The year is 2002. Joel Larsen is thirty-four years old, but has never really done anything special with his life. His parents are divorced, and his sister is a drug addict. But when Cheryl, his sister, puts him through a freakish accident, he is sent back to 1981, and suddenly he gets the chance most people dream of: to be a teen all over again. He first freaks out when he realizes he has to go through the 80s one more time, where everybody he knows is young again, while everything he used to know is gone and replaced by old-fashioned things. But slowly he accepts his...
When Joel irritates his crush Holly Kent's boyfriend Judd Chulak, he is challenged for a fight after school, which he agrees to go through with. This upsets Isabelle, since it collides with the premiere of "Empire Strikes Back", something they both have been looking forward to for months, but also because she is worried about him getting hurt. Joel does not know what to choose. He wants to go see the movie with Pat and Isabelle, especially since he is terrified by Chulak. But he is also afraid of letting down Bill, who always has believed his son is a coward.
Joel is tired of his parents always fighting about money, so he decides to take a job. He eventually chooses the one he has been stuck in for years in his alternative world - paper salesman. He gets the job, and does a wonderful job with it. But he discovers that it's got its price; he gets less time to spend with his family and friends, and is constantly tired. And as if this was not enough - Mr. Rudd overhears one of his phone conversations and thinks Joel is in the drug business. Joel's new job also annoys Pat, who wants to go to a Blues Brothers concert with him.
A new teacher by the name Ruben enters the school. But this is not what worries Joel the most - in the future, Ruben is his stepfather. So to avoid that his mother ever meets Ruben, he tries to encourage his parents to do something special on their anniversary. But his plan backfires, Ruben meets Karen six years before they are supposed to, and they immediately connect. Joel, who don't like Ruben very much, panics and tries to do everything that comes to mind to break them up. He even engages Cheryl to plot with him.
Joel and Pat are both trying to cheat their fates. Joel is to play in the state baseball championship, but remembers that he choked in the last throw and blew the team's victory, having everybody (including the ones he cares about) become disappointed in and laughing at him. Joel also tells Pat that on the same day he loses the championship, Pat breaks his wrist. Thereafter he tries everything to prevent that. Meanwhile, Isabelle is having a bad hair day.
Joel, Pat and Isabelle want to go to a concert, but Cheryl won't take them. They decide to drive there on their own. When they get there, both Joel and Isabelle experience new things. Meanwhile, Bill and Karen finds out that Joel fails almost every class and suspects him of taking drugs.
Joel is trying to rewrite the start of his dating history by going to a party with Holly Kent, with the goal to get the first kiss from her instead of a boring girl named Bonnie. He winds up kissing Isabelle in desperation, and becomes her fake boyfriend so Bonnie leaves him alone and to make Holly notice him. Meanwhile, Pat actually wants to get his first kiss from Bonnie, and Bill and Karen celebrates Halloween in their own way.
Joel discovers that he wrote a brilliant song last time he was a teenager, but he does not remember how to play it. Therefore he plays Green Day's "Good Riddance (Time of Your Life)" in the school's talent contest, which everyone loves. He is contacted by an agent for the television talent show "Star Search", who encourages him to play the song at the audition. So does his friends Pat and Isabelle (who signs up as manager and image consultant respectively), and even his parents eventually think it's a good idea. But Joel sits on information no one else has - the song ...
Isabelle gets her first date, but when Joel remembers that her date cheated on her, he and Pat must find a way to stop it from happening all over again. But when trying to help her, she thinks they are just jealous. Meanwhile, the Larsens prepare for the annual block party, but Bill threatens to destroy it all with his behavior, just like he did the last time Joel was a teenager.
Joel is frustrated of all the rules he has to follow at home and decides to stand up for himself against Bill. He envies Pat and Isabelle because he thinks they have perfect families, and wants a life more like that. That eventually leads to him getting kicked out of the house and he has to live with Pat and his carefree mother, which he loves. At home, Cheryl is, as a result of being the only child in the house, driven crazy by Bill and Karen.
Joel turns fifteen for the second time - but he would much rather celebrate his thirty-fifth birthday with a more grown-up birthday. Inspired by the future movie "Ferris Bueller's Day Off", he skips school along with a willing Pat and an unwilling Isabelle. But the sudden grown-up wish eventually drives Pat and Isabelle nuts.
When he is failing biology, Karen and Bill decide that Joel needs a tutor. He is not all that fired up about the idea, but has no choice. Although, he changes opinion when he sees his new tutor, the ten years older Abby. They immediately connect and he falls for her, but doesn't like that she dates a version of his future self. Meanwhile, Pat misreads something Joel tells him and starts flirting Isabelle, which annoys her terribly.
In the Valentine's dance last time Joel lived in the 80s, Joel, Pat and Isabelle went together, but now Joel wants to break the cycle and ask out Holly Kent, while Pat has his eyes on a girl who has a crush on him. Despite all his experience on the dating field in the future, Joel just can't find the courage to ask Holly. But when both Pat and Isabelle find dates to the dance, Joel decides that he must pull himself together. Meanwhile, Bill and Karen try to bring back the glory days at the dance.
Joel edges Bill to support Karen's business ideas, and Karen is really excited to present her ideas to the world. But then he hears the idea for her first pitch - chili mixed with spaghetti, which she calls Chilghetti. Joel completely shoots it down due to his future knowledge, to Karen's major disappointment. Meanwhile, Isabelle is planning on auditioning for the school's take on "Gone with the Wind", but Joel remembers that she completely screwed up the first time around and got teased for months, which was the worst time of her life. Joel and Pat must prevent it ...