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The Greatest Date Movies of All Time 

Ranker Film
Originally by
Updated February 14, 2020 64.8k votes 4.8k voters 219.3k views 172 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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1
The Princess Bride is listed (or ranked) 1 on the list The Greatest Date Movies of All Time
wiabux added Billy Crystal, Robin Wright, André the Giant

Released: 1987

Directed by: Rob Reiner

The Princess Bride is a 1987 American romantic comedy fantasy adventure film directed and co-produced by Rob Reiner. It was adapted by William Goldman from his 1973 novel of the same name. The ...more

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2
Forrest Gump is listed (or ranked) 2 on the list The Greatest Date Movies of All Time
Tom Hanks, Sally Field, Robin Wright

Released: 1994

Directed by: Robert Zemeckis

Forrest Gump is a 1994 American epic romantic-comedy-drama film based on the 1986 novel of the same name by Winston Groom. The film was directed by Robert Zemeckis and stars Tom Hanks, Robin ...more

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3
The Notebook is listed (or ranked) 3 on the list The Greatest Date Movies of All Time
Rachel McAdams, Ryan Gosling, James Garner

Released: 2004

Directed by: Nick Cassavetes

The Notebook is a 2004 American romantic drama film directed by Nick Cassavetes and based on the novel of the same name by Nicholas Sparks. The film stars Ryan Gosling and Rachel McAdams as a ...more

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4
Pretty Woman is listed (or ranked) 4 on the list The Greatest Date Movies of All Time
Julia Roberts, Richard Gere, Hank Azaria

Released: 1990

Directed by: Garry Marshall

Pretty Woman is a 1990 American romantic comedy film directed by Garry Marshall. A down-on-her-luck Hollywood working girl (Julia Roberts) is hired by a wealthy businessman (Richard Gere) to be ...more

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5
Love Actually is listed (or ranked) 5 on the list The Greatest Date Movies of All Time
Keira Knightley, Elisha Cuthbert, Liam Neeson

Released: 2003

Directed by: Richard Curtis

Love Actually is a 2003 British Christmas-themed romantic comedy film written and directed by Richard Curtis. The screenplay delves into different aspects of love as shown through ten separate ...more

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6
50 First Dates is listed (or ranked) 6 on the list The Greatest Date Movies of All Time
Drew Barrymore, Adam Sandler, Dan Aykroyd

Released: 2004

Directed by: Peter Segal

50 First Dates is a 2004 American romantic comedy film directed by Peter Segal and written by George Wing. The film stars Adam Sandler as a lothario veterinarian and Drew Barrymore as an ...more

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7
You've Got Mail is listed (or ranked) 7 on the list The Greatest Date Movies of All Time
Tom Hanks, Meg Ryan, Sara Ramirez

Released: 1998

Directed by: Nora Ephron

You've Got Mail is a 1998 American romantic comedy-drama film directed by Nora Ephron, starring Tom Hanks and Meg Ryan. It was written by Nora and Delia Ephron based on the 1937 play Parfumerie ...more

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8
Titanic is listed (or ranked) 8 on the list The Greatest Date Movies of All Time
vinothan1000 added Leonardo DiCaprio, Kate Winslet, Kathy Bates

Released: 1997

Directed by: James Cameron

Titanic is a 1997 American epic romance and disaster film directed by James Cameron. A seventeen-year-old aristocrat (Kate Winslet) falls in love with a kind but poor artist (Leonardo DiCaprio) ...more

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9
When Harry Met Sally... ... is listed (or ranked) 9 on the list The Greatest Date Movies of All Time
Meg Ryan, Billy Crystal, Carrie Fisher

Released: 1989

Directed by: Rob Reiner

When Harry Met Sally… is a 1989 American romantic comedy film written by Nora Ephron and directed by Rob Reiner. It stars Billy Crystal as Harry and Meg Ryan as Sally. The story follows the ...more

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10
10 Things I Hate About Y... is listed (or ranked) 10 on the list The Greatest Date Movies of All Time
wiabux added Joseph Gordon-Levitt, Gabrielle Union, Heath Ledger

Released: 1999

Directed by: Gil Junger

10 Things I Hate About You is a 1999 American romantic comedy film directed by Gil Junger, and a modern retelling of William Shakespeare's The Taming of the Shrew. After finding out his crush ...more

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11
Sleepless in Seattle is listed (or ranked) 11 on the list The Greatest Date Movies of All Time
Tom Hanks, Meg Ryan, Rosie O'Donnell

Released: 1993

Directed by: Nora Ephron

Sleepless in Seattle is a 1993 American romantic comedy-drama film directed and co-written by Nora Ephron. Based on a story by Jeff Arch, it stars Tom Hanks as Sam Baldwin and Meg Ryan as Annie

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12
The Wedding Singer is listed (or ranked) 12 on the list The Greatest Date Movies of All Time
Drew Barrymore, Adam Sandler, Steve Buscemi

Released: 1998

Directed by: Frank Coraci

The Wedding Singer is a 1998 romantic comedy film written by Tim Herlihy and directed by Frank Coraci. It stars Adam Sandler as a wedding singer in the 1980s and Drew Barrymore as a waitress ...more

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13
The Proposal is listed (or ranked) 13 on the list The Greatest Date Movies of All Time
KennethDempsey added Sandra Bullock, Ryan Reynolds, Betty White

Released: 2009

Directed by: Anne Fletcher

The Proposal is a 2009 American romantic comedy film set in Sitka, Alaska. Directed by Anne Fletcher and written by Peter Chiarelli, the film features Sandra Bullock and Ryan Reynolds in the ...more

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14
Ghost is listed (or ranked) 14 on the list The Greatest Date Movies of All Time
Demi Moore, Whoopi Goldberg, Patrick Swayze

Released: 1990

Directed by: Jerry Zucker

Ghost is a 1990 American romantic fantasy/crime thriller film starring Patrick Swayze, Demi Moore, Tony Goldwyn, and Whoopi Goldberg. It was written by Bruce Joel Rubin and directed by Jerry ...more

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15
Grease is listed (or ranked) 15 on the list The Greatest Date Movies of All Time
John Travolta, Olivia Newton-John, Stockard Channing

Released: 1978

Directed by: Randal Kleiser

Grease is a 1978 American musical romantic comedy-drama film directed by Randal Kleiser and produced by Paramount Pictures. It is based on Warren Casey and Jim Jacobs' 1971 musical of the same ...more

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16
Crazy, Stupid, Love. is listed (or ranked) 16 on the list The Greatest Date Movies of All Time
Emma Stone, Julianne Moore, Ryan Gosling

Released: 2011

Directed by: John Requa, Glenn Ficarra

Crazy, Stupid, Love is a 2011 American romantic comedy-drama film directed by Glenn Ficarra and John Requa, and written by Dan Fogelman. It stars Steve Carell, Ryan Gosling, Julianne Moore, Emma ...more

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17
Dirty Dancing is listed (or ranked) 17 on the list The Greatest Date Movies of All Time
Patrick Swayze, Jennifer Grey, Jerry Orbach

Released: 1987

Directed by: Emile Ardolino

Dirty Dancing is a 1987 American romantic drama film. Written by Eleanor Bergstein and directed by Emile Ardolino, the film stars Patrick Swayze and Jennifer Grey in the lead roles, as well as ...more

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18
How to Lose a Guy in 10 ... is listed (or ranked) 18 on the list The Greatest Date Movies of All Time
wiabux added Kate Hudson, Matthew McConaughey, Bebe Neuwirth

Released: 2003

Directed by: Donald Petrie

How to Lose a Guy in 10 Days is a 2003 romantic comedy film, directed by Donald Petrie, starring Kate Hudson and Matthew McConaughey. It is based on a short cartoon book of the same name by ...more

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19
Sixteen Candles is listed (or ranked) 19 on the list The Greatest Date Movies of All Time
wiabux added John Cusack, Molly Ringwald, Joan Cusack

Released: 1984

Directed by: John Hughes

Sixteen Candles is a 1984 American coming-of-age comedy film starring Molly Ringwald, Michael Schoeffling and Anthony Michael Hall. It was written and directed by John Hughes.

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20
Mr. & Mrs. Smith is listed (or ranked) 20 on the list The Greatest Date Movies of All Time
wiabux added Angelina Jolie, Brad Pitt, Jennifer Morrison

Released: 2005

Directed by: Doug Liman

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21
My Best Friend's Wedding... is listed (or ranked) 21 on the list The Greatest Date Movies of All Time
wiabux added Julia Roberts, Dermot Mulroney, Rupert Everett

Released: 1997

Directed by: P. J. Hogan

My Best Friend's Wedding is a 1997 American romantic comedy film directed by P.J. Hogan. When a woman's long-time friend (Dermot Mulroney) reveals he's engaged, she (Julia Roberts) realizes she ...more

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22
Serendipity is listed (or ranked) 22 on the list The Greatest Date Movies of All Time
Kate Beckinsale, John Cusack, Bridget Moynahan

Released: 2001

Directed by: Peter Chelsom

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23
A Walk to Remember is listed (or ranked) 23 on the list The Greatest Date Movies of All Time
Shane West, Mandy Moore, Peter Coyote

Released: 2002

Directed by: Adam Shankman

A Walk to Remember is a 2002 American coming-of-age romantic tragedy film directed by Adam Shankman, based on the 1999 novel by Nicholas Sparks. Popular rebel Landon Carter (Shane West) is ...more

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24
Overboard is listed (or ranked) 24 on the list The Greatest Date Movies of All Time
looksharp added Goldie Hawn, Kurt Russell, Roddy McDowall

Released: 1987

Directed by: Garry Marshall

Overboard is a 1987 American romantic comedy film starring Goldie Hawn and Kurt Russell. It was directed by Garry Marshall, produced by Roddy McDowall, and loosely inspired by the 1974 Italian ...more

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25
Pretty in Pink is listed (or ranked) 25 on the list The Greatest Date Movies of All Time
KennethDempsey added James Spader, Gina Gershon, Molly Ringwald

Released: 1986

Directed by: Howard Deutch

Pretty in Pink is a 1986 American romantic comedy-drama film about love and social cliques in 1980s American high schools. It is one of John Hughes' films starring Molly Ringwald, and is ...more

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