In 1995, Chris Brander (Ryan Reynolds) is an overweight high school senior who secretly has a huge romantic crush on his classmate and best friend Jamie Palamino (Amy Smart). After confessing his feelings by writing them in Jamie's yearbook, he attends their 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. Chris tearfully leaves the party, announcing that he will never return and vows to be more successful than everyone else.