book by Michele Alexander and Jeannie Long.
Watch How to Lose a Guy in 10 Days online Stream on Paramount+; buy or rent online at Apple TV, Prime Video
'My Best Friend's Wedding' (1997)
Julia Roberts, Dermot Mulroney and Cameron Diaz star in the P.J. Hogan-directed rom-com. It follows Julianne Potter and Michael O’Neal, who had a deal to marry each other if they were still single by age 28. But when Michael is set to marry Kimberly, Julianne realizes that she’s actually still in love with him and sets out to stop the wedding.
Watch My Best Friend’s Wedding online buy or rent on Apple TV, Prime Video
'The Proposal' (2009)
Sandra Bullock and Ryan Reynolds star in the Anne Fletcher-directed rom-com. The movie follows Margaret Tate, a pushy boss, who is faced with possible deportation to Canada. She then forces her assistant, Andrew Paxton, to marry her in order to keep her visa status in the U.S. But when she travels to Alaska to meet his eccentric family, they must continue to put on a good front despite things not going as planned.
Watch The Proposal online Stream on Hulu; buy or rent on Apple TV, Prime Video
'Love, Actually' (2003)
The Richard Curtis-directed movie follows the lives of eight different couples who are dealing with their own love lives during the busy December season before Christmas. The star-studded cast includes Hugh Grant, Martine McCutcheon, Liam Neeson, Keira Knightley, Bill Nighy, Laura Linney, Gregor Fisher, Colin Firth, Emma Thompson, Heike Makatsch, Kris Marshall, Martin Freeman, Chiwetel Ejiofor, Andrew Lincoln and Joanna Page.
Watch Love, Actually online Buy or rent on Apple TV, Prime Video
'Roman Holiday' (1953)
The film sees sheltered princess Ann, who takes off for a night while in Rome, but when she falls asleep on a park bench after taking a sedative from her doctor, an American reporter, Joe Bradley, finds her. After bringing Ann back to his apartment for safety, he learns of her real identity. While he plans to try and get an exclusive interview with her, romantic feelings end up getting in the way. The William Wyler-directed movie stars Audrey Hepburn and Gregory Peck.
Watch Roman Holiday online Stream on Paramount+; buy or rent on Apple TV, Prime Video
'Pretty Woman' (1990)
Julia Roberts and Richard Gere star in the Garry Marshall-directed rom-com. The film sees Edward Lewis, a wealthy businessman, hire Vivian Ward, a prostitute, to stay with him for a weekend and attend some social events while he’s on a business trip in Los Angeles. As they learn more about each other, they get closer, but eventually realize there are several challenges as they try to bring together their different worlds.
Watch Pretty Woman online Stream on Hulu; buy or rent on Apple TV, Prime Video
'Crazy, Stupid, Love.' (2011)
The rom-com, directed by Glenn Ficarra and John Requa, sees a middle-aged husband, Cal, whose life changes dramatically when his wife, Emily, asks him for a divorce. In an effort to rediscover his manhood, he enlists help from a newfound friend, Jacob, who has also discovered a new relationship with Hannah. The cast includes Steve Carell, Ryan Gosling, Emma Stone and Julianne Moore.
Watch Crazy, Stupid, Love. online Stream on Hulu; buy or rent on Apple TV, Prime Video
'Pretty in Pink' (1986)
The movie follows Andie, an outcast at her high school, who typically finds herself hanging out with older boss Iona, or her quirky classmate Duckie. Though Duckie has a crush on her, Andie ends up going on a date with one of the rich, popular kids at school, Blane. But as she starts to fall for him, she realizes dating someone in a completely different social sphere is not easy. The Howard Deutch-directed film stars Molly Ringwald, Jon Cryer, Andrew McCarthy and Annie Potts.
Watch Pretty in Pink online Stream on Paramount+; buy or rent on Apple TV, Prime Video
'Upgraded' (2024)
When aspiring art director Ana is upgraded to first class on a work trip, she ends up meeting Will, who mistakes her for her demanding boss, Claire. But when the white lie leads to glamorous events, romance and career opportunities, Ana attempts to keep the truth hidden. The Carlson Young-directed movie stars Camila Mendes and Archie Renaux.
Watch Upgraded online Stream on Prime Video
'How Stella Got Her Groove Back' (1998)
The film — starring Angela Bassett, Taye Diggs and Whoopi Goldberg — sees Stella, a highly successful stockbroker, take a well-deserved vacation to Jamaica with her best friend, Delilah. Along the way, she has an island fling with handsome Winston, but when she realizes she has developed real feelings for him, it complicates her plans to go back home to California. The movie is directed by Kevin Rodney Sullivan.
Watch How Stella Got Her Groove Back online Stream on Hulu; buy or rent on Apple TV, Prime Video
'Moonstruck' (1987)
The Norman Jewison-directed movie follows Loretta, a bookkeeper from Brooklyn, New York, who finds herself in a difficult situation when she catches feelings for the younger brother, Ronny, of the man she is set to marry. The film’s cast includes Cher, Danny Aiello and Nicolas Cage.
Watch Moonstruck online Buy or rent on Apple TV, Prime Video
'Your Place or Mine' (2023)
The film, starring Reese Witherspoon and Ashton Kutcher, sees two long-distance best friends, Debbie Dunn and Peter Coleman, switch lives when Debbie decides to pursue a lifelong dream. Peter volunteers to watch her teen son, but along the way, they each realize that they don’t want their lives to be separate anymore. Aline Brosh McKenna directed the movie.
Watch Your Place or Mine online Stream on Netflix
'Notting Hill' (1999)
The Julia Roberts and Hugh Grant-led movie sees Anna Scott, a famous actress, fall in love with William Thacker, a bookstore owner. But as they grow closer, they struggle to navigate their radically different lifestyles as well as the paparazzi. The film was directed by Roger Michell.
Watch Notting Hill online Stream on Prime Video; buy or rent on Apple TV
'Never Been Kissed' (1999)
Josie Geller, a newspaper reporter, poses as a high school student to research teen culture for a story. As she infiltrates the most popular clique on campus with the help of her brother, Rob, she ends up hitting a speed bump in her investigation when she falls for her English teacher, Sam Coulson. The Raja Gosnell-directed rom-com stars Drew Barrymore, David Arquette and Michael Vartan.
Watch Never Been Kissed online Stream on Starz; buy or rent on Apple TV, Prime Video