(one) can't win(redirected from you couldn't win)
(one) can't win
1. One is unable to find or create any success; one has been constantly and/or thoroughly defeated, bested, belittled, etc., in recent times. So Mary divorced John after their company went under, and then his mother died a week later? Man, that guy can't win lately. That's the third manuscript to be rejected by the publishers. I guess I just can't win.
2. One cannot please someone or everyone. The kids aren't happy if they don't have the same fancy gadgets as their friends, and my wife's not happy if I buy the things for them—I can't win! First he criticizes me for spending too much time at home, then he criticizes me for being away too often with my friends. I just can't win with him.
you can't win
Also, you just can't win. Whatever one does is wrong or not enough, as in Every time I block one of the woodchuck's holes, I find another; you just can't win. [First half of 1900s] For a synonym, see damned if I do, damned if I don't.