Kevin (Lance Bass) is performing with his band at a high school graduation party. When he sees an attractive girl, his bandmates try to get him to sing to her and ask her out. He becomes nervous, and envisions himself nude in front of everyone, and faints. Seven years later, Kevin is working in advertising. He makes a pitch for Reebok that is rejected, though the pitch is later used in the meeting by his "partner" Jackie (Tamala Jones), who presents it as hers. As he takes the train home from work, Kevin meets Abbey (Emmanuelle Chriqui), with whom he finds he has much in common, such as their mutual interest in the Chicago Cubs and Al Green.
Kevin tries to find Abbey by making posters imploring Abbey to contact him, and placing them all over town. He goes out with a few random women who respond, none of whom are Abbey. The local newspaper finds out about his search and sets up an interview. The reporter, Brady Frances (Dan Montgomery, Jr.), is an old classmate who harbors ill will toward Kevin, on account of a girl in high school who rejected Brady for Kevin. When Brady's article is published, Kevin gets hundreds of calls, which leads to his dateless roommates — aspiring musician Rod (Joey Fatone); slacker Eric (GQ); and art aficionado Randy (James Bulliard) — suggesting they date all the callers to help. Kevin rejects this idea, but a miscommunication leads Eric to believe that Kevin has approved it. A follow up article is published in which Brady portrays Kevin as a failure, which garners even more calls from women. Brady is further irritated when his girlfriend Julie (Amanda Foreman), who is bothered by his grudge against Kevin, takes Kevin's side.
Meanwhile, Abbey is having problems with her boyfriend of three years, whom she was visiting when she met Kevin. Her boyfriend buys tickets to an Al Green concert, but then cancels at the last minute. Kevin is also at the concert, but they never see each other, despite several close calls. As Kevin's roommates date the women who responded to the articles in order to find Abbey, they encounter Julie. When she tells Brady that Kevin's friends are answering the calls and dating the respondents, Brady reports this as a scam in a follow-up article. As a result, Reebok declines to work with Kevin, and he is taken off the project. When Kevin subsequently sees Abbey waiting for a train, he tries to get her attention but she only sees him after she boards the train, and the doors close before he can get to her. Kevin also learns that Abbey responded to his public search for her, and when he learns that Eric went out on a date with her, he punches Eric.
After Kevin's best friend at the agency, Nathan (Jerry Stiller), suffers a heart attack, Kevin visits him at a rehab facility, where Nathan tells him the story of both meeting his wife at a Chicago Cubs game, and catching a home run from Cubs legend Ernie Banks the same day, and how the two events are tied together. He gives Kevin the baseball and tells him to try to find Abbey again.
Jackie apologizes to Kevin, and places him in charges of the campaign's billboards. He uses the billboards to publicly ask Abbey to meet him at the train station at a specific day and time, which garners the interest of the media, who wait with him at the scheduled time. Kevin and Abbey are reunited at the station, much to the delight of the crowd at the station, to the television viewers at home, and to his roommates watching this unfold in a bar. In addition, Randy meets a women who enjoys art as he does, Julie dumps Brady for Rod, who is offered a recording contract by a record label after listening to a demo tape of his that Kevin sent them, and Brady is given an advice column in the Living section of the Chicago Times.Lance Bass as KevinEmmanuelle Chriqui as AbbeyJoey Fatone as RodGQ (actor) as EricJames Bulliard as RandyJerry Stiller as NathanRichie Sambora as Mick SilverDave Foley as HigginsTamala Jones as JackieAmanda Foreman as JulieChyna as Rod's dateJustin Timberlake (uncredited) as Make-up artistChris Kirkpatrick (uncredited) as Angelo the hairstylistCameos as themselvesAl GreenAnanda LewisSammy SosaDamon BufordEric Young
According to a DVD release, the film was shot in Toronto, Ontario, Canada and Chicago, Illinois.
The original screenplay for the film would have received an R rating, but was rewritten to a PG so that it could be marketed to NSYNC fans.
The short film on which the film was based starred Troy Garity, Charlie O'Connell, and Eric Michael Cole.
During the credits of the film, the film features a comedic clip of Lance Bass and Joey Fatone who played two of the main characters being made up by fellow NSYNC members Justin Timberlake and Chris Kirkpatrick. Timberlake and Kirkpatrick played wardrobe managers yet NSYNC member JC Chasez failed to appear.
The film was produced on a US$16 million budget. Miramax marketed the film heavily towards *NSYNC's teen fans, and the film's soundtrack featured songs by teen pop sensations Mandy Moore and BB Mak, along with previously unreleased tracks by *NSYNC and Britney Spears. However, the film was a box-office flop, and grossed only $4.3 million domestically.
The film was heavily criticized, especially by star critic Roger Ebert, who said the film was "...an agonizingly creaky movie that laboriously plods through a plot so contrived that the only thing real about it is its length."
On Rotten Tomatoes, the film holds a 19% 'rotten' rating with the consensus stating "An inept attempt at a romantic comedy aimed at 'NSYNC fans."