Hogan "Hoagie" Malloy, Bob Callahan, Randy "Chilli" Cilliano, Kevin Sable and Jerry Pierce have been playing tag since they were nine years old, starting in 1983, during the month of May. Since then, the group’s main rule of the game is that the last one tagged is “it,” until next season. With Hoagie having been the last one tagged in the previous year, he first recruits Bob, the CEO of an insurance company, and then Chilli and Kevin for one last attempt to tag Jerry, who has seemingly never been tagged because of his strong athleticism and intelligence. Hoagie tells them that Jerry plans to retire after this year's game because of his upcoming marriage. Rebecca Crosby, a ''Wall Street Journal'' reporter doing a piece on Bob, joins them and decides to write an article on the friends. They are also accompanied by Hoagie's wife Anna.