Make His Pockets Hurt

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Make His Pockets Hurt is a slang term used on the internet to describe a situation in which someone suffers financially or experiences a significant financial loss.”

Examples:

Just bought a new car and now my pockets are hurting!
My friend decided to invest all his savings in an unsuccessful startup, and it really made his pockets hurt.

Synonyms:
drainbank, emptywallet, emptypocket
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