1. 10 Things I Hate About You
Starring Julia Stiles and Heath Ledger, this movie follows the love story of high school student Cameron James, who has a crush on Bianca. In an attempt to get around their strict father’s rules, Bianca tries to set up bad boy Patrick with her sister, Kat. But what happens when Patrick and Kat start falling for each other, and Kat finds out that he was only using her for Cameron’s advantage?
2. Pretty Woman
This 1990 film stars Richard Gere and Julia Roberts and has become a staple for many couples. Roberts went on to win Best Actress at the Golden Globe Awards for her role as Vivian, a call girl on Hollywood Boulevard. In the film, Gere’s character, Edward, pays Vivian to stay with him in his penthouse for a week, and they begin to develop feelings for each other. Can a wealthy businessman and a call girl build a life together, or will society keep them apart?
3. Failure to Launch
Featuring stars such as Matthew McConaughey and Sarah Jessica Parker, Failure to Launch is a witty and laughable film about a bachelor who still lives at home.
Thirty-five-year-old Tripp has casual girlfriends, and when he gets tired of them, he invites them to his place—where they realize he still lives at home and promptly dump him. Paula, an expert in getting men to move out, is hired by Tripp’s parents to fake date him. After a few awkward and laughable moments, real feelings start to develop as they try to maneuver this delicate situation.
4. How to Lose a Guy in 10 Days
Continuing with McConaughey, this film also features Kate Hudson as women’s magazine journalist Andie Anderson, the “How-To” girl. When one of Andie’s friends gets dumped, she is challenged to write a “what not to do” article—but first, she needs to catch a guy.
That’s where Benjamin Barry, played by McConaughey, comes in. Barry is an advertising executive looking to land a big diamond account but needs to understand women better. Barry’s competition sets him up with Andie, and as they fake date, they begin to fall in love.
5. Dear John
This film may require tissues. Dear John is based on a Nicholas Sparks novel and is one of the most underrated rom-coms out there.
Featuring Channing Tatum and Amanda Seyfried, the film follows the story of John Tyree, an American soldier, after he falls for Savannah, a college student on vacation in Charleston. John and Savannah communicate through letters during his deployments, making plans to build a future together when he returns home. However, a series of events make it difficult for the couple to reunite. Will they eventually end up together, or will time and distance keep them apart?
