Ryan (FREDDIE PRINZE, JR.) and Jennifer (CLAIRE FORLANI) are clear opposites of one another, and always have been, but they have a definite knack for repeatedly running into each other. After briefly meeting on an airplane ride four years earlier, it's now high school and Ryan is a classic dweeb and control freak, needing to know and plan every aspect of his life. Jennifer, on the other hand, is a freewheeling spirit who hates plans and commitments.
The two don't really get to know each other, however, until Ryan attends the University of California, Berkeley, where Jennifer is already a sophomore. Due to their previously awkward and strained friendship, the two get on with their studies - he engineering and she Latin - but manage to keep bumping into each other, eventually becoming loose friends who commiserate about romance, dating and relationships.
Their respective roommates, Hunter (JASON BIGGS) and Amy (AMANDA DETMER), can see that the two of them are attracted to one another, and can't believe they don't see it or won't allow themselves to admit it. Nonetheless, the two continue through college, with Jennifer continuing to date various guys while Ryan doesn't, seemingly using her as his surrogate and thus safe "girl-friend."
Yet, the two become closer and despite Ryan eventually dating another student, Megan (HEATHER DONAHUE), they end up in bed together. From that point on, as they teeter between friendship and love, the two must figure out what's right and wrong for themselves as individuals, friends and possible lovers.