zack and douglas siler (freddie prinze jr. and matthew lillard) are two of the most popular people at their southern california highschool. zack's girlfriend, beautiful taylor vaughan (jodi lyn o'keefe), who is also very popular, breaks up with him so she can instead be with brock hudson (owen wilson), who is famous after being on a reality television show. zack is sad but tells himself, he could make any girl in the school popular by making her his girlfriend. zack and douglas's friend, dean sampson, jr. (paul walker), does not believe him and makes zack bet that he can turn any random girl into the prom queen within six weeks, and douglas's childhood friend donald hamilton (richard hammond) believed that zack could turn any random girl into the prom queen within six weeks. but dean chooses laney boggs (rachael leigh cook), an unpopular art student, who prefers to spend time by herself.