Though Kevin is young, handsome and working his way up in the advertising industry, he doesn't have too much confidence when it comes to meeting women. After meeting Abbey, his dream girl, on the L train, he fails to get her phone number. He and his pals resort to postering the Windy City with flyers displaying his phone number in the hopes of finding his subway sweetheart. As a result of his massive campaign, Kevin becomes Chicago's poster boy for lost love and the object of every woman's affections. But the fates that brought Kevin and Abbey together on the "L" seem determined to reunite them, revealing that love will give you a second chance if you are willing to put yourself "on the line".