Duke from "She's The Man"
Channing Tatum played both of Amanda Bynes' character's love interests in "She's the Man." While posing as a boy, Duke is her roommate at the elite all-boys prep school. However, when he finds out Amanda Bynes's secret, he falls for her as a girl. The whole story is pretty convoluted.
Charlie from "Charlie St. Cloud"
Zac Efron plays the tortured Charlie St. Cloud in this movie. He grapples with his younger brother's death and the guilt that it was possibly his fault. He meets a girl who wants to take him on a sailing trip, which would mean letting go of his brother forever.