350 voters

The Greatest Movie Wedding Proposals

Updated June 3, 2019 1.7k votes 350 voters 10.4k views20 items

What do you envision as the perfect marriage proposal? Flowers? A shiny diamond engagement ring? Nervous would-be groom on bended knee? Leave it to Hollywood to provide audiences with some of the most memorable moments of romance. These are the greatest movie wedding proposals on film.

Some of the guys who proposed on this list were never great with words. Rocky asked Adrian to marry him in Rocky II, with the not so smooth line, “I was wondering if you wouldn't mind marrying me very much?" Even still, the Italian Stallion's proposal was sweet and sincere, and how could a girl say "no" to Rocky? Johnny Cash was a bit more mischievous with his proposal. He invited his love, June Carter, on stage to sing a duet with him. Then, the music legend would not stop playing the song until she agreed to marry him.

Not every one of these proposals even ended with a “yes” (Sorry, Ben from Knocked Up). But his promise to fill the empty jewelry box he proposed with was so sweet that it had to be listed here. And since it is the 21st century, it should be important to note, that not every proposal on this list featured the man asking the woman.

From a custom-built walk-in shoe closet to Tiffany’s in New York City to standing outside in pouring rain, these are the movie marriage proposals that stole our hearts and made us go “awww, that’s sweet.”

Did we miss any of your favorite wedding proposals in movies? Let us know in the comments section. Also, be sure to upvote for the best silver screen marriage proposals that made the list.
  • Just because Melanie (Reese Witherspoon) and Andrew (Patrick Dempsey) don't wind up together at the end of Sweet Home Alabama, it doesn't make his marriage proposal any less sweet. Andrew has Melanie close her eyes, when she opens them, she's in Tiffany's and Andrew tells her to pick out a wedding ring.
    • Actors: Reese Witherspoon, Matthew McConaughey, Dakota Fanning, Patrick Dempsey, Candice Bergen
    • Released: 2002
    • Directed by: Andy Tennant
    • Screenplay by: C. Jay Cox
    Dreamy proposal?
  • Lucy (Sandra Bullock) is a lonely transit token collector in Chicago. Just when you think that Jack (Bill Pullman) and Lucy are not going to wind up together, Jack drops a diamond engagement ring into Lucy's token tray. He proposes in front of his very opinionated family, and the pair seals the deal with a kiss right there in Lucy's booth.
    • Actors: Sandra Bullock, Monica Keena, Bill Pullman, Ally Walker, Peter Boyle
    • Released: 1995
    • Directed by: Jon Turteltaub
    • Screenplay by: Daniel G. Sullivan, Frederic Lebow
    Dreamy proposal?

    More While You Were Sleeping 

    #61 of 134 The Best Christmas Movies of All Time#153 of 252 The Funniest '90s Movies#178 of 366 'Old' Movies Every Young Person Needs To Watch In Their Lifetime

  • My Big Fat Greek Wedding is an uproarisous comedy filled with a larger than life Greek family and plenty of interesting uses for Windex. Toula (Nia Vardalos) meets Ian (John Corbett), a non-Greek quiet type, and the mismatched pair fall in love. His proposal is sweet and simple, "I don't know how to say this... will you marry me?"
    • Actors: Nia Vardalos, Andrea Martin, Joey Fatone, John Corbett, Lainie Kazan
    • Released: 2002
    • Directed by: Joel Zwick
    • Screenplay by: Nia Vardalos
    Dreamy proposal?
  • Margaret (Sandra Bullock) forces her assistant Andrew (Ryan Reynolds) to marry her to avoid deportation back to her native Canada. Andrew agrees to the deal only if he gets a promotion. The sham works for a while, and the mismatched couple actually do fall in love. When the jig is up and Margaret is about to get deported, Andrew 
    proposes for real in front of all their co-workers, saying, “marry me because I’d like to date you."
    • Actors: Sandra Bullock, Ryan Reynolds, Betty White, Malin Åkerman, Mary Steenburgen
    • Released: 2009
    • Directed by: Anne Fletcher
    • Screenplay by: Pete Chiarelli
    Dreamy proposal?

    More The Proposal 

    #6 of 115 The Greatest Date Movies of All Time#9 of 836 The Greatest Chick Flicks Ever Made#391 of 1,137 The Absolute Funniest Movies Of All Time