11 Movies like ‘When Harry Met Sally’ for Fans of Heartwarming Witty Rom-Coms

“When Harry Met Sally” premiered in 1989, yet many movie watchers still enjoy the film’s storyline. Since its debut, similar movies about romance, friendship, and a touch of comedy have hit the big screens.

Harry Burns and Sally Albright, two college graduates who shared a car ride from Chicago to New York City, had opposing thoughts about whether a man and woman can remain friends without falling in love.

They believed they would never cross paths again, but destiny had them running into each other at different times. They eventually became close friends, with a connection that deepened as time passed.

British native Charles often attends weddings with his closest friends, where fun, love, and mishaps occur. However, despite attending many weddings, he is far from becoming a groom. In one wedding where Charles stands as the best man, he meets an American woman, Carrie.

It was undoubtedly love at first sight for Charles, but circumstances and miscommunication seem to keep them apart even with undeniable chemistry and a fantastic night together. It takes more than three more weddings and a funeral to make them realize their heart’s desire.

The holiday season is truly a time when magic and miracles happen; Jonathan and Sara are a testament to that. When the two meet in New York City by chance and share a wonderful evening, they decide to leave their future to destiny.

Sara writes her phone number inside a book while Jonathan pens his on a $5 bill. Sara believes that destiny would bring them together should the stars align. So they let the book and bill circulate through the city, hoping it would return to them.

After years of living their own lives, Sara and Jonathan continue to think about each other, hoping to find the only items that will bring them back together. “Serendipity” premiered in 2001, starring John Cusack and Kate Beckinsale as the lead characters.

After experiencing a horrible 13th birthday party, Jenna Rink wishes to be “30, flirty, and thriving.” She later wakes up 30 years old and has to navigate through adulthood, realizing it wasn’t like what she imagined.

While working on her career in fashion, she reconnects with her childhood friend, Matt, and realizes their friendship is more important than the popularity she chased as a teen. As she slowly develops feelings for Matt, Jenna must make decisions that will dictate the course of her life.

“13 Going on 30” premiered in 2004 and starred Jennifer Garner as Jenna and Mark Ruffalo as Matt. Other cast members include Judy Greer, Andy Serkis, Kathy Baker, and Phil Reeves.

Set in the early days of the internet, Joe Fox and Meg Ryan find themselves as online penpals who get along well. They confide in each other about their lives without knowing their true identities.

However, Joe and Meg know each other in real life — they are rivals in their businesses. They soon find themselves falling for each other, thanks to the power of digital technology. “You’ve Got Mail” premiered in 1998 and stars Tom Hanks and Meg Ryan as the main characters.

Grumpy weatherman Phil Connors repeatedly wakes up reliving the same day, Groundhog Day. While initially hating his situation, Phil learned to use it to have fun and do things he had never done before.

However, while stuck in the time loop, he falls for his colleague, Rita, whom he wants to win over. As days repeat, he tries to get things right with her. “Groundhog Day” premiered in 1993 and stars Bill Murray, Andie MacDowell, Chris Elliott, and Stephen Tobolowsky.

After several unplanned encounters, American actress Anna Scott fell for William Thacker, a British bookseller, in a store in Notting Hill, West London. However, navigating through romance is challenging, given Anna’s celebrity status.

Since debuting in 1999, “Notting Hill” has become among the most well-loved romantic comedies with memorable quotes. The film stars Hugh Grant and Julia Roberts as romantic love interests.

Sasha Tran and Marcus Kim were childhood friends who took their relationship further but later grew apart as adults. Now living completely different lives, Sasha is a celebrity chef and restauranteur, while Marcus is a musician in their hometown.

When fate brings them together, Sasha and Marcus slowly realize that they enjoy each other’s company more than anything. However, they soon become separated again by distance. “Always Be My Maybe” premiered in 2019 and stars Ali Wong, Randall Park, and James Saito.

Melanie Carmichael is living her best life as a fashion designer in New York City and fiancée to a wealthy man. However, before walking down the aisle to marry her most cherished man, she must return home to Pigeon Creek, Alabama, and secretly file for divorce.

Everyone in her new life has no clue of Melanie’s past, including her marriage to her high school sweetheart, Jake Perry. The problem is Jake won’t sign the papers. As Melanie embarks on a mission to convince him while reliving her days in Alabama, she realizes there is no place like home with Jake.

Marcus Graham built his career in an advertising agency, but when he’s not focused at work, he gets in bed with women and leaves them there. However, his life takes an unexpected turn when he falls for his boss, who, behind the corporate life, is just like him.

Mary Fiore is a talented wedding planner who is excellent at her job. She one day meets a man, Steve, who saves her from a potential accident. Slowly, they get to know each other and start to develop attraction.

Fiore’s life takes an unexpected turn when she learns Steve is the groom of one of her upcoming weddings. She must now navigate her professional life while handling her feelings for Steve.

Rosie and Alex have been best friends since they were children, and as they grew older, they promised to stay by each other’s side. However, Rosie couldn’t fulfill the promise when she became pregnant with another man and hid it from her best friend.

As they navigate life separately, Rosie and Alex remain connected. Despite their feelings for each other and undeniable attraction, circumstances and timing always keep them apart.

“Love Rosie” premiered in 2014 and starred Lily Collins, Sam Claflin, Christian Cooke, Jaime Winstone, Suki Waterhouse, Lorcan Cranitch, Ciaran McGlynn, Tamsin Egerton, and Jamie Beamish.

Other great romantic comedies include “Long Shot” (2019), “The Lovebirds” (2020), “Just Go With It” (2011), “Crazy, Stupid, Love” (2011), “Monster-In-Law” (2005), and “Made of Honor” (2008).