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There are 2 eighteen-letter words beginning with PLAYWI

play␣with␣edged␣tools play␣with␣house␣money

3 definitions found

play␣with␣edged␣tools — v. Alternative form of play with edge-tools.
play␣with␣house␣money — v. To be a situation where little or no personal risk can be incurred. — v. To act as though little or no risk can be incurred.

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