To adopt a confrontational physical stance, ready to fight
"The younger boy squared up to the bully, refusing to back down despite being smaller."
To adopt a fighting stance, to settle a bill or debt, or to confront a challenge bravely
To get ready to fight someone, or to pay money you owe
3 meanings, ordered from most common to least. Color-coded by CEFR level.
To adopt a confrontational physical stance, ready to fight
"The younger boy squared up to the bully, refusing to back down despite being smaller."
To pay money that you owe someone; to settle a bill or debt
"Let me square up with you for last night's dinner — how much do I owe?"
To confront a problem, challenge, or difficult situation with courage
"Eventually she had to square up to the reality that the business was failing."
To square your shoulders and stand upright, ready to face opposition — a posture associated with readiness and honesty
To get ready to fight someone, or to pay money you owe
Has two main senses that are quite different: the financial sense ('let me square up with you') and the confrontational sense ('he squared up to the bully'). The financial sense is very common in casual British and American speech. The confrontational sense has a slightly old-fashioned or literary flavour.
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