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Just Friends
In 1995, obese high school senior Chris Brander is secretly in love with his classmate and best friend Jamie Palamino. Confessing his feelings by writing in her yearbook, he attends their graduation party. As he returns Jamie's yearbook, it is swapped by her ex-boyfriend, Tim, who reads the declaration aloud to everyone, humiliating Chris. After kissing him on the cheek, Jamie admits she does not reciprocate his affections. He leaves the party in tears, announcing he will never return, and vows 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. Before Christmas, company CEO KC asks him to accompany emerging pop singer Samantha James to Paris so she signs with their label, and Chris reluctantly complies. While she wants a relationship with him, he has no interest after their only date previously led to his hospitalization. On the way to Paris, Samantha accidentally sets her private jet on fire, causing an emergency landing in New Jersey, near Chris' hometown.
Chris takes Samantha to his mother's for the night and re-engages with his teenage past, including his unresolved feelings for Jamie. She meets his mother and 18-year-old brother Mike, a fan of Samantha. At a bar, he also sees Jamie, working as a bartender to pay for graduate school for teaching. 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. At the scene, Jamie is reunited with Dusty Dinkleman, a paramedic and former high school classmate also in love with her.
Realizing Dusty only wants revenge sex with 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 again, Chris realizes that Jamie is his true love. He returns to New Jersey, apologizes to her, and declares his love before they kiss.