can't win for losing 

A phrase meaning that things would be going great for you if they weren't going so badly.

"Well, my girlfriend dumped me, my dog died, I got fired from my job, I went to grab some fast food to make myself feel better and on the drive back I got a flat tire, and when I finally get home I realize they screwed up my order."
"Damn, you can't win for losing."

can't win for losing by Kraas March 5, 2008

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!

Can’t win for losing by Jemie Weino October 8, 2022

You can't win for losing 

When you win something but , winning means you lose either psychologically emotionally physically financially, anyway that negatively impacts you.

You do the dishes cuz your parents told you to and ,then when you're finished they yell at you for doing it wrong even though they didn't tell you how to do it in the first place ! Man you can't win for losing

You can't win for losing by dragonboy8586 October 15, 2019