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' employer, company CEO KC (Stephen Root), asks Chris to accompany an emerging self-obsessed pop singer named Samantha James (Anna Faris), 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' hometown.