Ben Wrightman, a 7-year-old boy, is going to a Boston Red Sox game with his Uncle Carl. His uncle, who had no children of his own, treated Ben like a son. A narration explains that on that day, Ben became a Red Sox Nation. Just about everything he owns bears the Red Sox name, emblem, or image of a Red Sox player (with the exception of his toilet paper, which bears the New York Yankees insignia). Ben inherited his uncle's season tickets when Carl died from cancer. The story picks up 23 years later with Ben (Jimmy Fallon) as a school teacher who is immature for his age. He meets Lindsey Meeks (Drew Barrymore), a professionally successful workaholic executive. When Ben first asks her out, Lindsey rejects him, but she later changes her mind and agrees to go out with him.