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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Lose-Lose Win-Win

1. Think of something you know you need to do, but that you don't want to do.
2. Stop waiting and go do it.
3. Don't listen to me.
4. Don't let me tell you what to do.
5. Do what you want.

And that's an example of a lose-lose win-win.

by Ferington January 27, 2021

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Lose my pills

To be angry or upset

If my kid gets out of bed one more time, I’m going to lose my pills.

by Fofoxsake February 1, 2021

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Losing your man privilege

When someone goes ching-chong in your ding-dong

losing your man privilege is funny until it happens to you

by retardJim69420 February 11, 2021

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Losing your squareness

Losing your squareness means to kiss a boy or girl with tongue for the first time.

Example: I lost my squareness to Betty the other day. It was moist and squishy but I liked it.

Example: Did you enjoy losing your squareness to Betty?

Definition: To kiss someone with tongue for the first time.

by Lord_Bibblinngton April 1, 2021

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