The origin of the idiom been around the block is uncertain. We will examine the meaning of the idiom been around the block, where it may have come from, and some examples of its use in sentences.
If someone is described as having been around the block, it means he is experienced, that he has been in a similar situation before, that he has worked on a similar task before, that he has skills acquired in previous similar circumstances. Someone who has been around the block knows what he’s doing. The idiom originated in the 1960s, probably in America, where neighborhoods are organized in blocks, which are squares or rectangles of land with evenly spaced houses. Be careful when you use the term been around the block. In some circumstances, the phrase means the person in question is sexually experienced. This meaning is particularly common in British English.
Owner Josh Beeby has been around the block a few times with his other two über-popular establishments downtown, Trappe Door and Barley’s Taproom. (The Greenville News)
“These guys are just top quality people and players, and then you look and see all the experienced guys who have been around the block.” (The Irish Times)
Most of the those homeowners who’ve been around the block a few times, want the city to upgrade the sewage lines and the utilities to put their lines underground/and or upgrade those that are, before they put in sidewalks. (The Californian)
But, the original has been around the block a time or two and can deal with basically whatever you throw at him. (The Maryville Daily Times)