(1) Unexciting, unadventurous, mainstream or dull. Generally used in describing a person with such attributes or who plays it safe. Historically, derived from a person whose goal in life is to have three "squares" a day (see definition (3) below), a roof over his head, a respectable job, a house, 2.5 kids, etc. Became a hip/popular expression of derision of the mainstream in the beat generation.
by Lewballs February 22, 2024

by Sepheryah December 15, 2017

Did you hear about the mathematician that got convicted of robbery? He went straight to a square based prison.
by TheFunnyGuy88 July 24, 2022
