Are you looking for a great movie to watch tonight? Check out our list of the 30 best dating movies of all time!
These films are sure to get you in the mood for love. From funny comedies to heartwarming romances, we’ve got something for everyone. So grab some popcorn and settle in for a night of entertainment!
30 Best Dating Movies
To make your search a little easier, we’ve compiled a list of the 30 best dating movies of all time. Whether you’re looking for a classic rom-com or a tearjerker, everyone has something on this list.
So grab some popcorn and get ready to curl up with your special someone for a night of romantic movie watching.
Here are the 30 best dating movies of all time:
The Notebook
A classic romantic drama, The Notebook tells the story of Noah and Allie, two young lovers who World War II separates.
Despite the odds, the two eventually find their way back to each other and spend the rest of their lives together.
If you’re looking for a movie that will make you believe in true love, this is the one for you.
Directed by: Nick Cassavetes
Starring: Ryan Gosling, Rachel McAdams, James Garner
Release date: June 25, 2004 (United States)
Runtime: 124 minutes
Sleepless in Seattle
Sleepless in Seattle is a classic rom-com starring Tom Hanks and Meg Ryan. The movie follows Sam, a widower who moves to Seattle with his son in hopes of finding love again.
Along the way, Sam meets Annie, a woman who falls in love with him despite never having met him in person.
If you’re looking for a heartwarming and hilarious movie about love, this is the one for you.
Directed by: Nora Ephron
Starring: Tom Hanks, Meg Ryan, Bill Pullman
Release date: June 24, 1993 (United States)
Runtime: 105 minutes
When Harry Met Sally
When Harry Met Sally is a classic rom-com that follows the story of two friends who eventually fall in love, the movie explores whether or not men and women can ever really be “just friends.”
If you’re looking for a funny and romantic movie, this is the one for you.
Directed by: Rob Reiner
Starring: Billy Crystal, Meg Ryan, Carrie Fisher
Release date: July 21, 1989 (United States)
Runtime: 96 minutes
Pretty Woman
Pretty Woman is a classic romantic comedy starring Julia Roberts and Richard Gere. The movie follows Vivian, a prostitute who is hired by Edward, a wealthy businessman, to be his escort for a week.
The two eventually fall in love with each other, and Vivian is able to turn her life around.
If you’re looking for a funny and romantic movie, this is the one for you.
Directed by: Garry Marshall
Starring: Julia Roberts, Richard Gere, Hector Elizondo
Release date: March 23, 1990 (United States)
Runtime: 119 minutes
The Fault in Our Stars
The Fault in Our Stars is a young adult romance novel turned movie. The story follows Hazel, a teenage girl with cancer, who falls in love with Augustus, another teenager with cancer.
Despite the tragic circumstances, the two are able to find happiness with each other.
If you’re looking for a romantic and tear-jerking movie, this is the one for you.
Directed by: Josh Boone
Starring: Shailene Woodley, Ansel Elgort, Willem Dafoe
Release date: June 06, 2014 (United States)
Runtime: 126 minutes
Love Story
Love Story is a classic romantic drama starring Ali MacGraw and Ryan O’Neal. The movie follows the story of Jenny, a wealthy girl from a privileged background, and Oliver, a working-class student at Harvard.
Despite their different upbringings, the two falls in love with each other and must fight to stay together.
If you’re looking for a movie that will make you believe in true love, this is the one for you.
Directed by: Arthur Hiller
Starring: Ali MacGraw, Ryan O’Neal, John Marley
Release date: December 16, 1970 (United States)
Runtime: 96 minutes
The Princess Bride
The Princess Bride is a classic romantic comedy starring Cary Elwes and Robin Wright. The movie follows the story of Buttercup, a beautiful young woman who is kidnapped and taken away to marry Prince Humperdinck.
Fortunately, her true love Westley comes to rescue her, and the two ride off into the sunset together.
If you’re looking for a funny and romantic movie, this is the one for you.
Directed by: Rob Reiner
Starring: Cary Elwes, Robin Wright, Mandy Patinkin
Release date: September 25, 1987 (United States)
Runtime: 98 minutes
Say Anything
Say Anything is a classic romantic comedy starring John Cusack and Ione Skye. The movie follows the story of Lloyd, an underachiever who falls in love with Diane, the valedictorian of their high school.
Lloyd must then fight to win her over and prove that he is worthy of her love.
If you’re looking for a sweet and romantic movie, this is the one for you.
Directed by: Cameron Crowe
Starring: John Cusack, Ione Skye, John Mahoney
Release date: April 14, 1989 (United States)
Runtime: 100 minutes
Never Been Kissed
Never Been Kissed is a romantic comedy starring Drew Barrymore and Michael Vartan. The movie follows the story of Josie, a journalist who goes undercover at a high school to write an article about the teenage experience.
Josie ends up falling in love with her English teacher and must choose between the man she loves and the life she wants.
If you’re looking for a funny and romantic movie, this is the one for you.
Directed by: Raja Gosnell
Starring: Drew Barrymore, Michael Vartan, David Arquette
Release date: April 09, 1999 (United States)
Runtime: 103 minutes
You’ve Got Mail
You’ve Got Mail is a romantic comedy starring Tom Hanks and Meg Ryan. The movie follows the story of two people who fall in love with each other online, without knowing that they are actually business rivals.
If you’re looking for a sweet and romantic movie, this is the one for you.
Directed by: Nora Ephron
Starring: Tom Hanks, Meg Ryan, Greg Kinnear
Release date: December 18, 1998 (United States)
Runtime: 119 minutes
The Holiday
The Holiday is a romantic comedy starring Cameron Diaz and Kate Winslet. The movie follows the story of two women who swap homes for the holidays in order to get away from their exes.
While they are both on holiday, they end up falling in love with two different men.
If you’re looking for a funny and romantic movie, this is the one for you.
Directed by: Nancy Meyers
Starring: Cameron Diaz, Kate Winslet, Jude Law, Jack Black
Release date: December 08, 2006 (United States)
Runtime: 138 minutes
How to Lose a Guy in Ten Days
How to Lose a Guy in Ten Days is a romantic comedy starring Kate Hudson and Matthew McConaughey. The movie follows the story of Andie, a journalist who must write an article on how to lose a guy in ten days.
In order to do this, she starts dating Ben and tries to drive him away. However, she ends up falling in love with him instead.
If you’re looking for a funny and romantic movie, this is the one for you.
Directed by: Donald Petrie
Starring: Kate Hudson, Matthew McConaughey, Adam Goldberg, Kathryn Hahn
Release date: February 07, 2003 (United States)
Runtime: 116 minutes
The Proposal
The Proposal is a romantic comedy starring Sandra Bullock and Ryan Reynolds. The movie follows the story of Margaret, a publishing executive who forces her assistant Andrew to marry her so she can stay in the country.
However, after spending time together, the two start to fall for each other and Margaret must decide if she wants to go through with the marriage or not.
If you’re looking for a funny and romantic movie, this is the one for you.
Directed by: Anne Fletcher
Starring: Sandra Bullock, Ryan Reynolds, Betty White, Denis O’Hare
Release date: June 19, 2009 (United States)
Runtime: 108 minutes
27 Dresses
27 Dresses is a romantic comedy starring Katherine Heigl and James Marsden. The movie follows the story of Jane, a woman who has been a bridesmaid 27 times.
When her sister gets engaged to the man Jane loves, she starts to question her own life and what she really wants.
If you’re looking for a funny and romantic movie, this is the one for you.
Directed by: Anne Fletcher
Starring: Katherine Heigl, James Marsden, Malin Akerman, Edward Burns
Release date: January 18, 2008 (United States)
Runtime: 111 minutes
Yes Man
Yes Man is a romantic comedy starring Jim Carrey and Zooey Deschanel. The movie follows the story of Carl, a man who decides to say “yes” to everything that comes his way.
As a result, he meets a woman named Allison and falls in love with her. However, things start to go wrong when Carl’s new lifestyle starts to take over his life.
If you’re looking for a funny and romantic movie, this is the one for you.
Directed by: Peyton Reed
Starring: Jim Carrey, Zooey Deschanel, Terence Stamp, Bradley Cooper
Release date: December 19, 2008 (United States)
Runtime: 104 minutes
He’s Just Not That Into You
He’s Just Not That Into You is a romantic comedy starring Jennifer Aniston and Ben Affleck. The movie follows the story of a group of friends who are all looking for love.
However, as they start to date different people, they realize that love is not always easy to find.
If you’re looking for a funny and romantic movie, this is the one for you.
Directed by: Ken Kwapis
Starring: Jennifer Aniston, Ben Affleck, Drew Barrymore, Scarlett Johansson
Release date: February 06, 2009 (United States)
Runtime: 129 minutes
The Ugly Truth
The Ugly Truth is a romantic comedy starring Katherine Heigl and Gerard Butler. The movie follows the story of Abby, a TV producer who is trying to find love.
In order to do this, she hires Mike, a womanizing expert, to help her. However, she soon realizes that she may have more feelings for him than she originally thought.
If you’re looking for a funny and romantic movie, this is the one for you.
Directed by: Robert Luketic
Starring: Katherine Heigl, Gerard Butler, Bree Turner, Eric Winter
Release date: July 24, 2009 (United States)
Runtime: 96 minutes
What Happens in Vegas
What Happens in Vegas is a romantic comedy starring Cameron Diaz and Ashton Kutcher. The movie follows the story of two people who get married after a night of drunkenness in Las Vegas.
However, when they wake up, they realize that they don’t actually know each other. They then have to decide whether to stay married or get divorced.
If you’re looking for a funny and romantic movie, this is the one for you.
Directed by: Tom Vaughan
Starring: Cameron Diaz, Ashton Kutcher, Rob Corddry, Lake Bell
Release date: May 23, 2008 (United States)
Runtime: 99 minutes
The Time Traveler’s Wife
The Time Traveler’s Wife is a romantic drama starring Eric Bana and Rachel McAdams. The movie follows the story of Clare and Henry, a couple who are in love with each other despite the fact that Henry has a rare condition that causes him to time travel.
Clare has to deal with the fact that she never knows when or where her husband will disappear to.
If you’re looking for a heart-warming and romantic movie, this is the one for you.
Directed by: Robert Schwentke
Starring: Eric Bana, Rachel McAdams, Arliss Howard, Ron Livingston
Release date: August 14, 2009 (United States)
Runtime: 107 minutes
Leap Year
Leap Year is a romantic comedy starring Amy Adams and Matthew Goode. The movie follows the story of Anna, a woman who is planning to propose to her boyfriend on Leap Day.
However, when he cancels their trip to Ireland, she decides to go by herself. On the way, she meets a man named Declan, and they end up falling for each other.
If you’re looking for a funny and romantic movie, this is the one for you.
Directed by: Anand Tucker
Starring: Amy Adams, Matthew Goode, Adam Scott, John Lithgow
Release date: January 08, 2010 (United States)
Runtime: 100 minutes
500 Days of Summer
500 Days of Summer is a romantic drama starring Zooey Deschanel and Joseph Gordon-Levitt. The movie follows the story of Tom, a man who falls in love with a woman named Summer.
However, even though they have a great relationship, Summer does not believe in love, and she eventually breaks up with him.
If you’re looking for a heart-warming and romantic movie, this is the one for you.
Directed by: Marc Webb
Starring: Zooey Deschanel, Joseph Gordon-Levitt, Geoffrey Arend, Chloe Moretz
Release date: July 17, 2009 (United States)
Runtime: 95 minutes
Crazy, Stupid, Love
Crazy, Stupid, Love. is a romantic comedy starring Steve Carell and Ryan Gosling. The movie follows the story of Cal, a man who is going through a divorce.
In order to get over his wife, he asks his young friend Jacob to teach him how to pick up women. However, he soon realizes that he may be falling for someone else.
If you’re looking for a funny and romantic movie, this is the one for you.
Directed by: Glenn Ficarra and John Requa
Starring: Steve Carell, Ryan Gosling, Julianne Moore, Emma Stone
Release date: July 29, 2011 (United States)
Runtime: 118
Think Like A Man
Think Like A Man is a romantic comedy starring Michael Ealy and Meagan Good. The movie follows the story of four men who are looking for love.
However, they soon realize that they need to change their ways in order to find the right woman.
If you’re looking for a funny and romantic movie, this is the one for you.
Directed by: Tim Story
Starring: Michael Ealy, Meagan Good, Kevin Hart, Taraji P. Henson
Release date: April 20, 2012 (United States)
Runtime: 122 minutes
Love Don’t Cost a Thing
Love Don’t Cost a Thing is a romantic comedy starring Nick Cannon and Christina Milian. The movie follows the story of a teenage boy named Alvin who falls for a girl named Paris.
However, she is only interested in dating rich guys. In order to win her over, he pretends to be someone he’s not.
If you’re looking for a funny and romantic movie, this is the one for you.
Directed by: Troy Beyer
Starring: Nick Cannon, Christina Milian, Kenan Thompson, Kal Penn
Release date: December 16, 2003 (United States)
Runtime: 97 minutes 25. The Notebook
How To Be Single
How to Be Single is a romantic comedy starring Dakota Johnson and Rebel Wilson. The movie follows the story of Alice, a woman who is fresh out of a long-term relationship.
She decides to move to New York City in order to figure out what she wants in life. Along the way, she meets a lot of different people and has many different experiences.
If you’re looking for a funny and romantic movie, this is the one for you.
Directed by: Christian Ditter
Starring: Dakota Johnson, Rebel Wilson, Leslie Mann, Alison Brie
Release date: February 12, 2016 (United States)
Runtime: 109 minutes
Ghosts of Girlfriends Past
Ghosts of Girlfriends Past is a romantic comedy starring Matthew McConaughey and Jennifer Garner. The movie follows the story of Connor, a man who is haunted by the ghosts of his past girlfriends.
These ghosts show him all of the ways that he has messed up in relationships in the past. However, they also help him to realize that he needs to change his ways if he ever wants to find true love.
If you’re looking for a funny and romantic movie, this is the one for you.
Directed by: Mark Waters
Starring: Matthew McConaughey, Jennifer Garner, Lacey Chabert, Christina Milian
Release date: May 01, 2009 (United States)
Runtime: 103 minutes
Love Happens
Love Happens is a romantic comedy starring Aaron Eckhart and Jennifer Aniston. The movie follows the story of Burke, a self-help author who falls for a florist named Eloise.
However, he soon realizes that he needs to deal with his own issues before he can truly be in a healthy relationship.
If you’re looking for a funny and romantic movie, this is the one for you.
Directed by: Brandon Camp
Starring: Aaron Eckhart, Jennifer Aniston, Dan Fogelman, Judy Greer
Release date: September 18, 2009 (United States)
Runtime: 108 minutes
50 First Dates
50 First Dates is a romantic comedy starring Adam Sandler and Drew Barrymore. The movie follows the story of Henry, a man who falls for a woman named Lucy.
However, there’s one problem: she has short-term memory loss and forgets about him every day. So he has to find new and creative ways to make her fall in love with him all over again.
If you’re looking for a funny and romantic movie, this is the one for you.
Directed by: Peter Segal
Starring: Adam Sandler, Drew Barrymore, Rob Schneider, Sean Astin
Release date: February 13, 2004 (United States)
Runtime: 99 minutes
13 Going On 30
13 Going on 30 is a romantic comedy starring Jennifer Garner and Mark Ruffalo. The movie follows the story of Jenna, a 13-year-old girl who wishes she was 30.
Her wish comes true and she suddenly finds herself in the body of her 30-year-old self. However, she soon realizes that being an adult isn’t always as great as it seems.
If you’re looking for a funny and romantic movie, this is the one for you.
Directed by: Gary Winick
Starring: Jennifer Garner, Mark Ruffalo, Judy Greer, Andy Serkis
Release date: April 23, 2004 (United States)
Runtime: 97 minutes
Hitch
Hitch is a romantic comedy starring Will Smith and Eva Mendes. The movie follows the story of Alex, a “date doctor” who helps men to improve their dating skills.
However, he soon finds himself in need of help when he falls for a woman named Sara.
If you’re looking for a funny and romantic movie, this is the one for you.
Directed by: Andy Tennant
Starring: Will Smith, Eva Mendes, Kevin James, Amber Valletta
Release date: February 11, 2005 (United States)
Runtime: 118 minutes
Conclusion
All of the movies listed above are perfect for a fun and romantic night. Whether you’re looking for a laugh or to feel all the feels, these films will do the trick. So pop some popcorn, get cozy on the couch, and enjoy!
