Plot: Late-twenty-something Chris Brander is a good looking, successful Los Angeles based recording executive, who can have his choice of almost any woman he wants. This has not always been the case, as he was an overweight geek in high school in small town New Jersey. At the time, he was in love with his best friend, Jamie Palomino, who said she loved him... like a brother, when he finally professed his love to her. Being a cheerleader, she was one of the popular kids and seemed only to date good looking guys, all who ended up being jerks. His experience with Jamie has led to Chris having a theory of dating, the basic tenet being not to fall into the "friend" zone with someone you want to date, a zone of which one cannot get out. Jamie was also his impetus to turn his life around, to get fit and make a success out of his life. In the lead up to Christmas, he is on his way to Paris with the current Hollywood "it" girl, Samantha James, who his boss KC wants Chris to woo so that they can sign her when she makes her foray into music. In reality, she is talentless, vacuous and totally self-absorbed, which Chris knows, but Samantha sees Chris as her Christmas present, he to attend to her every need and want on this trip, sexual or otherwise. Their flight hits technical problems forcing an unscheduled stop in New Jersey, where Chris has not been since he ran away ten years ago following high school. Back in his home town, Chris runs into many old friends and acquaintances, including Jamie. He finds that he is still in love with her, and is determined not to fall back into the "friend" zone with her, which is easier said than done. Other obstacles to a Chris/Jamie happy ending are Samantha, who will not be ignored by Chris, and Dusty Dinkleman, another geek admirer of Jamie's in high school who too has turned his life around as a paramedic and whose intention is to out-woo Chris for Jamie's affections.
Alternative Plot: High school student Chris Brander (Ryan Reynolds) loves his best friend, Jamie Palamino (Amy Smart). He finally confesses his feelings, but she tells him that she just wants to be friends, and he leaves town in shame. Ten years later, Chris is a successful record executive and involved with self-absorbed pop star Samantha James (Anna Faris). He still pines for Jamie, though, and when his plans to go to Paris for the holidays fall through, he returns to his hometown to try and win her heart.
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