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work both sides of the street

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Engage in doubledealing, be duplicitous, as in The real estate agent was known for working both sides of the street, advising first the buyer and then the seller. This metaphoric term transfers opposite sides of a street to opposite sides of a negotiation.

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SHALL WE PLAY A "SHALL" VS. "SHOULD" CHALLENGE?
Should you take this quiz on “shall” versus “should”? It should prove to be a quick challenge!
Question 1 of 6
Which form is used to state an obligation or duty someone has?

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The American Heritage® Idioms Dictionary Copyright © 2002, 2001, 1995 by Houghton Mifflin Harcourt Publishing Company. Published by Houghton Mifflin Harcourt Publishing Company.

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