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Difference between Square up to someone and Square up with someone

square up to someoneshow courage in confronting a person:

  • In the street was a group of lads obviously waiting for. I had little option but to square up to them.

square up with someone

1. pay smb. the money one owes (leaving a restaurant, checking out of a hotel, etc.):

  • Can I leave you to square up with the waiter?

2. retaliate upon a person:

  • He wanted to “square up” with them, but had no definite plan of action, and was trusting to luck for something to turn up in his favor.