After 20 years, a successful author Henry McCarthy (Polish) returns to his home town to give a commencement speech, only to fall in love with his old crush Scarlet Smith (Ryder) but is asked to the prom by a sexy high school senior Shasta O’Neil (Duff). Henry faces tough decisions which cause him to consider his love for Scarlet who’s the perfect girlfriend, but when Principle Marshall (Chase) give advise on love things start to become hilariously entertaining.