Uptight lawyer Peter Sanderson wants to dive back into dating after his divorce and has a hard time meeting the right women. He tries online dating and lucks out when he starts chatting with a fellow lawyer. The two agree to meet in the flesh, but the woman he meets — an escaped African-American convict named Charlene — is not what he expected. Peter is freaked out, but Charlene tries to convince him to take her case and prove her innocence. Along the way, she wreaks havoc on his middle-class life as he gets a lesson in learning to lighten up.
Van Wilder has been attending college for far too many years and is scared to graduate, but Van’s father eventually realizes what is going on. When he stops paying his son's tuition fees, Van must come up with the money if he wants to stay in college, so he and his friends come up with a great fund-raising idea – throwing parties. However, when the college magazine finds out and reporter Gwen is sent to do a story on Van Wilder, things get a little complicated.
During the summer of 1999, a group of teenagers, through interconnected narratives, live through their last day of high school and prepare for the future. Holly, once the new girl in school, does whatever it takes to remain popular. Dawn, who is secretly a lesbian, battles drugs. Tori is the valedictorian of her class, but, on the eve of graduation, she decides to experiment with drugs for the first time.
