Neal's been trying to get over a break up with his ex after walking in on her having sex with his best friend. Neal attempts to get over her by doing what anyone would do, tricking women on the internet. With the help of his buddies, Neal begins setting up fake dates with women who have placed Missed Connections ads. The plan is: Neal responds to a woman's Missed Connections ad saying that he is the guy she is trying to find (which he isn't), and sets up a date with the woman. He goes to the bar and watches as the woman waits for someone to show up, but doesn't. Just as she is about to leave, Neal approaches her and tells her that he wouldn't have stood her up. Neal's plan is going well until he meets Jane. Jane is getting over her last relationship by writing Missed Connections ads, setting up dates, and then watching as the guy waits for his "date." Needless to say, they are both pretty damaged, but they might just be what they each need to actually get over their past relationships.