In 1995, Chris Brander is an overweight high school senior who secretly has a huge romantic crush on his classmate and best friend Jamie Palamino. 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, 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.
In 2005, Chris has lost weight, is handsome, lives in Los Angeles; and is a womanizer and a highly successful record producer. Prior to Christmas, Chris's employer, company CEO KC, asks Chris to accompany an emerging self-obsessed pop singer named Samantha James, whom Chris once went out with and ended up in the hospital afterwards, to Paris to ensure she signs with their label, an order to which Chris reluctantly complies. During the trip to Paris, Samantha accidentally sets her private jet on fire resulting in an emergency landing in New Jersey, near Chris's hometown.
