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
In 1995, New Jersey, obese high school senior Chris Brander (Ryan Reynolds) is secretly in love with his classmate and best friend Jamie Palamino (Amy Smart). Jamie and Chris have been friends for a really long time.Confessing his feelings by writing in her yearbook, he attends their graduation party. Chris' friends are rooting for him to get out of the "friend zone" with Jamie. Jamie leads Chris on in all sorts of way. She has many admirers like the freckled face Dusty Dinkleman, who has written a song for Jamie.As he returns Jamie's yearbook, it is swapped by her ex-boyfriend, Tim (Ty Olsson), who reads the declaration aloud to everyone, humiliating Chris. After kissing him on the cheek, Jamie admits she does not reciprocate his affections and thinks of him like a brother. Chris leaves the party in tears, announcing he will never return and vowing to be more successful than everyone else.
Ten years later, a womanizing Chris has lost weight and lives in Los Angeles as a successful record producer and vice president of the company. Chris was aspiring female musicians throwing themselves at him and he treats all of them like a one-night stand and is not interested in anything more than sex. He now advises his friends on how to avoid the "friend zone" with the girls.
Before Christmas, company CEO KC (Stephen Root) asks him to accompany emerging pop singer Samantha James (Anna Faris) to Paris so she signs with their label, and Chris reluctantly complies. KC insists on Chris as he went on a date with her. Chris says that Samantha is a crazy person. KC wants Samantha as she has just released a provocative poster, with her breasts covered in ice-cream, and it is the hottest selling poster in the USA. MTV just got her a new reality show. If she signs with their label, the label gets free promotion. KC says that he will fire Chris if he cannot deliver Samantha.
Samantha is extremely difficult to work with and has her own quirks and fancies.Samantha wants a relationship with him, but Chris has no interest after their only date previously led to his hospitalization. Samantha is all over the place, wants to lick Chris's skin off, acts like a cat, is completely horny and so on. She is a female rock star. She takes Chris' pants off for sex, and then makes him listen to a new song that she wrote.On the way to Paris, Samantha accidentally sets her private jet on fire (when she microwaves tuna in a tin foil), causing an emergency landing in New Jersey, near Chris' hometown.
Chris takes Samantha to his mother's Carol (Julie Hagerty) for the night and re-engages with his teenage past, including his unresolved feelings for Jamie. Chris' shrine for Jamie is still intact in his room.She meets his mother and 18-year-old brother Mike (Christopher Marquette), a fan of Samantha who is infatuated with her. At a bar, Chris encounters old classmates, including his other best friend Clark (Fred Ewanuick) and his wife Darla (Amy Matysio). Tim is now bald and a certified loser.
Chris also sees Jamie, working as a bartender to pay for graduate school for teaching. Jamie is still living with her parents. Chris asks Jamie out, but she invites him for lunch, immediately putting him into the friend zone. Chris asks Mike to keep Samantha busy during his date with Jamie, but realizing their platonic friendship is important to him hampers his plan for them to have sex.During a friendly ice skating "day date", Chris is taken away in an ambulance after injuring himself during a hockey game with Jamie and three kids (who dislike him). At the scene, Jamie is reunited with Dusty Dinkleman (Chris Klein), a paramedic and former high school classmate also in love with Jamie even now.
The next night, Chris goes to Jamie's Christmas party to express his feelings for her, but Dusty is already there, charming everyone on guitar. Back at Chris's, Samantha ambushes Mike, demanding he reveal Chris's location. He refuses until she kisses him. Enraged, she drives to Jamie's, crashing through her fence and destroying the Christmas decorations. Chris returns home in embarrassment, and Jamie follows. Jamie says she is not mad, and they spend the night catching up and reminiscing. However, due to Chris's continuing lack of assertion, they end up sleeping and nothing happens.
The next day, Jamie speaks with Darla about the night before, while Chris goes to Clark for advice. Jamie admits that while they are "just friends", she tried to show Chris she is interested in more. Clark tells Chris that "the timing wasn't right" and their history hinders him. Outside the office, Chris and Clark catch Dusty singing to a nurse and then kissing her. Dusty reveals his plans to have sex with Jamie and humiliate her in a way he felt she humiliated him in high school when he was attracted to her.
Chris tries to warn Jamie but instead attacks Dusty in front of her. She refuses to listen when he tries to explain. Consequently, he gets drunk and goes to Jamie's bar, finding her there with Dusty. When she gently declines Dusty's sexual advances, he storms out. Chris and Jamie get into another fight, where he blames her for keeping him in the "friend zone" and says she will never amount to anything. Furious, Jamie strikes Chris and he is tossed out.
Upon returning to Los Angeles and rejecting Samantha's continued advances when she sees him again, Chris realizes that Jamie is his one and only true love. He returns to New Jersey, declares his love to her and they kiss, while the three kids watch in disgust. One of the boys hands the girl a cookie, which she gives to the other. She calls the boy who gave her a cookie her friend, to which he replies with "the Bestest" before realizing he has been put in the friend zone.
