(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 Mary'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.