"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."
"Damn, you can't win for losing."
by Kraas March 05, 2008
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
by dragonboy8586 October 16, 2019