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Just before his 1989 high school-championship basketball game, 17 years-old Mike O'Donnell's (Zac Efron) girlfriend Scarlett (Allison Miller) tells him that she is pregnant. He leaves the game and a possible college basketball scholarship to propose to her.
Two decades later, Mike's (Matthew Perry) life has stalled. Scarlett (Leslie Mann) has separated from him due to his regrets about abandoning college, forcing him to move in with his geeky and wealthy best friend since high school, Ned Gold; he quits his job; and his kids Maggie (Michelle Trachtenberg) and Alex (Sterling Knight) want nothing to do with him. While visiting Hayden High School to reminisce, an encounter with a mysterious janitor (Brian Doyle Murray) transforms Mike into his 17 year-old self.