Movies Gallery The 24 best meet-cutes in rom-com history Some of our favorite onscreen couples met in the most adorable, unexpected ways. By Cristina Everett and Mary Sollosi Mary Sollosi Mary Sollosi is the former assistant features editor at Entertainment Weekly. She left EW in 2022. EW's editorial guidelines Updated on February 9, 2024 01:23PM EST Close Zooey Deschanel and Joseph Gordon-Levitt in '(500) Days of Summer'; Meg Ryan and Billy Crystal in 'When Harry Met Sally; Claire Danes and Leonardo DiCaprio in 'Romeo + Juliet'. Photo: Courtesy Everett Collection (3) Ah, the movie meet-cute. Two people meet by chance, leading to a blossoming romance. For as standard as the meet-cute has become in romantic comedies, we can't help but swoon every time watching these moments — and the more specific the meeting, the better. Even if they ultimately set up unrealistic goals for our own love lives, there's something so universal about casually bumping into the person who might just be "the one," especially when you're least expecting it. We've assembled our picks for the 24 sweetest meet-cutes in rom-com history, including awkward first encounters and life-changing moments of serendipity. 01 of 24 The Holiday (2006) Eli Wallach and Kate Winslet in 'The Holiday'. Zade Rosenthal/Columbia Pictures The two couples at the center of The Holiday may meet pretty cute, but when Iris (Kate Winslet) gives a ride home to her neighbor Arthur (Eli Wallach) while on vacation in Los Angeles, the new friends' introduction takes the meta gold medal. "Well, this was some meet-cute," he observes. She doesn't know the term, so he provides an example: "It's how two characters meet in a movie. Say a man and a woman both need something to sleep in, and they both go to the same men's pajama department. And the man says to the salesman, 'I just need bottoms.' The woman says, 'I just need a top.' They look at each other, and that's the meet-cute." We want to see that one happen! 02 of 24 The Big Sick (2017) Zoe Kazan and Kumail Nanjiani in 'The Big Sick'. Nicole Rivelli/Lionsgate Kumail (Kumail Nanjiani) first meets Emily (Zoe Kazan) after a stand-up show of his, when he confronts her for heckling him during his set. She argues that she was cheering him on, and he explains that any yelling at all during a comedy show counts as heckling. "So if I yelled out, like, 'You're amazing in bed,' that would be a heckle?" she asks. "Yeah," he replies. "It would be an accurate heckle." 03 of 24 Hitch (2005) Eva Mendes in 'Hitch'. Columbia Pictures Just as date doctor Hitch (Will Smith) tries to approach Sara (Eva Mendes) in a bar, another guy cuts him off — but so much the better. Hitch swoops in and pretends to be Sara's boyfriend to get rid of the poor slob whose tired lines are failing on her. Once that guy's gone, though, even the smooth-talking Hitch finds he's met his match. 04 of 24 Serendipity (2001) Miramax/Courtesy Everett Collection While doing some holiday shopping at a crowded Bloomingdale's in Manhattan, both Jonathan Trager (John Cusack) and Sara Thomas (Kate Beckinsale) reach for the same pair of black cashmere gloves. 05 of 24 Notting Hill (1999) Hugh Grant and Julia Roberts in 'Notting Hill'. Universal Pictures After being smitten by her in his bookshop, Will Thacker (Hugh Grant) spills his orange juice on movie star Anna Scott (Julia Roberts) when he literally runs into her on the sidewalk corner outside of his apartment. In the most chivalrous way possible, he invites her to change at his place. 06 of 24 Annie Hall (1977) Diane Keaton and Woody Allen in 'Annie Hall'. Courtesy Everett Collection Though they technically first meet on the court during a game of doubles tennis, it's inside the clubhouse where Annie Hall (Diane Keaton) stumbles over her words in the most nervous, most charming way and gets the attention of Alvy Singer (Woody Allen). 07 of 24 Trainwreck (2015) Bill Hader and Amy Schumer in 'Trainwreck'. Universal Pictures On assignment to profile a sports doctor, Amy (Amy Schumer) sits down with Aaron (Bill Hader) and we quickly learn why she is the least likely, yet best fit for him. 08 of 24 50 First Dates (2004) Drew Barrymore and Adam Sandler in '50 First Dates'. Sony Pictures Henry Roth (Adam Sandler) gets the attention of Lucy Whitmore (Drew Barrymore) after learning she is fond of building little log cabins using her breakfast waffles at a local diner. But, after helping her make a waffle door with the use of a toothpick as a hinge, he learns she has no short-term memory and must continue to win her over each day. 09 of 24 Reality Bites (1994) Winona Ryder in 'Reality Bites'. Universal Pictures College valedictorian Lelaina Pierce (Winona Ryder) and MTV-like executive Michael Grates (Ben Stiller) met by accident — literally. After rolling her eyes at his yuppie-like demeanor while parked side by side at a stoplight, Lelaina flicks her cigarette into Michael's convertible, thus causing him to crash into her car. 10 of 24 Fools Rush In (1997) Salma Hayek in 'Fools Rush In'. Columbia Pictures/Courtesy Everett Collection After some coaxing, Alex Whitman (Matthew Perry) lets Isabel Fuentes (Salma Hayek) cut in front of him while in line for the bathroom at a Mexican restaurant. If you ask her, it was a sign of good things to come. 11 of 24 The Wedding Planner (2001) Matthew McConaughey and Jennifer Lopez in 'The Wedding Planner'. Ron Batzdorff In what may be the most clichéd damsel-in-distress scene in any rom-com, wedding planner Mary Fiore (Jennifer Lopez) gets her Gucci heel stuck in a manhole cover at the same exact moment a rogue dumpster is barreling down a hilly San Francisco street, heading right toward her. Her modern-day knight in shining armor, Steve Edison (Matthew McConaughey), comes to her rescue by, well, shoving her out of the way. Ah, love. 12 of 24 Before Sunrise (1995) Ethan Hawke and Julie Delpy in 'Before Sunrise'. Columbia Pictures All it took was an arguing German couple on a train ride to Vienna to break the ice between Jesse (Ethan Hawke) and Celine (Julie Delpy). After some small talk, the two end up spending the night talking and walking the streets of the Austrian capital, only to agree to meet at the exact same spot six months later. 13 of 24 (500) Days of Summer (2009) Joseph Gordon-Levitt and Zooey Deschanel in '(500) Days of Summer'. Fox Searchlight / Everett Collection As soon as Tom (Joseph Gordon-Levitt) laid eyes on Summer (Zooey Deschanel) at their downtown office building, he knew he had to meet her. And as soon as Summer began singing along to the music he was listening to on his headphones in the elevator they shared, he knew he had to be with her. 14 of 24 Love Actually (2003) Hugh Grant and Martine McCutcheon in 'Love Actually'. Universal Pictures Upon meeting the new British Prime Minister (Hugh Grant), Natalie (Martine McCutcheon) — a new junior member of the household staff — nervously drops a number of expletives during their first introduction. 15 of 24 Sleepless in Seattle (1993) Meg Ryan and Tom Hanks in 'Sleepless in Seattle'. TriStar Pictures/Everett Collection Though viewers know early on that widower Sam Baldwin (Tom Hanks) and unhappily engaged Annie Reed (Meg Ryan) are made for each other, we don't see the two finally meet until the last scene in this Nora Ephron classic. In a nod to An Affair to Remember, the two agree to meet atop the Empire State Building on Valentine's Day and what transpires is the sweetest long-awaited introduction between two strangers. 16 of 24 Something's Gotta Give (2003) Diane Keaton and Jack Nicholson in 'Something's Gotta Give'. Bob Marshak/Columbia Pictures This may be the most awkward meet-cute in rom-com history but the charm of Jack Nicholson's Henry and Diane Keaton's Erica make it less so. When Erica escapes to her Hamptons house in search of some R&R, the last thing she would expect would be a run-in with her daughter (Amanda Peet) and her daughter's new, much (much) older boyfriend, Henry. So when Henry winds up having a heart attack while having sex with Erica's daughter, guess who has to stay behind to take care of him? 17 of 24 Bridesmaids (2011) Kristen Wiig in 'Bridesmaids'. Universal Pictures Most people wouldn't be as patient as police officer Rhodes (Chris O'Dowd) was when he pulls over a tipsy Annie (Kristen Wiig) for erratic driving. It's no surprise he becomes easily taken by her goofy antics and hilarious dance moves. 18 of 24 Out of Sight (1998) Jennifer Lopez and George Clooney in 'Out of Sight'. Universal Pictures When genetically blessed bank robber Jack Foley (George Clooney) and federal agent Karen Sisco (Jennifer Lopez) are first introduced in the trunk of a car as they are being whisked away from prison, it's only a matter of seconds before sparks fly. In a meta-meet-cute moment, among the random topics the two discuss while in tight quarters is 1975's Three Days of the Condor, in which fugitive CIA analyst Joe Turner (Robert Redford) finds himself in a similar predicament with the sultry Kathy Hale (Faye Dunaway) after taking her hostage while on the run. 19 of 24 My Big Fat Greek Wedding (2002) Nia Vardalos in 'My Big Fat Greek Wedding'. IFC Films/Courtesy Everett Collection Toula Portokalos (Nia Vardalos) first meets Ian Miller (John Corbett) when she serves his table at her family's Greek restaurant. She is immediately taken with him, struggling to form sentences as she pours coffee for Ian and his buddy. Their meet-cute continues a few months later when Ian catches sight of Toula working at a travel agency and can't stop passing by the window. 20 of 24 Maid in Manhattan (2002) Ralph Fiennes and Jennifer Lopez in 'Maid in Manhattan'. Columbia Pictures/Courtesy Everett Collection Hotel maid Marisa Ventura (Jennifer Lopez) is trying on a guest's discarded designer clothes when her adorable son Ty (Tyler Posey) brings by a dashing politician named Christopher (Ralph Fiennes). Ty introduces the two to get his mother's permission to walk Christopher's dog, and Chris sees Marisa as a glamorous society woman. 21 of 24 Roman Holiday (1953) Gregory Peck and Audrey Hepburn in 'Roman Holiday'. Courtesy Everett Collection While in Rome, Princess Ann (Audrey Hepburn) is tired of her royal duties and decides to sneak out one night. American journalist Joe Bradley (Gregory Peck) is slated to report on her upcoming press conference but does not recognize her when he stumbles upon her sleeping on a park bench. He takes her to his apartment to sleep it off, and gradually comes to realize who she is, leading him to take her on a charming trip around Rome as they get to know each other without labels. —Kevin Jacobsen 22 of 24 Romeo + Juliet (1996) Claire Danes and Leonardo DiCaprio in 'Romeo + Juliet'. 20th Century-Fox/Getty Images This classic tale of star-crossed lovers is updated to a modern setting, with Romeo (Leonardo DiCaprio) and Juliet (Claire Danes) coming from rival family businesses. They meet at a party, spotting each other from opposite sides of a fish tank. Love at first sight. —K.J. 23 of 24 How Stella Got Her Groove Back (1998) Angela Bassett and Taye Diggs in 'How Stella Got Her Groove Back'. 20th Century Fox Stella Payne (Angela Bassett) is a single mother more invested in her successful career as a stockbroker than her love life. After some persuading, she takes a trip to Jamaica where she meets young chef's assistant Winston Shakespeare (Taye Diggs) at breakfast. —K.J. 24 of 24 When Harry Met Sally (1989) Meg Ryan and Billy Crystal in 'When Harry Met Sally...'. Courtesy Everett Collection College graduates Harry (Billy Crystal) and Sally (Meg Ryan) have a mutual connection that brings them together before carpooling to New York from Chicago. They charmingly banter over whether men and women can just be friends without sex complicating things before parting ways. In the ensuing years, they bump into each other in a series of meet-cute-esque situations, finding themselves on the same flight one year and a bookstore another year. —K.J.