(one) can'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.
See also: win

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.
See also: win

I, you, etc. ˌcan’t ˈwin

(spoken) whatever you do, you cannot succeed completely or please everyone: If I spend time with Phil, Jane’s unhappy. If I spend time with her, he’s jealous. I just can’t win. ▶ ˌno-ˈwin adj. (of a situation, policy, etc.) that will end badly whatever you decide to do: They’re in a no-win situation at the moment. Whatever they do, someone criticizes them.
See also: win
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