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The Most Iconic Movie Proposals Of All Time

In celebration of Valentine’s Day

Call us hopeless romantics, but there’s something incredibly charming about Valentine’s Day. Perhaps it’s because it’s a holiday centered around love — and what’s more charming than that? — or the fact that it falls just after Christmas and Lunar New Year, and gives us another excuse to celebrate and be merry in the middle of winter.

It might be for the heart-shaped decorations everywhere, that chocolate is such a big part of it, or because the day spurs on romantic gestures, such as the most classic one of all — a symbol of commitment in the form of a glistening diamond ring. But, gemstone-encrusted gestures aside, the best way to mark February 14 has to be with a rom-com, especially if it follows a nice meal out, and all the more so if it features an emotional and inspiring proposal scene.

We’ve rounded up some of the most iconic movie proposals of all time (spoiler warning!). Pick one or watch them all in a Valentine Day’s film marathon — just don’t forget to have tissues and lots of chocolate at hand to help you get through them.

Sabrina (1954)
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The plot: Audrey Hepburn stars as Sabrina Fairchild, the daughter of a kind chauffeur who works for the wealthy Larrabee family. Sabrina has grown up enchanted with the Larrabees’ sparkling, privileged world, but she's especially enamored of younger Larrabee brother David (William Holden), a charming womanizer. After she returns from Paris and transformed into a remarkably attractive young woman, she at long last catches David's eye. Determined to manipulate David away from her and into a more financially advantageous marriage, older brother Linus (Humphrey Bogart) pretends to woo Sabrina himself — until he unintentionally falls in love with her.

The scene: After only one dance with the newly debuted Sabrina Fairchild, David Larrabee asks her to marry him. In fact, he calls off his engagement to another woman altogether.

When Harry Met Sally… (1989)
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The plot: Considered by many the best rom-com of all time, When Harry Met Sally… follows the complicated relationship between Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) — who first met as college graduates — as they attempt to navigate adulthood, careers, and their friendship. What they don’t realize is that they’re actually romantically perfect for each other.

The scene: Harry makes an epic, love-affirming proposal to his longtime best friend Sally just as the clock turns to midnight on New Year's Eve. The line that still gets us every time? “When you realize you want to spend the rest of your life with somebody, you want that the rest of your life to start as soon as possible.”

Notting Hill (1999)
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The plot: Julia Roberts and Hugh Grant — rom-com royalty — pair in this evergreen movie. Famous American film star Anna Scott (Roberts) falls in love with very British and very shy travel bookstore owner William Thacker (Grant) during a publicity trip in London to launch her new movie. Problems ensue — as they must, given their different circumstances — but eventually love trumps all.

The scene: After a messy breakup, Will realizes he wants Anna back in his life (because how can you not, when someone tells you “I’m also just a girl standing in front of a boy asking him to love her”). He races to find her and, in front of a room filled with journalists — she’s at a press event — asks her if she would give the relationship another go. “Yes I believe I would,” she tells him. “That’s very good news,” replies Will with classic understatement. “The readers of Horse & Hound will be absolutely delighted.”

A Walk to Remember (2002)
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The plot: A classic for those of us who were teens in the early 2000s, A Walk to Remember tells the story of Landon Carter (Shane West), a troublesome high school senior who falls madly in love with Jamie Sullivan (Mandy Moore), the daughter of a minister, who reveals that she has cancer. As the two embark on a star-crossed romance due to Jamie’s terminal diagnosis, she captures Landon’s heart and ultimately inspires him to turn his life around, while Landon teaches Jamie how to really live.

The scene: The couple spends the evening waiting for a comet to appear through Jamie's new telescope that Landon has built. As they look up at the sky, he pops the question to his dying girlfriend (yes, prepare for a total sob session).

Crazy Rich Asians (2018)
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The plot: The highest-grossing romantic comedy of the 2010s and the movie that made history for Asian American representation on screen is the perfect rom-com to watch on V-Day. A storyline refresher: Rachel Chu (Constance Wu), an NYU economics professor, dates a man named Nick Young (Henry Golding), but doesn’t know he comes from one of Singapore’s most powerful families. As they travel to the island nation to attend Nick’s best friend’s wedding and she discovers exactly how wealthy the family is, drama (of the comedic kind) ensues.

The scene: Besides breaking down barriers, Crazy Rich Asians (based on the book by Kevin Kwan) gave us one of the best proposal scenes ever. After realizing that Nick’s family would never accept her, Rachel decides to go back home. Determined not to let her go, Nick chases after her and ends up proposing on the plane.

Even better, he reveals the ring he’s proposing with once belonged to his mom — a sign she has finally come to accept Rachel.

Whether it be as a sign of commitment to a loved one or an act of self-love, celebrate February 14 by exploring DFS’s range of jewelry, including plenty of creations speckled with glistening gemstones — diamonds are forever, after all.

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