A person who has been "around the block" has experience, because they have been to different places and done different things. Example: "Don't think you can fool me so easily: I have been around the block." You know more, because you have seen and done more, once you have been around the block. Example: "You kids are too young to fall in love: Wait until you have been around the block a time or two." We sometimes question the type of experience a person has had when they have been around the block. Example: "I would stay away from that man if I were you. He has been around the block."