Ryan Gosling made women around the country swoon when he romanced Rachel McAdams in this 2004 flick based on the popular Nicholas Sparks novel about a couple who fall in love in the 1940s.
In 1989, audiences fell in love with Meg Ryan and Billy Crystal’s tale of two New Yorkers who fear that having sex would ruin their friendship.
Keira Knightley, Hugh Grant, Liam Neeson and Emma Thompson were among the many stars who appeared in this 2003 ensemble story about Londoners looking for love the month before Christmas.
A Canadian-born, New York City-based book editor (Sandra Bullock) gets engaged to her assistant (Ryan Reynolds) in order to stay in the United States and continue her rise to the top in this 2009 flick.
Declared one of the most quintessential high school movies of all time, Cameron Crowe’s 1989 film centered around Lloyd Dobler’s (John Cusack) pursuit of Diane Court (Ione Skye).
While he’s at home on leave, soldier John (Channing Tatum) falls for conservative college student Savannah (Amanda Seyfried) in this 2010 tearjerker based on the popular Nicholas Sparks novel.
Julia Roberts appears as a prostitute with a heart of gold who finds her prince charming in the form of Richard Gere’s wealthy millionaire client in this 1990 romantic comedy.
After being dumped by his movie star girlfriend (Kristen Bell), Peter (Jason Segel) flies to Hawaii to get his mind off his failed relationship. While there, he falls for hotel receptionist Rachel (Mila Kunis) in this 2008 rom-com.
While the adorable rapping wedding granny may have been a highlight, it was Adam Sander’s romance with Drew Barrymore’s waitress character that made the 1998 comedy really sing. The flick was even adapted into a Broadway musical that ran for eight months in 2006.
In the 2002 romance based on the Nicholas Sparks bestseller, Landon (Shane West) falls for Jamie (Mandy Moore) only to find out Jamie is stricken with terminal leukemia. and has stopped responding to her treatment. In their final days together, Landon helps Jamie live life to the fullest, crossing off amazing items from her bucket list.
John Hughes’ 1986 Brat Pack film followed high schoolers (played by Molly Ringwald, Andrew McCarthy and Jon Cryer, among others) preparing to go to senior prom.
In 2003, Ashton Kutcher and Brittany Murphy played a young married couple who realize they may be in over their heads while honeymooning in Europe.
When Julia Roberts’ BFF (played by Dermot Mulroney) falls in love with another woman (Cameron Diaz) and is ready to walk down the aisle, she hatches a plan to distract Mulroney’s character Mike so he’ll fall for her instead.
Tired of being in complicated relationships, GQ creative director Dylan (Justin Timberlake) and head hunter Jamie (Mila Kunis) decide to forge a strictly-physical relationship. Emma Stone, Woody Harrelson, Andy Samberg and Jenna Elfman costar in the flick, released in 2011.
Drew Barrymore brought geeky Josie “Grossie” to life in the flick that followed a socially awkward newspaper editor as she went undercover at a high school who fell for her English teacher (Michael Vartan).
Political consultant Will (Ryan Reynolds) attempts to explain his impending divorce and past relationships to his 11-year-old daughter (Abigail Breslin). The 2008 film costars Rachel Weisz, Isla Fisher and Elizabeth Banks.
In 2001, Jennifer Lopez’s character fell — literally! — for a handsome doctor (Matthew McConaughey). The only hitch? He’s already engaged to her biggest client Fran (Bridgette Wilson) and she’s in chrage of planning the ceremony.
One of Woody Allen’s most lauded films, the 1977 romantic comedy won four Academy Awards including Best Picture. Directing and starring in the flick, Allen plays Alvy Singer, a comedian trying to maintain his relationship with Annie (Diane Keaton). Paul Simon, Shelley Duvall and Christopher Walken costar.
Tasked with writing an article about how to ditch a man in less than two weeks, Andie Anderson (Kate Hudson) quickly strikes up a relationship with ad exec Benjamin Barry (Matthew McConaughey) in this 2003 rom-com.
In 2010, Miley Cyrus played a rebellious teen who’s shipped to a Southern beach town to spend the summer with her father Steve (Greg Kinnear). While there, she falls hard for Will (Liam Hemsworth), who encourages her to be kinder to her ailing dad.
Always a bridesmaid, never a bride — that’s the story of Jane Nichols’ (Katherine Heigl) life in this 2008 film. When reporter Kevin Doyle (James Marsden) agrees to cover Jane’s sister’s wedding, he stumbles upon Jane’s day planner and decides to make her the focus of his story.
Reese Witherspoon poured on the good girl charm appearing opposite Patrick Dempsey as an engaged New York woman who returns to Alabama to beg her first husband (Josh Lucas) for a divorce.
Renee Zellweger stars as a self-deprecating British woman who is determined to improve her love life. Colin Firth and Hugh Grant play her vastly different love interests.
Tom Hanks and Meg Ryan strike up a romance over e-mail and then stumble upon each other by chance in Nora Ephron’s 1998 romantic comedy.
Ashton Kutcher, Jessica Alba, Bradley Cooper and Julia Roberts were among the legion of stars who appeared in this ensemble comedy about Los Angelenos whose lives intersect on February 14.
In 1999, soccer player Zack Siler (Freddie Prinze Jr.) was challenged to transform an unattractive high school student (Rachel Leigh Cook) into the school’s prom queen.
Ben Stiller made his directorial debut in this 1994 cult classic costarring Winona Ryder, Ethan Hawke and Stiller. Produced on a $11.5 million budget, the flick documented Ryder’s character Lelaina’s quest to film a documentary about the lives of her three roommates (Hawke, Janeane Garofalo and Steve Zahn).
Directed by Steve Rash, the 1987 teen film stars Patrick Dempsey as a high school nerd who pays a popular cheerleader (Amanda Peterson) $1,000 to pretend to be his girlfriend for a month.
Shakespeare’s The Taming of the Shrew was revived in this teen comedy costarring Heath Ledger, Julia Stiles and Joseph Gordon-Levitt. In the film — which served as a breakout role for Ledger and Stiles — Kat (Stiles) falls for Patrick (Ledger), unaware that he was being paid to date her.
When Theresa (Robin Wright) stumbles upon a tragic love letter in a bottle on the beach, she is determined to track down its author. The 1999 film also stars Kevin Costner and Paul Newman.