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A way of saying you're so dumb and broke you're basically a trash can full of old pizza and regret.
My mom said I was a day late and a dollar short because I forgot my wallet and my brain at the same time.
My friend tried to ask me out but I was already with someone else. I told him, 'You're a day late and a dollar short, buddy.'
My dad said I was a day late and a dollar short because I showed up to work 2 hours late with no money and a face full of sadness.