been around the block 

A person who has learned from relevant experiences in the world
- Street smarts
- wisdom
- real-world experience
- seen a thing or two

"If your not sure how to run this business, ask Old Man Dave. He's been around the block a few times"
"Could tell Mayor Hudson to fix the schools?" "No. Ask Shelly she's been around the block with her before"

been around the block by mazeradaville October 24, 2017

been around the block 

a person who has had sexual intercourse numerous times before

Jill sure has been around the block

been around the block by Yows May 13, 2004

been around the block 

A boy or girl, usually a girl, who has had sex with seemingly every person on the block

Guy 1: Yo i heard you was getting pussy cuz... any truth to that?
Guy 2: Yeah word up cuz
Guy 1: Yo who u gettin it from?
Guy 2: Ommmm... Suzy...
Guy 1: DAMN CUZ!! aint that bitch who was caught sucking the whole football teams dicks after the game friday night??
Guy 2: Ommm... i dont know...
Guy 1: Man that bitch been around the block

been around the block by Killa Cam February 17, 2005