you 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.
See also: win
Farlex Dictionary of Idioms.

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
The American Heritage® Dictionary of Idioms by Christine Ammer.
See also:
  • (one) can't do right for doing wrong
  • (one) can't win for trying
  • drive (one) out of office
  • force (one) out of office
  • force out of office
  • give (one) (one's) head
  • give head
  • give somebody their head
  • give someone their head
  • cooking for one
References in classic literature
I suppose you can't help it, if it's not in your nature--but I WONDER you can't win the confidence of that girl, and make your society at LEAST as agreeable to her as that of Robert or Joseph!'
Agnes Grey
It joins such pearls of wisdom as: "You have to stand for what you believe in, and sometimes you have to stand alone," (Queen Latifah) and "The only one who can tell you 'you can't win' is you, and you don't have to listen," (Dame Jessica Ennis-Hill) in Go Girl (PS6.20, Wordery.com) a book of motivational quotes and tips for when you need a little boost.
READ IT
He said: "It's always good to be getting points, sometimes you can't win and you have to settle for a point.
Ayoze Perez aiming to keep on climbing in 2018 with Newcastle United; The Spaniard is positive that the new year can be a good one for the Magpies but knows it will be tough against the Potters
They will never win" Tobias Ellwood, Tory MP, who tried to save the life of a policeman stabbed during the terrorist attack on Westminster last March "Ageing is a fight you can't win, so you either lose with dignity or you end up looking like a circus freak" Broadcaster Graham Norton is no fan of cosmetic surgery
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