Stay Cool (2009)

After 20 years, bestselling author Henry McCarthy (Mark Polish) returns to his home town, only to fall in love with his old crush Scarlet Smith (Winona Ryder). Things become complicated when he is asked to the prom by sexy high school senior Shasta O'Neil (Hilary Duff).

Facing some tough decisions about love and life, Henry turns to Principle Marshall (Chevy Chase) f...