Andrea "Andie" Williams and Dexter Robinson have known each other since they were in diapers. While their parents are the best of friends, the two are barely even acquaintances. While Dexter is the most popular guy at Williamson High School and only cares about which girl he will sleep with next, Andrea is focused on getting into her dream college, Yale. When they are placed together for an unlikely project, the two have to come together not only to pass their class, but also graduate. With a series of events surrounding them, they both realize that their first experience at love could be with the person who was right in front of them all along.