If you adore the classic romantic comedy When Harry Met Sally, you’re probably always on the lookout for more charming, witty, and heartwarming movies that give you those same warm fuzzy feelings. Well, look no further! We’ve compiled a list of 18 fantastic films that capture a similar spirit and are sure to make you laugh, cry, and fall in love all over again. So grab some popcorn, snuggle up on the couch, and get ready to swoon with these must-watch movies for any When Harry Met Sally fan.
1. Sleepless in Seattle (1993)
Sleepless in Seattle reunites rom-com dream team Tom Hanks and Meg Ryan in a story that’s sure to tug at your heartstrings. Sam Baldwin (Hanks) is a recently widowed father living in Seattle with his young son Jonah. When Jonah calls into a radio talk show to find his dad a new wife, Sam reluctantly gets on the line and pours his heart out about how much he misses his late wife. Women across the country are touched, including journalist Annie Reed (Ryan) in Baltimore. Despite being engaged, Annie becomes taken with Sam’s story and writes him a letter suggesting they meet atop the Empire State Building on Valentine’s Day.
Sleepless in Seattle has all the ingredients of a perfect romantic comedy – an unlikely love story, charming leads with undeniable chemistry, and a healthy dose of humor and heart. Hanks is incredibly endearing as the grieving Sam trying to move on, while Ryan lights up the screen as the hopeless romantic Annie. With nods to the classic romance An Affair to Remember, this film is a love letter to destiny and the idea that there’s someone out there for everyone. It will make you laugh, cry, and believe in the magic of love again.
Most Memorable Quote: “Well, I’m gonna get out of bed every morning… breathe in and out all day long. Then, after a while I won’t have to remind myself to get out of bed every morning and breathe in and out.”
2. You’ve Got Mail (1998)
You’ve Got Mail brings Hanks and Ryan together again, this time as rival bookstore owners Joe Fox and Kathleen Kelly. Unbeknownst to them, they’re also falling for each other online, having met in an “over-30s” chat room. Joe is the heir to the Fox Books superstore empire, while Kathleen runs the quaint family bookshop The Shop Around the Corner. As Fox Books opens a new location right around the corner from Kathleen’s store, the two become professional nemeses, all the while continuing their anonymous online romance.
Directed by Nora Ephron, who also helmed Sleepless in Seattle, You’ve Got Mail is a sweet and clever update of the classic film The Shop Around the Corner. Hanks and Ryan’s chemistry is as charming as ever, making you root for them even when they’re at odds. The film also serves as a nostalgic time capsule of the early days of the Internet and the excitement of an email notification proclaiming “you’ve got mail!” With witty dialogue, likable supporting characters, and a lovely fall in New York backdrop, this movie is like a cozy cup of tea – warm, comforting, and good for the soul.
Most Memorable Quote: “The odd thing about this form of communication is that you’re more likely to talk about nothing than something. But I just want to say that all this nothing has meant more to me than so many somethings.”
3. 50 First Dates (2004)
For a slightly different take on the rom-com formula, check out 50 First Dates. Adam Sandler stars as Henry, a veterinarian living in Hawaii known for his fear of commitment and penchant for short-lived flings with tourists. That is until he meets Lucy (Drew Barrymore), a charming local who captures his heart. The catch? Due to a car accident, Lucy suffers from short-term memory loss and can’t remember anything from the previous day. So every morning, Henry must find new ways to reintroduce himself and make Lucy fall in love with him all over again.
While the premise may sound a bit silly, 50 First Dates is surprisingly sweet and heartfelt. Sandler and Barrymore, who previously starred together in The Wedding Singer, have an easy, natural rapport that makes you believe in and root for their unconventional love story. The Hawaiian setting is gorgeous, and the supporting cast, including Rob Schneider and Sean Astin, provide plenty of laughs. But at its core, this film is a touching story about the power of love and the lengths we’ll go to for the ones we care about.
Most Memorable Quote: “So every day, I get to fall in love with you all over again.”
4. Notting Hill (1999)
Notting Hill is a charming British rom-com that asks the question: What if a regular bloke fell in love with a movie star? That’s exactly what happens to William Thacker (Hugh Grant), a mild-mannered London bookshop owner whose life is turned upside down when famous American actress Anna Scott (Julia Roberts) walks into his store. The two embark on a whirlwind romance, but their different lifestyles and Anna’s celebrity status threaten to tear them apart.
Written by Richard Curtis, who also penned Four Weddings and a Funeral and Love Actually, Notting Hill is a witty and heartwarming fairy tale romance. Grant is at his most charmingly befuddled, while Roberts positively glows as the beautiful but vulnerable Anna. The colorful cast of supporting characters, including William’s quirky flatmate Spike and his kooky family and friends, add humor and heart. With its London setting and themes of fame and love against the odds, Notting Hill is a delightful, feel-good watch.
Most Memorable Quote: “I’m just a girl, standing in front of a boy, asking him to love her.”
5. Bridget Jones’s Diary (2001)
Based on the beloved novel by Helen Fielding, Bridget Jones’s Diary follows the trials and tribulations of its titular heroine, a 30-something single woman in London determined to improve her life and find love. Bridget (Renée Zellweger) finds herself torn between two men – her dashing but caddish boss Daniel Cleaver (Hugh Grant) and the seemingly uptight but kind-hearted lawyer Mark Darcy (Colin Firth). As she navigates her career, friendships, and romantic entanglements, Bridget learns to accept and love herself, flaws and all.
Bridget Jones’s Diary is a hilarious and relatable comedy with a lot of heart. Zellweger is pitch-perfect as the endearingly awkward Bridget, while Grant and Firth are equally appealing as her potential love interests. The film’s diary format allows us to get inside Bridget’s head, from her innermost insecurities to her wry observations on life and love. With its humor, romance, and message of self-acceptance, this movie is the ultimate feel-good watch for anyone who’s ever felt like a bit of a mess.
Most Memorable Quote: “It is a truth universally acknowledged that when one part of your life starts going okay, another falls spectacularly to pieces.”
6. Serendipity (2001)
Do you believe in destiny? That’s the question at the heart of Serendipity, a sweet and whimsical romantic comedy. During the busy Christmas shopping season in New York City, Jonathan (John Cusack) and Sara (Kate Beckinsale) meet cute while reaching for the same pair of gloves at Bloomingdale’s. There’s an instant spark, but Sara believes their meeting is too perfect to be mere coincidence. She puts their future in the hands of fate, writing her name and number inside a book and selling it to a used bookstore, while Jonathan writes his on a $5 bill. Years later, on the eve of her wedding, Sara wonders if she made the right choice as she and Jonathan search for each other and the clues they left behind.
Serendipity is a charming modern fairy tale that will make you want to believe in happy endings. Cusack and Beckinsale have a lovely, easy chemistry, and the film’s magical realism adds a touch of enchantment to the bustling New York backdrop. With supporting turns from Jeremy Piven and Molly Shannon as the leads’ best friends, this film is a light and breezy watch that will leave you with a smile on your face.
Most Memorable Quote: “You don’t have to understand. You just have to have faith.”
7. The Holiday (2006)
If you’re looking for a cozy and heartwarming watch, The Holiday is the perfect choice. This delightful romantic comedy follows two women, Iris (Kate Winslet) and Amanda (Cameron Diaz), who swap homes for the holidays to escape their relationship troubles. Iris, a London journalist, heads to Amanda’s luxurious LA mansion, while Amanda, a high-powered movie trailer editor, settles into Iris’s cozy English cottage. During their getaways, both women unexpectedly find new romances – Iris with Amanda’s charming brother Graham (Jude Law), and Amanda with Iris’s endearing friend Miles (Jack Black).
The Holiday is the ultimate feel-good movie, with its picturesque settings, lovable characters, and themes of finding love and happiness in unexpected places. Winslet and Diaz are both wonderful as the heartbroken but resilient leads, while Law and Black provide plenty of charm and humor as their new love interests. With a fantastic supporting cast that includes Eli Wallach and Edward Burns, this film is a warm hug in movie form – perfect for a chilly winter’s night or anytime you need a pick-me-up.
Most Memorable Quote: “I understand feeling as small and as insignificant as humanly possible. And how it can actually ache in places you didn’t know you had inside you.”
8. 27 Dresses (2008)
27 Dresses is a fun and frothy romantic comedy that’s sure to delight fans of the genre. Jane (Katherine Heigl) is the ultimate bridesmaid – she’s been in 27 weddings and has the dresses to prove it. But while she’s always the bridesmaid, never the bride, Jane dreams of her own happy ending with her boss George (Edward Burns), whom she’s secretly in love with. When Jane’s younger sister Tess (Malin Akerman) comes to town and catches George’s eye, Jane finds herself planning their wedding while questioning her own love life. Enter Kevin (James Marsden), a cynical wedding reporter who senses a story in Jane’s bridesmaid history. As Kevin shadows Jane for his article, the two spar and banter, slowly developing feelings for each other.
27 Dresses is a charming and predictable rom-com elevated by the likability of its leads. Heigl is endearing as the selfless and romantic Jane, while Marsden brings a playful edge to the role of the jaded journalist. The film pokes fun at wedding culture while still celebrating the joy and love of the occasion. With its mix of humor, heart, and romance, 27 Dresses is a delightful watch for anyone who loves a good love story.
Most Memorable Quote: “I feel like I found out my favorite love song was written about a sandwich.”
9. (500) Days of Summer (2009)
For a more unconventional take on the romantic comedy, look no further than (500) Days of Summer. This clever and bittersweet film follows the 500-day relationship between Tom (Joseph Gordon-Levitt), a hopeless romantic greeting card writer, and Summer (Zooey Deschanel), the beautiful but commitment-phobic woman he falls for. Told in a non-linear format, the movie jumps back and forth through the highs and lows of their time together, from their meet-cute at work to their devastating breakup and its aftermath.
(500) Days of Summer is a refreshingly honest and realistic look at modern love and heartbreak. Gordon-Levitt and Deschanel have an effortless chemistry, making you root for them even as you realize they may not be meant to be. With its inventive storytelling, quirky humor, and killer soundtrack, this film is a must-watch for anyone who’s ever fallen in love or had their heart broken. It’s a reminder that love isn’t always a fairy tale, but that there’s beauty and growth to be found even in the pain of a relationship ending.
Most Memorable Quote: “Just because she likes the same bizarro crap you do doesn’t mean she’s your soul mate.”
10. Crazy, Stupid, Love (2011)
Crazy, Stupid, Love is a hilarious and heartwarming ensemble comedy that explores love and relationships at different stages of life. Cal (Steve Carell) is blindsided when his high school sweetheart and wife of 25 years, Emily (Julianne Moore), asks for a divorce. Adrift and out of the dating game, Cal meets smooth-talking player Jacob (Ryan Gosling), who takes him under his wing and teaches him how to pick up women. Meanwhile, Cal’s 13-year-old son Robbie is in love with his 17-year-old babysitter Jessica, who has a crush on Cal, while Jacob unexpectedly falls for Hannah (Emma Stone), a law student who resists his usual charms.
With its all-star cast and interweaving storylines, Crazy, Stupid, Love is a delight from start to finish. Carell brings his signature awkward humor to the role of the newly single Cal, while Gosling is effortlessly charming as the suave Jacob. Moore, Stone, and Marisa Tomei (as a woman Cal picks up at a bar) round out the fantastic ensemble. The film deftly balances laugh-out-loud moments with genuine emotion, exploring the joys and challenges of love at different ages. It’s a smart, funny, and touching movie that will make you believe in the power of love, even when it’s crazy and stupid.
Most Memorable Quote: “I’m wildly unhappy, and I’m trying to buy it, and it’s not working.”
11. About Time (2013)
About Time is a charming and heartfelt romantic comedy with a time-travel twist. When Tim (Domhnall Gleeson) turns 21, his father (Bill Nighy) reveals a secret: The men in their family can travel back in time to moments they’ve already experienced. Tim decides to use this power to improve his love life, starting with getting a girlfriend. He meets Mary (Rachel McAdams), a charming American, and falls for her instantly. Using his time-travel abilities, Tim tries to create the perfect relationship with Mary, learning along the way that even with the power to change the past, life and love can’t always be perfect.
Written and directed by Richard Curtis (Love Actually, Notting Hill), About Time is a sweet and moving film that’s as much about family and the passage of time as it is about romance. Gleeson is endearing as the awkward but well-meaning Tim, while McAdams brings her usual warmth and likability to the role of Mary. But it’s Nighy who steals the show as Tim’s wise and loving father, their relationship forming the emotional core of the movie. With its mix of humor, heart, and a touch of magic, About Time is a feel-good movie that will make you appreciate the little moments in life and the people you love.
Most Memorable Quote: “We’re all traveling through time together, every day of our lives. All we can do is do our best to relish this remarkable ride.”
12. Something’s Gotta Give (2003)
Something’s Gotta Give is a delightful romantic comedy that proves it’s never too late to find love. Diane Keaton stars as Erica Barry, a successful playwright who finds herself unexpectedly falling for her daughter’s much older boyfriend, Harry Sanborn (Jack Nicholson). When Harry has a heart attack at Erica’s beach house, he ends up staying with her to recuperate, leading to a series of hilarious and heartwarming moments as they navigate their growing attraction.
With sharp wit, relatable characters, and a refreshing focus on romance later in life, Something’s Gotta Give is a must-watch for fans of When Harry Met Sally. Keaton and Nicholson’s chemistry is undeniable, and the film’s exploration of love, vulnerability, and second chances will leave you feeling warm and fuzzy inside.
Most Memorable Quote: “The last time I was in the hospital, I was having my son, Charlie, and while they were stitching me up, I was writing jokes for Johnny Carson.”
13. Crazy, Stupid, Love (2011)
Crazy, Stupid, Love is a charming and hilarious ensemble comedy that follows multiple storylines of love and relationships. At the center of the film is Cal (Steve Carell), a middle-aged man who finds himself newly single after his wife Emily (Julianne Moore) asks for a divorce. Determined to get back in the dating game, Cal enlists the help of smooth-talking player Jacob (Ryan Gosling) to teach him how to pick up women. Meanwhile, Cal’s son Robbie is in love with his babysitter Jessica, who has a crush on Cal, and Jacob unexpectedly falls for Hannah (Emma Stone), a law student who resists his usual charms.
With its all-star cast, clever writing, and mix of humor and heart, Crazy, Stupid, Love is a delightful addition to the rom-com genre. The film’s exploration of love at different ages and stages of life will resonate with fans of When Harry Met Sally, while its surprising twists and turns keep you engaged from start to finish.
Most Memorable Quote: “I’m wildly unhappy, and I’m trying to buy it, and it’s not working.”
14. The Proposal (2009)
The Proposal is a fun and charming romantic comedy that puts a fresh spin on the “fake relationship” trope. Sandra Bullock stars as Margaret Tate, a high-powered book editor who faces deportation to Canada when her visa expires. To stay in the country, she convinces her long-suffering assistant Andrew Paxton (Ryan Reynolds) to marry her in exchange for a promotion. To keep up the ruse, Margaret accompanies Andrew to his family’s home in Alaska for his grandmother’s 90th birthday, where they must pretend to be a loving couple.
With its beautiful Alaskan setting, witty banter, and undeniable chemistry between Bullock and Reynolds, The Proposal is a delightful watch for fans of When Harry Met Sally. The film’s exploration of a fake relationship turning into something real is both funny and heartwarming, while the supporting cast, including Betty White as Andrew’s feisty grandmother, adds to the movie’s charm.
Most Memorable Quote: “Margaret, will you marry me? Because I’d like to date you.”
15. The Holiday (2006)
If you’re looking for a cozy and heartwarming romantic comedy to watch during the holiday season, look no further than The Holiday. This delightful film follows two women, Amanda (Cameron Diaz) and Iris (Kate Winslet), who decide to swap homes for the holidays to escape their relationship troubles. Amanda, a high-powered movie trailer editor from Los Angeles, trades places with Iris, a British journalist living in a charming English cottage. During their getaways, both women unexpectedly find new romances – Amanda with Iris’s charming brother Graham (Jude Law), and Iris with Miles (Jack Black), a friendly film composer.
With its picturesque settings, lovable characters, and themes of finding love and happiness in unexpected places, The Holiday is a perfect feel-good movie for fans of When Harry Met Sally. The film’s exploration of starting over and taking chances will resonate with viewers, while the chemistry between the leads will make you root for their happiness.
Most Memorable Quote: “I understand feeling as small and as insignificant as humanly possible. And how it can actually ache in places you didn’t know you had inside you.”
16. 13 Going on 30 (2004)
13 Going on 30 is a charming and nostalgic romantic comedy that combines elements of fantasy and coming-of-age stories. Jennifer Garner stars as Jenna Rink, a 13-year-old girl in 1987 who dreams of being popular and grown-up. During her 13th birthday party, Jenna makes a wish to be 30 years old and wakes up to find herself magically transformed into her 30-year-old self (Garner) in 2004. As she navigates her new adult life as a successful magazine editor, Jenna realizes that she may have lost touch with what truly matters, including her childhood best friend Matt (Mark Ruffalo).
With its sweet message about staying true to yourself and the importance of friendship, 13 Going on 30 is a delightful watch for fans of When Harry Met Sally. Garner’s charming performance as the adult Jenna with a teenage mindset will make you laugh and reminisce about your own childhood dreams, while her chemistry with Ruffalo adds a touch of romance to the story.
Most Memorable Quote: “I don’t want to be original, I want to be cool!”
17. The Wedding Singer (1998)
Set in the colorful and nostalgic world of the 1980s, The Wedding Singer is a sweet and hilarious romantic comedy that showcases the undeniable chemistry between Adam Sandler and Drew Barrymore. Sandler stars as Robbie Hart, a kind-hearted wedding singer who falls in love with Julia Sullivan (Barrymore), a waitress engaged to a womanizing jerk. As Robbie helps Julia plan her wedding, the two grow closer, but their timing always seems to be off.
With its catchy soundtrack, vibrant 80s fashion, and plenty of laughs, The Wedding Singer is a must-watch for fans of When Harry Met Sally. Sandler and Barrymore’s sweet and funny performances will make you root for their characters’ happiness, while the film’s exploration of finding love when you least expect it will leave you with a warm, fuzzy feeling inside.
Most Memorable Quote: “Once again, things that could have been brought to my attention YESTERDAY!”
18. Love Actually (2003)
Love Actually is a charming and heartwarming ensemble romantic comedy that follows multiple storylines exploring love in its many forms. Set primarily in London during the holiday season, the film features an all-star cast, including Hugh Grant, Emma Thompson, Alan Rickman, Keira Knightley, and Colin Firth, among others. Each character’s story is unique, ranging from a newly elected Prime Minister falling for a staff member to a writer escaping to France after his wife’s infidelity and falling in love with his Portuguese housekeeper.
With its mix of humor, heart, and a touch of holiday magic, Love Actually is a perfect feel-good movie for fans of When Harry Met Sally. The film’s exploration of love in all its complexity – from the joy of falling in love to the pain of heartbreak – will resonate with viewers, while its charming performances and interconnected storylines keep you engaged from start to finish.
Most Memorable Quote: “If you look for it, I’ve got a sneaky feeling you’ll find that love actually is all around.”
These 18 movies capture the charm, wit, and heart of When Harry Met Sally, each offering their own unique take on love, friendship, and the complexities of relationships. Whether you’re in the mood for a classic romance, a nostalgic comedy, or a feel-good ensemble film, these movies are sure to leave you with a smile on your face and a warm feeling in your heart. So grab some popcorn, snuggle up on the couch, and get ready to fall in love with these delightful romantic comedies.
