1. She's All That
   Pretty Woman
2. Sex and the City
   40 Days and 40 Nights

Pretty Woman was released on March 23, 1990. It was directed by Garry Marshall and brought in more than $463 million at the box office!

1. Just Friends
   Hitch
2. 40 Days and 40 Nights
   The Proposal

Starring Sandra Bullock and Ryan Reynolds, The Proposal was released on June 1, 2009. The film was written Peter Chiarelli and directed by Anne Fletcher.

1. Just Friends
   10 Things I Hate About You
2. Never Been Kissed
   The Wedding Planner

10 Things I Hate About You was released on March 31, 1999. It starred actors Julia Stiles and the late Heath Ledger.

1. Leap Year
   The Wedding Singer
2. She's Out of My League
   When in Rome

The Wedding Singer was written by Tim Herlihy and directed by Frank Coraci. It starred Adam Sandler as a wedding singer in the 1980s and Drew Barrymore as a waitress with whom he falls in love.

1. Say Anything…
   Knocked Up
2. Pretty in Pink
   Just Married

Knocked Up was released on June 1, 2007 to box office success, grossing $219 million worldwide! It was directed by Judd Apatow and starred Seth Rogen and Katherine Heigl.

1. Definitely, Maybe
   Serendipity
2. How to Lose a Guy in 10 Days
   50 First Dates

Based on a short cartoon book by the same name, How to Lose a Guy in 10 Days was a 2003 romantic comedy that brought in more than $177 million at the box office.

1. Sweet Home Alabama
   Six Days Seven Nights
2. When Harry Met Sally...
   Never Been Kissed

When Harry Met Sally... is one of the top romantic comedies of all time! The story was written by Nora Ephron and the film, which starred Billy Crystal and Meg Ryan, was directed by Rob Reiner.

1. Confessions of a Shopaholic
   Maid in Manhattan
2. Sex and the City
   Six Days Seven Nights

Based on the television series, Sex and the City, Director Michael Patrick King took the story to the big screen in 2008. The film was 2 hours and 25 minutes and starred the original crew of Carrie, Miranda, Charlotte and Samantha.

1. No Strings Attached
   Just Married
2. The Heartbreak Kid
   Sweet Home Alabama

What do you get when you pair up Ashton Kutcher and Natalie Portman? A box office hit! No Strings Attached was released on January 11, 2011 and brought in more than $149 million.

1. Leap Year
   When Harry Met Sally...
2. 50 First Dates
   Maid in Manhattan

Adam Sandler and Drew Barrymore pair up in this 2004 romantic comedy. The film as directed by Peter Segal and was filmed mostly on the Hawaiian island of Oahu.

1. 27 Dresses
   No Reservations
2. Music and Lyrics
   Leap Year

Starring Katherine Heigl and James Marsden, 27 Dresses was released January 18, 2008 in the United states. It was directed by Anne Fletcher.

1. When in Rome
   Hitch
2. The Break-Up
   Just Married

Earning more than $205 million at the box office, The Break-Up was directed by Peyton Reed and produced by Vince Vaughn, Scott Stuber and Peter Billingsley. It was referred to as an "anti-romantic" comedy by Rotten Tomatoes.

1. Just Go with It
   50 First Dates
2. Life as We Know It
   She's All That

Did you know that Just Go with It was based on the 1969 film titled Cactus Flower? It was produced by Adam Sandler, Jack Giarraputo and Heather Parry, and musician Dave Matthews even had a small role!

1. She's All That
   Sweet Home Alabama
2. 40 Days and 40 Nights
   Hitch

Sweet Home Alabama was directed by Andy Tennant and starred Reese Witherspoon, Josh Lucas, Patrick Dempsey and Candice Bergen. The film was released by Touchstone Pictures on September 27, 2002.

1. Maid in Manhattan
   When in Rome
2. Just Married
   Pretty in Pink

Jennifer Lopez landed the lead role as Marisa Ventura in this 2002 romantic comedy. Maid in Manhattan earned more than $154 million at the box office.

1. Just Married
   The Break-Up
2. She's Out of My League
   The Heartbreak Kid

She's Out of My League was born on March 12, 2010. Main character Kirk Kettner is portrayed by actor Jay Baruchel, who also appeared in Knocked Up and Tropic Thunder.

1. Serendipity
   27 Dresses
2. She's All That
   Sweet Home Alabama

Serendipity was release on October 5, 2001. It was directed by Peter Chelsom and featured John Cusack as Jonathan Trager and Kate Beckinsale as Sara Thomas.

1. The Break-Up
   Hitch
2. Sex and the City
   He's Just Not That Into You

Need some professional dating advice? Call Alex Hitchens! Will Smith portrayed Hitch in this 2005 romantic comedy. The film also featured actors Eva Mendes, Kevin James and Amber Valletta.

1. Maid in Manhattan
   27 Dresses
2. Serendipity
   Music and Lyrics

Starring Hugh Grant and Drew Barrymore, Music and Lyrics was released on February 14, 2007. As a Valentine's Day release, this film grossed more than $145 million at the box office.

1. The Wedding Planner
   What Happens in Vegas
2. How to Lose a Guy in 10 Days
   Knocked Up

Jennifer Lopez and Matthew McConaughey paired up for this romantic comedy in 2001. Directed by Adam Shankman, The Wedding Planner grossed just about $95 million at the box office.

1. Never Been Kissed
   Pretty in Pink
2. No Reservations
   40 Days and 40 Nights

Never Been Kissed was a 1999 romantic comedy directed by Raja Gosnell, and starred Drew Barrymore, David Arquette, Michael Vartan, Leelee Sobieski, Jeremy Jordan, Molly Shannon, Garry Marshall, John C. Reilly and James Franco.

1. The Wedding Planner
   Pretty in Pink
2. What Happens in Vegas
   Going the Distance

Based on the catchphrase "What happens in Vegas, stays in Vegas," this film was released on May 9, 2008. It brought in more than $219 million at the box office and starred Cameron Diaz and Ashton Kutcher.

1. Knocked Up
   Six Days Seven Nights
2. The Proposal
   The Break-Up

Six Days, Seven Nights was directed by Ivan Reitman and featured Harrison Ford and Anne Heche. It was filmed on location in Kauai, and released on June 12, 1998.

1. Pretty in Pink
   Leap Year
2. Confessions of a Shopaholic
   Just Go with It

Molly Ringwald was born on February 18, 1968. Her first major role was that of Molly on the NBC sitcom The Facts of Life in 1979. She landed the role of Andie Walsh in Pretty in Pink in 1986.

1. Life as We Know It
   The Heartbreak Kid
2. The Wedding Planner
   Confessions of a Shopaholic

Life As We Know It was a 2010 romantic comedy-drama film directed by Greg Berlanti, starring Katherine Heigl and Josh Duhamel. It was released on October 8, 2010 and brought in more than $105 million at the box office!

1. Knocked Up
   No Reservations
2. Sweet Home Alabama
   Leap Year

No reservations? No problem! Catherine Zeta-Jones and Aaron Eckhart took to the big screen in 2007 with this romantic comedy. The film earned more than $92 million at the box office!

1. Hitch
   Never Been Kissed
2. Leap Year
   Just Friends

Just Friends was directed by Roger Kumble, written by Adam "Tex" Davis and starred Ryan Reynolds, Amy Smart, Anna Faris, Chris Klein and Christopher Marquette. It was released on November 23, 2005 and made just $50 million at the box office.

1. Never Been Kissed
   Definitely, Maybe
2. The Break-Up
   No Reservations

Definitely, Maybe was a 2008 romantic comedy-drama film written and directed by Adam Brooks. It starred Ryan Reynolds, Isla Fisher, Rachel Weisz, Elizabeth Banks, Abigail Breslin, and Kevin Kline!

1. Pretty in Pink
   Pretty Woman
2. What Happens in Vegas
   Confessions of a Shopaholic

Based on the Shopaholic series of novels written by Sophie Kinsella, Confessions of a Shopaholic was released on February 13, 2009. It featured Isla Fisher in the leading role of Rebecca Bloomwood.

1. Six Days Seven Nights
   Say Anything…
2. 27 Dresses
   Valentine's Day

Valentine's Day was released on February 12, 2010. It featured an ensemble cast led by Jessica Alba, Kathy Bates, Jessica Biel, Bradley Cooper, Eric Dane, Patrick Dempsey, Héctor Elizondo, Jamie Foxx, Jennifer Garner, Topher Grace, Anne Hathaway, Ashton Kutcher, Queen Latifah, Taylor Lautner, George Lopez, Shirley MacLaine, Emma Roberts, Julia Roberts, Carter Jenkins and Taylor Swift.

1. Going the Distance
   She's Out of My League
2. Definitely, Maybe
   He's Just Not That Into You

Oh, the phrase that helped so many women get over troubled relationships! This film had an all-star cast of the following actors: Ben Affleck, Jennifer Aniston, Drew Barrymore, Jennifer Connelly, Kevin Connolly, Bradley Cooper, Ginnifer Goodwin, Scarlett Johansson and Justin Long!

1. Say Anything…
   Just Go with It
2. How to Lose a Guy in 10 Days
   When in Rome

When in Rome was directed by Mark Steven Johnson, and co-written by Johnson, David Diamond and David Weissman. The film stars Kristen Bell and Josh Duhamel and was released by Touchstone Pictures on January 29, 2010.

1. 40 Days and 40 Nights
   Six Days Seven Nights
2. She's All That
   Going the Distance

She's All That lead character Zack Siler was portrayed by actor Freddie Prinze Jr. He is on the hunt to woo dorky Laney Boggs portrayed by Rachel Leigh Cook.

1. The Heartbreak Kid
   Confessions of a Shopaholic
2. The Break-Up
   Leap Year

Did you know that The Heartbreak Kid of 2007 was a remake of a 1972 film of the same name? The 2007 version starred Ben Stiller as Eddie Cantrow.

1. Serendipity
   Leap Year
2. Maid in Manhattan
   Confessions of a Shopaholic

Leap Year was a 2010 romantic comedy film directed by Anand Tucker. It featured Amy Adams and Matthew Goode in the leading roles of Anna Brady and Declan O'Callaghan.

1. How to Lose a Guy in 10 Days
   27 Dresses
2. Sweet Home Alabama
   Going the Distance

Drew Barrymore paired up with Justin Long in this 2010 romantic comedy. Barrymore's character Erin Rankin Langford attempts to 'go the distance' with Long's character Garrett Scully.

1. When in Rome
   Pretty in Pink
2. Just Married
   Say Anything…

Ashton Kutcher is no stranger to romantic comedies. In this film, Just Married, he pairs up with Brittany Murphy and stars as Tom Leezak. The film was made on just an $18 million budget and grossed $101 million at the box office.

1. Just Go with It
   The Break-Up
2. When in Rome
   A Lot Like Love

A Lot Like Love was a 2005 romantic comedy-drama film directed by Nigel Cole. Lead characters Oliver Martin and Emily Friehly were portrayed by actors Ashton Kutcher and Amanda Peet.

1. Going the Distance
   Maid in Manhattan
2. Say Anything…
   Pretty in Pink

John Cusack was born on June 28, 1966 in Evanston, Illinois. He played the leading male role, not just in Say Anything... but also The Sure Thing, Better Off Dead and The Journey of Natty Gann to name a few.

1. He's Just Not That Into You
   No Strings Attached
2. 40 Days and 40 Nights
   Knocked Up

40 Days and 40 Nights featured Josh Hartnett in the lead role of Matt Sullivan. Did you know that Hartnett made his debut in the 1997 TV series Cracker?