you can't win

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(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.
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
References in periodicals archive ?
What I've found with lawyers is you just can't win, Button (above) has found that by driving cars not made by Brawn he just can't win.
YOU just can't win. An unhealthy slimming diet can affect looks as well as health.
With some people you just can't win. John the Baptist's opponents accused him of being demon-possessed because of his asceticism and ruddy appearance as well as his diet and "hangout." Jesus' opponents accused him of being a glutton and a drunkard because he enjoyed feasting (with the "wrong" kind of people).
Now the taxpayer pays for the huge legal expenses to inquire into this corruption - you just can't win.
He may not be paid very much, but at least the lad's learning that sometimes in life you just can't win.
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