 A modern-day version of the Cyrano De Bergeac tale in which geekish high school student Ryan Woodman (Shane West), likes the popular Ashley Grant (Jodi Lynn O Keefe), but does not have the nerve to express his feelings for her. Ashley s cousin, football jock Chris Campbell (James Franco), coaches Ryan on courting Ashley in exchange for Ryan giving him help on how to win the heart of Ryan s platonic next-door neighbor Maggie Carter (Marla Sokoloff) in time for the senior prom which has the doomed ship  Titanic  as its theme.