What is Can't Win For Losing?
1.
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."
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1.
Used as a term to show surprise, followed by confusion, followed by triumph.
Originally created as a Guild name on Elune US servers in ..
