Top 11 Movies like 10 Things I Hate About You (1999)

Movies similar to 10 Things I Hate About You (1999): The DUFF, Picture This!, She's the Man, It's a Boy Girl Thing, Serendipity, Not Another Teen Movie, She's All That, Prom, The Jerk Theory, O, Whatever It Takes.

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The DUFF (2015)

Bianca (Mae Whitman) is a content high school senior whose world is shattered when she learns the student body knows her as 'The DUFF' (Designated Ugly Fat Friend) to her prettier, more popular friends. Now, despite the words of caution from her favorite teacher, she puts aside the potential distraction of her crush, Toby, and enlists Wesley, a slick but charming jock, to help reinvent herself.

Picture This! (2008)

Rich, handsome team captain Drew Patterson, like his elder brothers before, the high school's dream prince, tires of the haughty head cheerleader and shows some interest in nerdy nobody Mandy Gilbert. For her, his invitation to the party of the year of his parental estate bodes instant social promotion, but her overprotective pa Tom grounds her for dishonesty. She's as determined to get in anyway with friends' help as her rival's pack to prevent that and d...

She's the Man (2006)

Viola Johnson (Amanda Bynes) is in a real jam. Complications threaten her scheme to pose as her twin brother, Sebastian, and take his place at a new boarding school. She falls in love with her handsome roommate, Duke, who loves beautiful Olivia, who has fallen for Sebastian! As if that were not enough, Viola's twin returns from London ahead of schedule but has no idea that his sister has already replaced him on campus.

It's a Boy Girl Thing (2006)

Pretty teen girl Nell (Samaire Armstrong) is extremely bookish and can't wait to move on to higher education, while her dim-witted neighbor and classmate, Woody (Kevin Zegers), wants nothing more than to play football. When a class trip to a museum places Nell and Woody under an ancient Incan spell, the two awake the next day to find that they've switched bodies. As they cope with their bizarre situation, Nell and Woody realize that they must discover a wa...

Serendipity (2001)

On a magical night when they are in in their 20s, Jonathan (John Cusack) meets Sara (Kate Beckinsale). He finds it love at first sight, but Sara believes in destiny. After 10 years the two -- with 3,000 miles between them -- must decide if fate wants them to be together again. When love feels like magic, it is called destiny; when destiny has a sense of humor, it is serendipity.

Not Another Teen Movie (2001)

At John Hughes High School, the students are the same as just about every other teenager in a teen movie. The popular jock, Jake (Chris Evans), takes a bet from Austin, the cocky blonde guy (Eric Christian Olsen), that he can transform Janey, the pretty ugly girl (Chyler Leigh), into the prom queen before the prom. But two people are trying to stop Jake from succeeding: his evil sister, Catherine, the cruelest girl in school (Mia Kirshner), and Priscilla, ...

She's All That (1998)

High school hotshot Zach Siler (Freddie Prinze Jr.) is the envy of his peers. But his popularity declines sharply when his cheerleader girlfriend, Taylor (Jodi Lyn O'Keefe), leaves him for sleazy reality-television star Brock Hudson (Matthew Lillard). Desperate to revive his fading reputation, Siler agrees to a seemingly impossible challenge. He has six weeks to gain the trust of nerdy outcast Laney Boggs (Rachael Leigh Cook) -- and help her to become the ...

Prom (2011)

For many high-school students, the prom marks the beginning of their transition from teenager to adult. Several intersecting stories unfold as one group of teens prepares for the seminal event. Nova Prescott (Aimee Teegarden) faces a battle of wills when, unexpectedly, she is attracted to the one guy (Thomas McDonell) who stands in the way of her perfect prom. Mei (Yin Chang) and Tyler (De'Vaughn Nixon) each harbor deep secrets, and excitement builds as th...

The Jerk Theory (2009)

The lead singer/guitarist of a high school rock band openly and unapologetically proclaims himself a newly converted jerk; however, the right girl comes along who could change him back to his former sweet self.

O (2001)

Humanity finds a mysterious, obviously artificial, object buried beneath the Lunar surface and, with the intelligent computer H.A.L. 9000, sets off on a quest.

Whatever It Takes (2000)

A modern-day remake of the Cyrano DeBergerac tale.

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