20 of the Sweetest, Funniest, and Most Outrageous Meet-Cutes in Rom-Com History

·13 min read
Matthew McConaughey And Jennifer Lopez In 'The Wedding Planner'
Matthew McConaughey And Jennifer Lopez In 'The Wedding Planner'

Matthew McConaughey and Jennifer Lopez in a scene from the film 'The Wedding Planner.' Credit - Columbia Pictures/Getty Images

A movie star wanders into a bookstore and falls hopelessly in love with its owner. A wedding planner is literally swept off her feet by a handsome doctor who saves her from being crushed by a runaway dumpster. A mother walks into her home and mistakes her daughter’s boyfriend for an intruder, only to fall for him. When it comes to the ingredients of a romantic comedy, there’s nothing quite as charming as the meet-cute, that first encounter between romantic heroes that walks the alluring line between relatability and fantasy.

It’s no surprise, then, that the device itself has inspired a new romantic comedy. In Meet Cute, released this week on Peacock, Sheila (Kaley Cuoco) and Gary (Pete Davidson) experience the same meet-cute and subsequent first date over and over again, thanks to a magical tanning-bed time machine. The movie is both an expansion and an inversion of the meet-cute concept, one that glories in the sweet excitement of meeting someone new but also recognizes that a moment shared by two strangers can only carry so much meaning for the future.

In movies through the ages, meet-cutes have ranged from zany to thrilling, from romantic to silly. The mark of a good one is not only a clever or entertaining setup, but also how the story follows through. With that in mind, we’ve rounded up 20 of the sweetest, funniest, and most outrageous romantic comedy meet-cutes in movie history.

It Happened One Night (1934)

When spoiled runaway heiress Ellie (Claudette Colbert) boards a Greyhound bus to escape her father’s wrath after eloping with a fortune-seeking pilot, she’s looking for anonymity. But when she’s forced to share a seat with fellow passenger Peter (Clark Gable)—an unemployed journalist who recognizes Ellie and is well aware of her scandalous backstory—sparks fly. The unlikely duo strike a deal that will give Peter the exclusive on Ellie’s marriage and ensure that she reunites with her husband. But after a series of heart-warming misadventures on their journey, Ellie and Peter discover that their arrangement might be developing into something more.

The Lady Eve (1941)

Con artist Jean (Barbara Stanwyck), along with her father and his partner, is out to trap the fabulously wealthy yet nerdy beer heir Charles (Henry Fonda) as they travel on an ocean liner. While all the women aboard the ship throw themselves at Charles, Jean makes her move at dinner by tripping him and then admonishing him for breaking the heel off her shoe, catching the bachelor off-guard. While Charles quickly falls for Jean, she also unexpectedly develops feelings for him, eventually calling off the con—but not before Charles dumps her. Things really take a turn when Jean returns, looking for both revenge and a way to win back Charles by posing as a fake aristocrat, the Lady Eve Sidwich.

Roman Holiday (1953)

American journalist Joe (Gregory Peck) stumbles on the story and the romance of a lifetime after he rescues a lost woman he finds sleeping on a bench in Rome, taking her back to his apartment for safety. The next morning, Joe discovers that the young woman is actually Princess Ann (Audrey Hepburn), a royal from an unidentified European country who ran away from her guardians to explore the city. While Joe sees the opportunity for an exclusive story that will make his career, an unexpected romance between him and Ann changes everything.

Charade (1963)

Expat American interpreter Regina (Audrey Hepburn) is on vacation in the French Alps and on the brink of divorce from her husband when she meets Peter (Cary Grant), a fellow American who engages her in some decidedly forward repartee at the ski lodge when he brings her friend’s kid back to his mother. Upon returning home, Regina finds out that her husband secretly absconded with a fortune and was murdered. So she and Peter, who seems to have an endless supply of pseudonyms, embark on a madcap journey to retrieve the money, all while dodging those who would kill her for it.

Claudine (1974)

Single mother Claudine (Diahann Carroll) is caught in a catch-22. She’s working as a maid for a wealthy white family in the suburbs—a job she has to keep secret due to the broken welfare system—and she can still barely make ends meet for herself and her six children in Harlem. One day, while taking out the trash at work, she meets Rupert (James Earl Jones), an ebullient garbage collector who pursues her despite her reservations about dating because of her kids. While Rupert and Claudine face challenges both personal and systemic, they ultimately decide to take a chance on their love.

Read more: The 15 Best Romantic Comedies from the Early 2000s

Moonstruck (1987)

Widow Loretta (Cher) doesn’t love her boyfriend Johnny, but she’s agreed to marry him because he’s a “sweet man.” While Johnny is in Sicily visiting his dying mother, Loretta pays a visit to his estranged and volatile brother Ronny (Nicolas Cage) at his bakery, meeting him for the first time to ask him to attend the wedding. Ronny, who blames Johnny for an accident that caused him to lose his hand, flies into a fury at Loretta; they continue the conversation at Ronny’s apartment, where Loretta cooks him a meal and they argue again before sharing a kiss and sleeping together, causing Loretta to reevaluate what she really wants for her future.

Coming to America (1988)

After Crown Prince Akeem (Eddie Murphy) breaks off his arranged marriage, he reasons that the best place to find a new wife and his future queen is in Queens, New York. After arriving, Akeem attends a rally for Black Awareness Week, where he spots Lisa (Shari Headley), the daughter of a local fast food restaurant owner and an organizer of the rally. After she asks attendees to donate to help save a park, Akeem determines that her kind heart makes her an excellent candidate to be his wife; he hides his wealth and status and applies to work at her father’s restaurant, a McDonald’s knock-off called McDowell’s, where he finally introduces himself to Lisa while offering to take out her garbage.

Pretty Woman (1990)

Broke sex worker Vivian (Julia Roberts) is looking to make rent when she propositions Edward (Richard Gere), a ruthless corporate raider, in the red-light district of Hollywood Boulevard. Edward, who’s visiting from out of town, is lost, unsure of how to return to his hotel, and unable to drive the car with a manual transmission that he’s been lent. So he hires Vivian to give him directions, with her eventually taking over driving as well. Charmed by her wit and ambition, Edward hires Vivian to appear as his girlfriend at his business events for the week. But things take a turn after the two begin to have feelings for one another.

Love Jones (1997)

Poet Darius (Larenz Tate) and photographer Nina (Nia Long) meet while waiting for a drink at a bohemian jazz nightclub in Chicago. Later that night, Darius, onstage for a poetry reading, changes the title of his love poem to include Nina’s name. Following another run-in at a record store, in which Nina, fresh off a breakup, rebuffs his advances, Darius convinces her to go out with him, leading to a heady romance that’s jeopardized once Nina’s ex re-enters the picture.

How Stella Got Her Groove Back (1998)

Middle-aged stockbroker and single mother Stella (Angela Bassett) takes a much-needed vacation to Jamaica at the behest of her best friend. While Stella’s just looking to unwind from the daily grind, she catches the eye of Winston (Taye Diggs), a local. After approaching Stella, the two share a meal where, along with the usual introductions, they discover their nearly two-decade age difference, which unsettles Stella. Nonetheless, the two share a steamy affair while she’s on the island. What Stella doesn’t anticipate is how her feelings for Winston will linger when she returns to normal life.

Read more: The Rom-Com Is Making a Comeback for All the Right Reasons

You’ve Got Mail (1998)

Independent children’s bookstore owner Kathleen (Meg Ryan) can’t stand book megastore heir Joe (Tom Hanks), the man who’s actively trying to put her and her shop out of business—so much so that when she meets him at a publishing party, she openly fights with him. But unbeknownst to each of them, they’ve already met online. They’ve been baring their souls to one another for months in an AOL chat which they started after meeting in a chat room for “over 30s.” After Joe as “NY152” proposes that they meet in person and discovers that Kathleen is the “Shop Girl” he’s fallen in love with, he continues to conceal his identity and attempts to woo her as himself.

But I’m a Cheerleader (1999)

Naive high school cheerleader Megan (Natasha Lyonne) is basically happy—except she doesn’t like kissing her boyfriend Jared and prefers looking at her fellow cheerleaders. That, combined with her affinity for Melissa Etheridge and an interest in vegetarianism, is enough for her conservative Christian family to conclude that Megan is showing “lesbian tendencies.” So they send her to conversion therapy camp. It’s there that she meets Graham (Clea DuVall), her roommate who is also an unapologetically queer rebel. In their initial meeting in their room, Graham, sprawled across her bed, uses her introduction as a way to both shock and flirt with Megan, setting the scene for something more.

Notting Hill (1999)

American movie star Anna (Julia Roberts) wanders into a struggling travel bookstore in London owned by Will (Hugh Grant), who is starstruck yet respectful. Later that day, the pair meets again when they literally run into each other on the street, with Will spilling his cup of orange juice on Anna’s shirt, then offering to let her freshen up at his apartment. Before she leaves, Anna spontaneously kisses Will, despite having a boyfriend, leading the two to pursue a romance.

The Wedding Planner (2001)

Career-focused wedding planner Mary (Jennifer Lopez) has just landed the biggest gig of her life when she steps onto the streets of San Francisco and gets her Gucci heel stuck in a manhole cover. As she struggles to free her foot, a wayward cab driver hits a dumpster, causing it to careen down the hill right toward Mary—until Steve (Matthew McConaughey), a pediatrician, heroically pulls her out of the way. While Mary and Steve have undeniable chemistry after he saves her life (and her shoe), they soon discover that he’s the groom for her high-stakes event, leaving both to grapple with their burgeoning feelings for one another.

Serendipity (2001)

Strangers Jonathan (John Cusack) and Sara (Kate Beckinsale) meet when they both reach for the same pair of black cashmere gloves during a busy day of Christmas shopping; after bickering over the conflict, with Sara ultimately winning the gloves, the two share dessert at New York City’s famous Serendipity 3 shop and discuss the role of fate before choosing to go their separate ways. But just as they say goodbye, Sara tosses Jonathan one of the gloves—leaving a piece of their connection intact for years to come.

Read more: 20 Rom-Coms That Put a New Spin on an Old Genre

Maid in Manhattan (2002)

Hotel maid and single mother Marisa (Jennifer Lopez) does something very out of character one day and tries on the designer coat of a wealthy hotel guest while cleaning her room. Dressed in the other woman’s clothes, Marisa is mortified when her young son Ty introduces her to the hotel guest he’s just befriended because of his dog, senatorial candidate Chris (Ralph Fiennes). Chris invites Marisa and Ty to go for a walk, where it’s clear that they are attracted to one another, but Marisa must decide if the romance is worth continuing the ruse.

My Big Fat Greek Wedding (2002)

Toula (Nia Vardalos) is stuck in a rut. Then, while working at her family’s Greek restaurant, she sees and instantly falls in love with Ian (John Corbett), a WASP-y teacher who she can’t stop staring at. Their brief encounter inspires Toula to take charge of her life by going back to school, changing her style, and going to work at her aunt’s travel agency. While happily working at her new job, Toula once again runs into Ian, and this time she’s ready to start something.

Something’s Gotta Give (2003)

Notorious aging bachelor Harry (Jack Nicholson) is known for his womanizing ways and affinity for women under 30, but he’s out of his element when he meets Erica (Diane Keaton), an accomplished playwright of his own age—who happens to be the mother of his girlfriend. The pair butts heads after Erica mistakes Harry for an intruder at her Hamptons home when he and her daughter drop by for the weekend unannounced. But they’re forced to cohabitate after Harry has a heart attack, leading both to reconsider their initial assumptions about one another.

Hitch (2005)

Alex (Will Smith), better known to his clients as “Hitch,” is a dating coach who specializes in helping men woo women with the goal of developing long-term relationships. His smooth moves and thoughtful observations have an almost perfect success rate for his clients, but Hitch faces his biggest challenge yet when he meets Sara (Eva Mendes), a gossip columnist. While out one night at a bar, Hitch spots Sara across the room and asks the bartender for her drink order with the intention of bringing her another one, but he’s intercepted by a boorish and pushy man who refuses to respect Sara’s request to be left alone. After Hitch pretends to be her boyfriend to shake the man, he eventually charms her into agreeing to a date—not yet aware that his dating coach business is about to be the subject of her next story.

Set It Up (2018)

Harried assistants Harper (Zoey Deutch) and Charlie (Glen Powell) are overworked and exhausted, thanks to their respective workaholic bosses, Kirsten (Lucy Liu) and Rick (Taye Diggs). After running into each other late one night in the elevator bank of the building where they both work, each on a separate mission to procure dinner for their boss, they happily solve each others’ crises: Harper has no cash to pay for the food she ordered, while Charlie has money but forgot to place an order. The next day, when Harper meets up with Charlie to pay him back, they hatch a scheme to stage a meet-cute for their bosses in the work elevator in the hopes that a romantic relationship between the two will mean more work-life balance for them. Their plan is successful—but it’s not just Kristen and Rick who end up catching feelings.

Fire Island (2022)

In this contemporary retelling of Pride and Prejudice, a group of queer friends reunite one summer for a week of community and partying on New York’s Fire Island. Best friends Howie (Bowen Yang) and Noah (Joel Kim Booster) spot some potential romantic candidates at a bar on their first day on the island, but leave before making introductions. After Howie trips and falls, Charlie (James Scully), a cute doctor they clocked earlier, helps him to his feet and invites him to watch the sunset. Charlie and Howie’s flirtation leads to Noah meeting Will (Conrad Ricamora), Charlie’s stoic and standoffish best friend, with whom Noah shares a mutual attraction and disdain.