Popular high school senior Mike O’Donnell (Zac Efron) seemingly has it all. He is a star athlete headed straight for a college scholarship when he decides to give it up to settle down with his high school girlfriend Scarlet.

Twenty years later, an adult Mike (played by Matthew Perry) finds his life is not exactly what he expected. He is separated from his wife, Scarlett (Leslie Mann) and living with his best friend Ned Freedman (Thomas Lennon), his career at a pharmaceutical company is at a stand still, and his relationships with his teenage children are nonexistent. After getting passed up for yet another promotion at work, he returns to his high school to reminisce over his basketball awards and the life he could have had. While he is reliving his past, he is approached by a janitor and shares with him how things were so much better when he was 17.