- While visiting his hometown during Christmas, a man comes face-to-face with his old high-school crush and best friend--a woman whose rejection of him turned him into a ferocious womanizer.
- Chris Brander has always been friends with Jamie Palamino, but now decides it is time to take his relationship to the next step. The problem is that Jamie still wants to be Just Friends. When he moves to L.A., he becomes an attractive music manager, whom everyone wants. He is flying to Paris with his newest singing sensation Samantha James when their jet catches fire and is forced to land. He ends up back home; to his surprise he re-encounters Jamie--and sets out to be more than Just Friends this time.—Film_Fan
- Late-twentysomething Chris Brander is a good-looking, successful Los Angeles-based recording executive who can have any woman he wants. This hasn't always been the case; he was an overweight geek in high school in small-town New Jersey. Back then he was in love with his best friend, Jamie Palamino; when he finally professed his love for her, she said she loved him like a brother. Being a cheerleader, she was one of the popular kids and seemed to date only good-looking guys--who ended up being jerks. Chris' experience with Jamie has led to him having a theory of dating, the basic tenet being not to fall into the "friend" zone with someone you want to date, because the friend zone is inescapable. Jamie was also his impetus to turn his life around, to get fit and make his life a success. In the lead-up to Christmas, he is on his way to Paris with the current Hollywood "it" girl, Samantha James, whom 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: someone 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 left 10 years ago after high school. Back in his hometown, 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 of Jamie's geek admirer in high school; he has always turned his life around and is a paramedic. His intention is to out-woo Chris for Jamie's affections.—Huggo
- When he confessed his love for his best friend during their high-school years, Chris was met with a broken heart and a degrading humiliation. Only adding insult to injury was his larger-than-life frame, which became a source of ridicule for cruel classmates. But years later, he's now a hotshot record producer in Hollywood, the complete physical opposite of his high-school self. He's also got an up-and-coming act, Samantha James, who has a psychotic crush on her producer. When a freak accident occurs on the way to Paris, Chris is forced to return home with her in tow. Unexpectedly he comes face-to-face with the friend he has tried so desperately to forget. With the chance to woo her again, he will do everything despite his client's violent misgivings and a competitive rival suitor against him. No matter what crazy obstacles he must overcome, Chris will do whatever it takes to be more than just friends.—mystic80/Blueyz413
- Chris Brander (Reynolds), an obese high school student in a suburban community in New Jersey, is in love with his best friend, Jamie Palamino (Smart). In 1995, on the night of their high school graduation, Chris attends Jamie's graduation party, and confesses his feelings to her by writing them in her yearbook; when he tries to return her yearbook to her, however, it is swiped by Jamie's ex-boyfriend Tim (Ty Olsson) and he reads it aloud at the party. Chris is then publicly humiliated when she doesn't reciprocate his feelings, instead giving him a kiss on the cheek and saying she loves him like a brother. After Jamie yells at their classmates for making fun of him, Chris storms away humiliated from the party on his bicycle, vowing to leave town and become more successful than all of them.
Ten years later, Chris is handsome and successful with a thriving career as a record producer in Los Angeles and a reputation as a ferocious womanizer. Just before Christmas, his boss (Stephen Root) orders him to take up-and-coming pop singer Samantha James (Anna Faris) to Paris so that she will sign with their company. Chris goes reluctantly, as he has a history with the self-obsessed James. On the duo's "business" trip to Paris, Samantha sets her private jet on fire by neglecting to remove the aluminum foil from her microwave dinner. This necessitates an emergency landing in New Jersey, not far from Chris's hometown. He takes her to his mother's house for the night, causing him to face the humiliating high school years he left behind and his unresolved feelings for Jamie.
Stepping out to the local bar, Chris runs into some old friends, including Jamie, who is working her way through graduate school as a bartender. Thinking that he can finally get his high school love out of his system, Chris plans to woo and seduce Jamie. However, a number of unexpected problems and the growing realization that his friendship with Jamie actually did mean something to him keep getting in the way. He bonds with Jamie on several occasions. But Dusty Lee Dinkleman, an even nerdier kid in school has now become a successful musician, and plans to have sex with Jamie and publicly humiliate her like she did to him when she told him she didn't like him. Jamie and Dusty bond and eventually he turns her against Chris when Samantha destroys Jamie's family's Christmas decorations thinking that Chris was sleeping with Jamie behind her back (she thinks that she and Chris are in a relationship). Angry and disappointed with Jamie and her family, Chris returns to LA only to realize that Jamie is the one for him. He leaves for his hometown again, goes to Jamie's house, and declares his love for her. And the film ends with some neighborhood kids watching Jamie and Chris kiss and a little boy gives one of the girls a cookie he made for her and she says "Thanks, you're a good friend'" suggesting that he may go through the same experience.
(Source: WikiPedia. Bangs_McCoy)
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