It's a month before the prom at Gilmore High and senior Ryan Woodman (SHANE WEST) doesn't have a date, but still maintains his longtime crush on Ashley Grant (JODI LYN O'KEEFE), the prettiest and most popular girl in school. The problem is, Ashley doesn't even know who Ryan is, particularly since he hangs around with Floyd (AARON PAUL), Cosmo (COLIN HANKS) and Dunleavy (MANU INTIRAYMI) who collectively epitomize the notion of "geekdom."
Ryan's best friend, however, is Maggie (MARLA SOKOLOFF), the girl next door who, despite possessing both beauty and brains, doesn't have a date to the prom either. A solution presents itself when Ashley's cousin, Chris (JAMES FRANCO), proposes a partnership of sorts with Ryan. It seems that despite Chris' popularity at Gilmore, he can't get Maggie interested in him. Thus, he tells Ryan that he'll help him get a date with Ashley if he helps him with Maggie.
With desperation winning out over reluctant better sense, Ryan agrees to the plan. As such, Ryan informs Chris of Maggie's favorite things and even feeds him poetic lines to impress her, while Chris tells Ryan that the best way to get Ashley's attention is to be a jerk to her. Although their dual plans begin to work and the young women begin to fall for the anxious young men, Ryan eventually discovers that Chris' intentions aren't honorable, that he can't live his life acting like someone he's not, and that he's actually interested in Maggie himself.