"It's all about timing", is Joel's motto as he uses his second chance in life to ask Holly Kent to the Valentine's Day dance. Well, that and a red rubber ball, as we later discover as he seizes his moment during a game of Dodgeball, when he steals the woman of his dreams from possessive Gary Ross. Joel also tells his best friend that the girl who said at her High School 10-year-reunion that she always fancied Pat, was a girl called Stacey and so they pair off also. Isabelle finds her man in Todd York with whom she was last seen in a bitter argument at their Model U.N. Conference. When it comes to the crunch during the main dance, Joel is torn between staying linked with Holly, and persuading his parents, who came along as chaperones, that they should be dancing together rather than his father throwing his marriage into the toilet by insisting that Saturday night is always "Poker Night". Which way will he choose?

Joel is thrust back 20 years into the past, where his first order of business is to survive algebra class and keep from being humiliated in the student council election.

Joel picks a fight with a high school bully. This time around, he decides to stand up for himself.

Joel is faced with re-living one of the most embarrassing moments of his life: when he made his baseball team lose the game after missing 3 balls. He tries his best to avoid playing at the game, but his efforts are useless. He will have to see his dad yell at him, his mother run away with shame, his sister call him a dork, Holly Kent laugh at him and worse: this time his grandpa, Isabelle (who's having a bad hair week thanks to a bad perm) and TV are there. Joel misses the balls, but instead of running home like before he stays and faces everybody. Turns out his dad was yelling at someone else, his mother just went to pick up sodas from the car, Holly Kent was laughing at some dogs and his sister was really calling him a dork. Facing his failure isn't so bad after all, especially when you discover you were the one who gave Greg Maddux confidence to carry on with his future brilliant baseball career. Pat, on the other hand, isn't so lucky and has gets his wrist broken like before.

Pat makes Joel steal his dad's precious Cadillac and go to the Def Leopard concert so they wouldn't be stuck home "with only three networks". At the concert, Joel uses his smooth talk to buy tickets from a scalper for him, Pat, Isabelle and Holly Kent, who he met at the parking lot waiting outside for her date to come out of the concert. Just as they are about to get in, Joel changes his mind and rescues his sister from the most humiliating night of her life. Unfortunately, he is caught red handed and his parents decide to act tougher on him – thanks to melancholic, depressive poem he wrote in English class entitled "Smells Like Teen Spirit" – and Cheryl doesn't remember a thing the morning after.

It's Halloween, and Joel has a chance to rewrite what was his first kiss, which he accidentally had with Bonnie, an annoying girl who would end up dating him against his will for 6 months after that. How surprised is Joel when he sees Bonnie at the party she was not supposed to be at, thanks to an invitation made by Pat. In a desperate moment, Joel kisses Isabelle, and convinces her to pretend she's his girlfriend for the night. When he sees Holly Kent break up with her boyfriend of the week, Joel quickly dumps Isabelle, who gets hurt. Joel finally has the opportunity of a lifetime when Holly asks for a kiss, but chooses not to do that when he sees she'd only be doing that to cause jealousy on her boyfriend. They go home and start cleaning the t.p.'s that are all over the Larsen home, since they are "the raisins house" (while Bill and Karen get things heated up in the backyard with Tarzan and Jane costumes), leaving Pat making out with Bonnie and Cheryl trading one loser for a guy who would eventually become a famous cardiologist, if it wasn't for her influence.