(one) can't win(redirected from he can't win)
(one) can't win
1. One is unable to find or create any success; one has been constantly and 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.
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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.
The American Heritage® Dictionary of Idioms by Christine Ammer. Copyright © 2003, 1997 by The Christine Ammer 1992 Trust. Published by Houghton Mifflin Harcourt Publishing Company. All rights reserved.
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.
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