In 1995, Chris Brander (Ryan Reynolds) is an Obesity high school senior with a lisp, braces, and a "gentle giant" demeanor who secretly has a huge Crush (love) on his classmate and best friend Jamie Palamino (Amy Smart). After confessing his feelings by writing them in Jamie's yearbook, he attends his and Jamie's graduation party. As he returns Jamie's yearbook to her, it is secretly swapped by her despicable ex-boyfriend, Tim (Ty Olsson), who reads the declaration aloud to everyone and humiliates Chris. Jamie doesn't reciprocate his romantic feelings; after they share a brief kiss on the cheek, Tim and the class burst in and humiliate Chris again. While Jamie admonishes them, an enraged Chris tearfully leaves the party, announcing that he will never return and vows to be more successful than everyone else.