She's the Man(2006)

It's hard enough being the nerdy new guy on campus without also being the new girl on campus, who has fallen for the coolest guy on campus, who is totally obsessed with the most beautiful girl on campus, who is "crushing" on the nerdy new guy on campus. Viola Johnson had her own good reasons for disguising herself as her twin brother Sebastian and enrolling in his place at his new boarding school, Illyria Prep. She was counting on Sebastian being AWOL from school, while he tried to break into the music scene in London. What she didn't count on was falling in love with her hot roommate, Duke, who in turn only has eyes for the beautiful Olivia. Making matters worse, Olivia is starting to fall for Sebastian, who--for reasons Olivia couldn't begin to guess--appears to be the sensitive type of guy she'd always dreamed of meeting. If things weren't complicated enough, the real Sebastian has come back from London two days earlier than expected and arrives on campus having no clue that he's been replaced--by his own twin sister.