To ask someone for their completely honest and unrestrained opinion. Comments made while squaring with someone are considered of utmost secrecy unless specified otherwise by the person talking.
Holding a copy of a new game in his hand, Jake said, "Square with me, Chris. What do you think of this game?"
by Voar June 9, 2007
A challenge; issued by a geezer to look him/her straight in the eyes. A way of showing how 'ard you are to others.
by Zero_Vector March 30, 2004