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win the losing lottery

To win at something no one should be proud at winning.
I won, I was the dumbest that was there. Congratulations, you (won)/ win the losing lottery.
by foodboy96 March 30, 2024
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Can’t win for losing

When you voluntarily lose (to make someone feel better, to end an argument), and then the situation gets even worse. So, what you thought you would gain by losing on purpose is lost anyway.

It’s a colloquial equivalent to paving the road to hell with good intentions.

(A lot of people writing their definitions for this are trying to make logic out of the phrasing but weren’t around when this phrase was more popular, leading to incorrect definitions.)
I let my spouse win the argument to calm down the situation, and now I’m getting criticized for not sticking up for myself. I can’t win for losing!
by Jemie Weino October 8, 2022
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losing

what’s losing?

i don’t know, never have never will
by themilfman69 May 25, 2021
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lose hearing in my left eye

funny way to describe the fact you’re missing something or someone for an extended period of time.
“omg i miss you sm, im starting to lose hearing in my left eye
by pickle tickle August 7, 2024
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lose an oyster

Don’t lose an oyster Becky! Chad doesn’t deserve you.
by Breadluvr July 2, 2019
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Lose my shit

I’m gonna lose my shit on your dumb ass if you don’t stop your shit.
by The real him March 13, 2023
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