This article's plot summary may be too long or excessively detailed. Please help improve it by removing unnecessary details and making it more concise. (September 2015) (Learn how and when to remove this template message)In 1995, Chris Brander (Ryan Reynolds) is an obese high school student with a lisp, braces, and a "gentle giant" demeanor. He attends the graduation party of his best friend, Jamie Palamino (Amy Smart), whom he secretly has a huge romantic crush on. He plans to confess his feelings by writing them in Jamie's yearbook. When Chris tries to return Jamie's yearbook, it is taken by her despicable ex-boyfriend, Tim (Ty Olsson), who reads the declaration aloud to everyone and humiliates Chris. Jamie doesn't reciprocate his romantic feelings; after they share a brief kiss on the cheek, Tim and the class burst in and humiliate Chris again. Chris tearfully leaves the party, announcing that he would never return and vows to be more successful than everyone.Ten years later, Chris has lost weight, is handsome, and lives in Los Angeles; he is a womanizer who has dated supermodels, starlets, and socialites and works as a highly successful record producer. Prior to Christmas, Chris's employer, KC (Stephen Root), asks Chris to accompany an emerging self-obsessed pop singer named Samantha James (Anna Faris) 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's hometown.Chris takes Samantha to his mother's house to spend the night and re-engages with his teenage past, including his unresolved feelings for Jamie. Samantha meets Chris's mother and 18-year-old brother Mike (Christopher Marquette) who has an enormous crush on Samantha (ironic, because she has a crush on Chris). At the local bar, Chris encounters some old classmates, including his best friend Clark (Fred Ewanuick) and Clark's wife Darla (Amy Matysio); he also encounters Tim, who is now balding, fat, and a heavy drinker. Jamie also appears, working as a bartender to support herself through graduate school.Chris plans to impress and seduce Jamie. He gets Mike to keep Samantha busy during his date with Jamie, but the realization that Jamie's platonic friendship is important to him hampers Chris's plan. During a friendly ice skating "day date", Chris is taken away in an ambulance after injuring himself. At the scene, Jamie is reunited with Dusty Dinkleman (Chris Klein), a paramedic and former high school nerd who was also romantically in love with her.That night, in an attempt to rectify his situation, Chris again leaves Samantha in Mike's hands and takes Jamie to a movie showing of The Notebook. Jamie, however, brings Dusty along, and Chris's mother ends up joining them, ruining Chris's plan. Meanwhile, Samantha plays a gig at the heavy metal club that Chris sent her to, gets booed off the stage and assaults a member of the audience.The next night, Chris goes to Jamie's for a Christmas party, planning to reveal his feelings for her, but he finds Dusty already there winning the guests over with his charm and musician talents. Back at Chris's place, Samantha ambushes Mike and pushes him against the bathroom wall demanding to find out Chris's location; fully aware of his feelings, she passionately tongue kisses him until he tells her where Chris has gone. In a rage, she drives to Jamie's house and crashes through her fence, destroying her family's Christmas decorations. Chris returns home in embarrassment, and Jamie follows him; she tells him she is not mad and they end up spending the night together catching up and looking at photos, but due to Chris's continuing lack of assertion, the two end up falling asleep and no romance ensues.The next day, Jamie speaks with Darla about the night before and her fear that Chris's lack of affection means that he doesn't like her. Jamie admits that while the two are "just friends", she tried to "put herself out there" to Chris, to show Chris that she is interested in a relationship. Meanwhile, Chris goes to Clark's medical office to get advice, saying that "the timing wasn't right" and Jamie and Chris's history hinders his willingness to have sex with her. Outside the office, they happen to catch Dusty singing to a sexy nurse and then kissing her. Dusty reveals to Chris and Clark that he only plans to have sex with Jamie, as he wants to humiliate her in the same way that he felt she used to humiliate him when he was a nerd and she was the object of his crush.Chris tries to warn Jamie, but instead ends up attacking Dusty in front of her; Jamie refuses to listen when Chris tries to explain. Chris consequently gets drunk and goes to the bar where Jamie works, blaming her for keeping him in the "friend zone" and saying that she "peaked in high school" and will never amount to anything. Jamie punches Chris and he is tossed out of the bar.Upon returning to LA and having a frightening reunion with Samantha (who sneaks into Chris's house to "surprise him"), Chris realizes that Jamie is his one and only official and true love. He returns to New Jersey hoping to finally be with her. Chris declares his genuinely intense romantic love for Jamie at her house and the two share a kiss outside, in view of the neighborhood kids.
Output: Question: who plays Tim?, Answer: Ty Olsson