10 Most Memorable On-Screen Dates

There’s nothing like the movies to show a breathtakingly great date—and a totally terrible one. Check out these 10 cinematic moments for proof.

By Laura Gilbert

Memorable movie date #1: Before Sunrise
After making small talk on a trans-Europe train, Jesse (Ethan Hawke) persuades French-chick Celine (Julie Delpy) to de-board in Vienna for a marathon date that’ll last until his flight home the next morning. They navigate the city’s off-hours streets, bars, churches, and parks, meeting palm-readers, poets, dancers, and cow-portraying actors. Along the way, they discuss art, love, death, and other angsty twenty-something Big Issues.
What we love: The idea that true love may be only as far away as our next plane or train ride.
What could stand for improvement: After that kind of rapport, they really should have exchanged phone numbers or e-mail addresses before parting ways!

Memorable movie date #2: Roman Holiday
Free-spirited Princess Ann (Audrey Hepburn) escapes from her royal quarters and meets gambling-man and journalist Joe (Gregory Peck). He doesn’t tell her he knows her identity, and the two play hooky, dining at a sidewalk café, goofing off at the Mouth of
What captures our imagination about Before Sunrise is the idea that true love may be only as far away as our next plane or train ride.
Truth, and dancing at the Ponte Sant’Angelo before diving into the Tiber to escape her family’s henchmen.
What we love: The whole fairy tale—being a princess, traipsing around Europe, being romanced by a bad boy who’s on his best behavior.
What could stand for improvement: Joe’s initial, self-serving motive when he learns Ann’s identity—to trail her to get a newspaper scoop.

Memorable movie date #3: Serendipity
Reaching for the same pair of gloves in a crowded New York department store just before Christmas, Jonathan (John Cusack) first meets lovable Englishwoman Sara (Kate Beckinsale). The coincidence sets off a heart-warming winter date complete with Rockefeller Center ice skating and conversations about topics ranging from fate to sexual positions.
What we love: Jonathan tending to Sara’s scraped elbow and drawing constellations on her freckles.
What could stand for improvement: That it’s years—and two engagements—before their second date, due to Sara’s belief that fate would bring them together again.

Memorable movie date #4: Pulp Fiction
Hit man Vincent Vega (John Travolta) is supposed to bodyguard his boss’s wife Mia (Uma Thurman). After indulging in a five-dollar shake at a theme restaurant called Jack Rabbit Slim’s, Mia makes Vincent enter a dance contest that they win, and the two victory-tango home.
What we love: Their incredibly frank date-night discussions about everything from foot rubs to uncomfortable silences.
What could stand for improvement: The fact that they were both blindingly high (Mia even OD’s). Isn’t dinner and dancing enough stimulation for one night?

Memorable movie date #5: There’s Something About Mary
Years after a tragic frank, beans, and zipper accident on prom night, dorky Ted (Ben Stiller) still nurses a crush on Mary (Cameron Diaz), so he tracks her down for a second chance. Before the big night, Ted engages in some jitters-busting self-love time, only to answer the door with a glob of…something…on his ear. Assuming it’s hair gel, Mary transfers the goo to her bangs.
What we love: That poor Ted finally gets to make a decent impression.
What could stand for improvement: Mary’s disturbing new ‘do’.

Memorable movie date #6: 50 First Dates
When Hawaiian marine biologist (and notorious womanizer) Henry (Adam Sandler) falls for quirky Lucy (Drew Barrymore), he pulls out all the stops to impress her. He gives her an after-hours tour of the aquarium where he works, introduces her to a sea lion, and plays a song he’d composed for her on his ukulele before heading back to her place. Only one
In Pulp Fiction, you’ve gotta admire the incredibly frank date-night discussion about everything from foot rubs to uncomfortable silences.
problem: Lucy has a rare brain disorder that erases her memory each night, so the next morning she wakes up screaming at finding a “stranger” in her bed.
What we love: Henry’s willingness to win over Lucy’s family in order to get the girl.
What could stand for improvement: The fact that the movie makes light of a totally serious medical condition.

Memorable movie date #7: The Graduate
Benjamin Braddock (Dustin Hoffman) is trysting with family friend Mrs. Robinson, so he’s wary when his parents force him to hang with the Robinson’s daughter Elaine (Katharine Ross). To guarantee the date won’t go well and incite Mrs. Robinson’s wrath, he takes Elaine to a garish burlesque, from which she runs crying. Realizing he’s being a jerk—and that he kinda likes her—he makes it up to her with a kiss and burgers at a drive-in while sharing all (well, most) of his deepest fears.
What we love: When Benjamin starts to drop Elaine off, they turn around and prolong the date instead.
What could stand for improvement: Benjamin brings Elaine to the hotel where he’s been doing the fandango with Elaine’s mom. Bad, bad, idea—especially given all the busboys greet him like a VIP visitor.

Memorable movie date #8: Moonstruck
With her boring-but-safe fiancé off in Italy, widow Loretta (Cher) learns she has a future—and estranged—bad-boy brother-in-law, Ronny (Nicolas Cage). Loretta and Ronny begin an off-limits affair that culminates in a night at Lincoln Center, where the swells of the opera La Bohème seal their relationship.
What we love: That Loretta knows she’s going to hell for sleeping with her fiancé’s brother—but can’t resist his animalistic charms.
What could stand for improvement: That superstitious streak everyone’s harboring that allows them to blame the moon for all these hijinks. Denial, anyone?

Memorable movie date #9: Pretty Woman
For $3,000, Edward (Richard Gere) gets a week of working girl Vivian’s (Julia Roberts) time. After several days of playing arm candy, she gets taken out on the town solo by Edward, who decks her out with a new ball gown, gorgeous jewels, a private jet ride, and tickets to opening night at the San Francisco Opera before settling in for a candlelit game of chess.
What we love: A perfect gentleman with a gold card pulling out all the romantic stops.
What could stand for improvement: Reality check—how likely is a corporate tycoon to do this in everyday life?

Memorable movie date #10: The Way We Were
When former classmates nerdy Katie (Barbra Streisand) and hunky Hubbell (Robert Redford) coincidentally reunite years later, Katie invites the WWII navy officer back to her place for coffee. There, Hubbell gets naked and sloppily makes some moves before passing out on top of poor Babs. Undeterred, she cooks breakfast and irons his suit the next day, only to find out that her sweetie has absolutely no memory of last night’s encounter.
What we love: Katie’s eternal optimism about dating a guy who’d usually be considered out of her league, looks- and popularity-wise.
What could stand for improvement: Katie’s self-esteem. She spends most of the movie falling all over herself, thrusting her number at Hubbell—but then again, He’s Just Not That Into You wouldn’t be written for decades to come.

Freelance writer Laura Gilbert’s favorite love story is Fight Club.

Did we leave out a memorable movie date scene that you think deserves recognition? Let us know and we may feature it in an upcoming article.

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