Down to You (2000)

A young man wins and loses the first serious love of his life. Al Connelly falls in love with the girl of his dreams. After the summer she breaks up with him. As he tries to recover Al goes to desperate measures.

Director: Kris Isacsson

Cast: Freddie Prinze Jr., Julia Stiles, Selma Blair, Shawn Hatosy, Zak Orth, Ashton Kutcher, Rosario Dawson, Henry Winkler, Lucie Arnaz, Lauren German, Zay Harding, Amanda Barfield, Chloe Hunter, Granger Green, Jed Rhein, Joseff Stevenson, Bradley Pierce, Elizabeth Levin