Ryan Reynolds (Green Lantern)
Amy Smart (Roas Trip)
Anna Faris (Mom)
Chris Klein (Election)
Chris Marquette (Fanboys)
Fred Ewanuick (The Core)
Julie Hagerty (Airplane)
Barry Flatman (Odyssey 5)
Robin Dunne (Sanctuary)
Ashley Scott (Birds of Prey)
Ty Olsson (Battlestar Galactica)
In 1995, Chris Brander (Ryan Reynolds) is an obese, curly-haired 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). Chris is publicly humiliated when Tim reads his (Chris) confession aloud to the party but is further demoralized when Jamie doesn’t reciprocate his intense and close romantic feelings and affections. After they share a kiss, Tim and the class burst out and humiliate Chris again. Embarrassed, Chris leaves on his bicycle tearfully and vows to leave town and never return in order to achieve greater success than his classmates.
Ten years later, Chris has lost weight, is handsome, lives in Los Angeles, womanizer who has dated supermodels, starlets and socialites and works as a highly successful artists & repertoire rep (record producer) for a record label. Prior to Christmas, Chris’ employer, KC (Stephen Root), asks Chris to accompany an emerging, self-obsessed pop singer named Samantha James (Anna Faris) to Paris to ensure Samantha signs with him, 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 for a place 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, ironically, has a bigger crush on Samantha than she has on Chris. At the local bar, Chris encounters some old classmates, including his best friends who is Clark and his wife Darla who are married and have a kid and a successful dental practice, including 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 which Mike was only too thrilled about. Unfortunately Samantha ended up with a head concussion. Meanwhile a number of unexpected problems, including a growing realization that Jamie’s platonic friendship is important to him, hamper Chris’ plan. Chris bonds with Jamie on several occasions and during a friendly ice skating “day date”, Chris is taken away in an ambulance after being injured in a game of hockey. Jamie is reunited with Dusty Dinkleman (Chris Klein), a paramedic and former high school nerd who was also romantically in love with her. When Chris gets home he finds Samantha attempting to seduce Mike, who was in the process of giving her a backrub, and ends up fighting with them.
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, which he could not bring himself to enjoy. Chris’ mother and Dusty join them and Dusty’s sensitivity due to the movie causes Jaime to bond with him instead, much to Chris’ annoyance. Meanwhile, Samantha tries playing a gig at a club, gets booed off the stage and assaults a member of the audience.
The next night, Chris went to Jaime’s for a Christmas party, planning to reveal his feelings for her. But Dusty was already there and winning the guests over with his charm and musician talents, causing Chris to give up. Back at Chris’place, Samantha ambushes Mike and pushes him against the bathroom wall demanding to find out Chris’ location. Following initial resistance, Samantha, fully aware of Mike’s strong feelings towards her, passionately tongue kisses him, resulting in Mike’s immediate disclosure (thinking that Chris and Jamie have made love already, Mike uses the term “lover”). Samantha consequently becomes jealous towards Jamie, believing that the old classmates are in a relationship, and in an angry rage, Samantha destroys Jamie’s family’s Christmas decorations. Embarrassed by Samantha’s actions, Chris returns home but is visited by Jamie there. Jamie reveals that she is not mad at Chris and plans to spend the night with him; but, due to Chris’ continuing lack of assertion, the two end up falling asleep and no romance ensues.
The day after Samantha’s vandalism, Jamie speaks with Darla (Amy Matysio), who is now married to Clark (Fred Ewanuick), about the night before and her fear that Chris’ lack of affection might mean that he doesn’t like her. Jamie admits that whilst 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 attends Clark’s workplace, a dental surgery, to talk to Clark, revealing to him that “the timing wasn’t right” and that their shared history hinders his willingness to have sex with her. Chris explains that he feels like he is in high school again. Later, Chris and Clark catch Dusty singing to a sexy nurse and then kissing her. Dusty then 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. Chris tries to warn Jamie about Dusty during a children’s Christmas pageant, but instead ends up attacking Dusty and ruining the play. Jamie refuses to listen when Chris tries to tell her about the nurse, leaving Chris angry and disappointed with both Jamie and her family. Chris consequently gets drunk and enters the bar where Jamie works, proceeding to blame her for keeping him in the “friend zone”; he also exclaims that Jamie will never amount to anything romantic or meaningful. Jamie punches Chris and he is tossed out of the bar at her request. Upon returning to LA, and proceeding a rather frightening reunion with Samantha (who snuck into Chris’s house to “surprise him”), Chris realizes that Jamie is his one and only official and true love interest and 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 romantic kiss outside in view of the neighborhood kids.
Brilliant! Really good movie with a fun storyline and terrific actors. Ryan and Anna really make this movie. Anna is hilarious!!