5.4k voters

The Greatest Date Movies Of All Time

Updated March 1, 2021 54.3k votes 5.4k voters 235.0k views126 items

What are the best date night movies? That's a tricky question, because you've got your first date movies and your second date movies...and so on. This list of top films for date night includes a wide variety of different kinds of films that will hopefully make for an excellent evening of snuggling and discussion. Many of these films are some of the best romantic comedies of all time. These are the movies you really can't go wrong watching on date night. Vote up your favorites, vote down any you had to suffer through on bad dates and of course, rerank this list any way you want. You might also be interested in the best movies for couples.

While a list of the best date night movies will likely be dominated by romantic comedies ("rom-coms"), this list also includes some great dramas, some classic funny movies and a handful of horror movies, too. Why? Because not everybody likes Hollywood rom-coms. Sometimes you want to dig a little deeper. Good date night movie ideas can spur some interesting discussion and, in the case of horror movies, can bring you two much closer - literally.

One caveat with the date night movie choices: Please, unless you are absolutely certain your sweetie loves period movies, do not, repeat, do not make them suffer through long, sweepingly epic films like The English Patient. Yes, the movie is romantic but trust us, stick with the lighter fare. The same goes for other great epic movies like the Lord of the Rings trilogy. It's fine if your date is a huge fan, but if not? Bad idea. Also, beware the tearjerker movies. You don't want to be sitting there blubbering like a baby in front of a date when Mufasa dies in The Lion King, do you?

If you're really in doubt, go with one of these highly rewatchable movies and/or a selection from this list of the best movies of all time.

  • 1

    Forrest Gump

    Tom Hanks, Sally Field

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  • 2

    You've Got Mail

    Tom Hanks, Meg Ryan

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    #4 of 12 Movies That Were Eerily Ahead Of Their Time#32 of 83 Great Movies That Take Place In Autumn

  • 3

    Sleepless in Seattle

    Tom Hanks, Meg Ryan

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  • 4

    50 First Dates

    Drew Barrymore, Adam Sandler

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  • 5

    10 Things I Hate About You

    Joseph Gordon-Levitt, Gabrielle Union

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    #47 of 135 The Best Movies Based On Plays#2 of 21 The Most Memorable Prom Dresses In Movies

  • 6

    The Wedding Singer

    Drew Barrymore, Adam Sandler

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  • 7

    The Proposal

    Sandra Bullock, Ryan Reynolds

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  • 8


    Leonardo DiCaprio, Kate Winslet

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  • 9

    How to Lose a Guy in 10 Days

    Kate Hudson, Matthew McConaughey

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  • 10


    John Travolta, Olivia Newton-John

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  • 11


    Demi Moore, Whoopi Goldberg

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  • 12

    Crazy, Stupid, Love.

    Emma Stone, Julianne Moore

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  • 13

    The Princess Bride

    Billy Crystal, Robin Wright

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  • 14

    Lady and the Tramp

    Peggy Lee, Stan Freberg

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    #135 of 357 The Best Musical Movies Of All Time#24 of 534 The Best Animated Films Ever

  • 15

    Sixteen Candles

    John Cusack, Molly Ringwald

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  • 16

    When Harry Met Sally...

    Meg Ryan, Billy Crystal

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  • 17

    The Notebook

    Rachel McAdams, Ryan Gosling

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    #232 of 1,506 The Most Rewatchable Movies#15 of 201 The Best Teen Romance Movies

  • 18

    Love Actually

    Keira Knightley, Elisha Cuthbert

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    #29 of 127 The Best Christmas Movies of All Time#48 of 291 The Greatest Soundtracks of All Time

  • 19

    Sweet Home Alabama

    Reese Witherspoon, Matthew McConaughey

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    #25 of 91 The Funniest Movies About Family#5 of 21 Movies With Places In The Title That Weren't Actually Shot There

  • 20

    A Walk to Remember

    Shane West, Mandy Moore

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  • 21

    Dirty Dancing

    Patrick Swayze, Jennifer Grey

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  • 22

    Pretty Woman

    Julia Roberts, Richard Gere

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  • 23

    Ever After

    Drew Barrymore, Anjelica Huston

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    #13 of 81 The Best Period Romance Movies#58 of 60 The Best Movies to Curl Up And Watch When You're Sick

  • 24

    Mr. & Mrs. Smith

    Angelina Jolie, Brad Pitt

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  • 25

    Never Been Kissed

    Jessica Alba, Drew Barrymore

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    #17 of 72 The Greatest Female-Led Comedy Movies#99 of 252 The Funniest '90s Movies