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The Greatest Date Movies of All Time

Updated January 15, 2021 56.9k votes 5.3k voters 229.3k views125 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. And, if your favorite date night film is missing, add it!

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. A good date night movie 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 me, 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.

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  • Forrest Gump1
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    Forrest Gump

    Tom Hanks, Sally Field

    Released1994

    Directed byRobert Zemeckis

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  • You've Got Mail2
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    You've Got Mail

    Tom Hanks, Meg Ryan

    Released1998

    Directed byNora Ephron

    You've Got Mail is a 1998 American romantic comedy-drama film directed by Nora Ephron,... more on WikipediaAmazon buy button
  • The Proposal3
    695
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    The Proposal

    Sandra Bullock, Ryan Reynolds

    Released2009

    Directed byAnne Fletcher

    The Proposal is a 2009 American romantic comedy film set in Sitka, Alaska. Directed by Anne... more on WikipediaAmazon buy button

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  • 50 First Dates4
    830
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    50 First Dates

    Drew Barrymore, Adam Sandler

    Released2004

    Directed byPeter Segal

    50 First Dates is a 2004 American romantic comedy film directed by Peter Segal. Henry Roth... more on WikipediaAmazon buy button

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  • Sleepless in Seattle5
    772
    476

    Sleepless in Seattle

    Tom Hanks, Meg Ryan

    Released1993

    Directed byNora Ephron

    Sleepless in Seattle is a 1993 American romantic comedy-drama film directed and co-written by... more on WikipediaAmazon buy button
  • Titanic6
    690
    400

    Titanic

    Leonardo DiCaprio, Kate Winslet

    Released1997

    Directed byJames Cameron

    Titanic is a 1997 American epic romance and disaster film directed by James Cameron. A... more on WikipediaAmazon buy button

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  • 10 Things I Hate About You7
    869
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    10 Things I Hate About You

    Joseph Gordon-Levitt, Gabrielle Union

    Released1999

    Directed byGil Junger

    10 Things I Hate About You is a 1999 American romantic comedy film directed by Gil Junger, and... more on WikipediaAmazon buy button
  • The Wedding Singer8
    495
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    The Wedding Singer

    Drew Barrymore, Adam Sandler

    Released1998

    Directed byFrank Coraci

    The Wedding Singer is a 1998 romantic comedy film written by Tim Herlihy and directed by Frank... more on WikipediaAmazon buy button
  • How to Lose a Guy in 10 Days9
    564
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    How to Lose a Guy in 10 Days

    Kate Hudson, Matthew McConaughey

    Released2003

    Directed byDonald Petrie

    How to Lose a Guy in 10 Days is a 2003 American romantic comedy film directed by Donald... more on WikipediaAmazon buy button
  • Crazy, Stupid, Love.10
    528
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    Crazy, Stupid, Love.

    Emma Stone, Julianne Moore

    Released2011

    Directed byJohn Requa, Glenn Ficarra

    Crazy, Stupid, Love is a 2011 American romantic comedy-drama film directed by Glenn Ficarra... more on WikipediaAmazon buy button

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  • Grease11
    711
    414

    Grease

    John Travolta, Olivia Newton-John

    Released1978

    Directed byRandal Kleiser

    Grease is a 1978 American musical romantic comedy-drama film directed by Randal Kleiser and... more on WikipediaAmazon buy button

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  • Ghost12
    599
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    Ghost

    Demi Moore, Whoopi Goldberg

    Released1990

    Directed byJerry Zucker

    Ghost is a 1990 American romantic fantasy/crime thriller film starring Patrick Swayze, Demi... more on WikipediaAmazon buy button
  • The Princess Bride13
    966
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    The Princess Bride

    Billy Crystal, Robin Wright

    Released1987

    Directed byRob Reiner

    The Princess Bride is a 1987 American romantic comedy fantasy adventure film directed and... more on WikipediaAmazon buy button

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  • Sixteen Candles14
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    Sixteen Candles

    John Cusack, Molly Ringwald

    Released1984

    Directed byJohn Hughes

    Sixteen Candles is a 1984 American coming-of-age comedy film starring Molly Ringwald, Michael... more on WikipediaAmazon buy button

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  • When Harry Met Sally...15
    693
    508

    When Harry Met Sally...

    Meg Ryan, Billy Crystal

    Released1989

    Directed byRob Reiner

    When Harry Met Sally… is a 1989 American romantic comedy film written by Nora Ephron and... more on WikipediaAmazon buy button
  • Lady and the Tramp16
    436
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    Lady and the Tramp

    Peggy Lee, Stan Freberg

    Released1955

    Directed byWilfred Jackson, Hamilton Luske, Clyde Geronimi

    Lady and the Tramp is a 1955 American animated musical romance film directed by Clyde... more on WikipediaAmazon buy button

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  • The Notebook17
    998
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    The Notebook

    Rachel McAdams, Ryan Gosling

    Released2004

    Directed byNick Cassavetes

    The Notebook is a 2004 American romantic drama film directed by Nick Cassavetes and based on... more on WikipediaAmazon buy button

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  • Love Actually18
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    Love Actually

    Keira Knightley, Elisha Cuthbert

    Released2003

    Directed byRichard Curtis

    Love Actually is a 2003 British Christmas-themed romantic comedy film written and directed by... more on WikipediaAmazon buy button
  • A Walk to Remember19
    479
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    A Walk to Remember

    Shane West, Mandy Moore

    Released2002

    Directed byAdam Shankman

    A Walk to Remember is a 2002 American coming-of-age romantic tragedy film directed by Adam... more on WikipediaAmazon buy button
  • Ever After20
    281
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    Ever After

    Drew Barrymore, Anjelica Huston

    Released1998

    Directed byAndy Tennant

    Ever After is a 1998 American romantic comedy-drama film inspired by the fairy tale... more on WikipediaAmazon buy button
  • Mr. & Mrs. Smith21
    448
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    Mr. & Mrs. Smith

    Angelina Jolie, Brad Pitt

    Released2005

    Directed byDoug Liman

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  • Sweet Home Alabama22
    458
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    Sweet Home Alabama

    Reese Witherspoon, Matthew McConaughey

    Released2002

    Directed byAndy Tennant

    Sweet Home Alabama is a 2002 American romantic comedy film directed by Andy Tennant. A young... more on WikipediaAmazon buy button
  • Pretty Woman23
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    Pretty Woman

    Julia Roberts, Richard Gere

    Released1990

    Directed byGarry Marshall

    Pretty Woman is a 1990 American romantic comedy film directed by Garry Marshall. A... more on WikipediaAmazon buy button
  • Dirty Dancing24
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    Dirty Dancing

    Patrick Swayze, Jennifer Grey

    Released1987

    Directed byEmile Ardolino

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  • Never Been Kissed25
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    Never Been Kissed

    Jessica Alba, Drew Barrymore

    Released1999

    Directed byRaja Gosnell

    Never Been Kissed is a 1999 romantic comedy film produced by 20th Century Fox and Drew... more on WikipediaAmazon buy button