| Director | Eric Bross |
|---|---|
| Genre | romantic comedy |
| Runtime | 85 min |
| Country | United States |
| Budget | $16 million |
| Box office | $4.5 million |
Romantically awkward and shy Kevin Gibbons works in Chicago for an advertising firm. He makes a pitch for Reebok that is rejected, but his colleague Jackie later proposes Kevin's idea, claiming it as her own, and it is approved. While riding the "L" Train home, Kevin meets Abbey, with whom he has an immediate connection and finds they have mutual interests in the Chicago Cubs and Al Green; however, Kevin lets Abbey leave without even learning her name. Lamenting having let her get away, Kevin tries to find Abbey by making posters asking the 'L-Train Girl' to contact him and placing them all over town. He is initially optimistic when he receives the first few calls, but none of them are from Abbey.
Local reporter Brady Frances, an old classmate of Kevin's who still holds a grudge against him because of a girl who rejected him for Kevin, is tasked by the Chicago Daily Post with interviewing Kevin about his search. When Frances's article is published, Kevin is flooded with calls and his roommates — aspiring musician Rod, slacker Eric, and art aficionado Randy — suggest they date the callers, framing it as a way to help filter out all the time wasters. Kevin rejects this idea, but a miscommunication leads Eric to believe that Kevin has approved it. Brady publishes a follow-up article, portraying Kevin as a loser and failure, which results in even more calls from women. Meanwhile, Abbey is having problems with her boyfriend, who lives in Chicago and she was visiting when she met Kevin.
Frances has his girlfriend Julie, who is on Kevin's side, call Kevin posing as the L-Train Girl; she subsequently goes on a date with Rod and informs Frances that Kevin's friends are answering the calls and dating the respondents. Brady reports that Kevin's search is a scam, as a result Reebok declines to work with Kevin and he is taken off the project. Abbey sees Kevin's poster and contacts him but the call is answered by Eric, who arranges a date with her, where he realizes she is the one Kevin is looking for; before he can explain, Abbey leaves the restaurant in disgust. Kevin subsequently sees Abbey waiting for a train and runs after her, but prompted by her meeting with Eric and Frances's story about Kevin, she ignores him. Kevin later becomes angry at Eric after learning he met with Abbey and didn't tell him.
While contemplating giving up, Kevin visits Nathan, his best friend at the firm, in rehab after he suffers a heart attack. Nathan reminisces about meeting his wife at a Chicago Cubs game, where he caught a home run from Cubs legend Ernie Banks, and encourages Kevin to keep looking for Abbey. Jackie apologizes to Kevin for plagiarizing his work and puts him in charge of the billboard campaign. Kevin uses the billboards to publicly ask Abbey to meet him at the train station at 7pm on Friday. Eric tries to make amends with Kevin by placing posters all over town imploring Abbey to attend the meeting, and gives an impassioned speech about love on a train, which Abbey overhears.
Inspired by Kevin wearing his heart on his sleeve, Rod composes a love song; Kevin secretly sends a demo tape of it to rock star Mick Silver, who turns up to see Rod perform at a bar and offers him a record contract. Randy meets a woman who enjoys art as he does, Julie leaves Frances for Rod, and Frances is given an advice column in the Chicago Times. Finally, crowds and TV crews gather at the train station in anticipation as Kevin waits for Abbey; though 7pm passes, Abbey appears and all of Chicago celebrates as she and Kevin are reunited.