A phrase meaning that things would be going great for you if they weren't going so badly.
"Well, my girlfriend dumped me, my dog died, I got fired from my job, I went to grab some fast food to make myself feel better and on the drive back I got a flat tire, and when I finally get home I realize they screwed up my order."
"Damn, you can't win for losing."
by Kraas March 5, 2008
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When you win something but , winning means you lose either psychologically emotionally physically financially, anyway that negatively impacts you.
You do the dishes cuz your parents told you to and ,then when you're finished they yell at you for doing it wrong even though they didn't tell you how to do it in the first place ! Man you can't win for losing
by dragonboy8586 October 16, 2019
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A TERM THAT YOU'LL USE IF YOU OUT SMART OR CHEAT SOMEONE.
YOU SO DUMB YOU DON'T 2 + 2 SO, I WIN YOU LOSE
by TAYLORGANG TAE April 28, 2011
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Is a moment when a person has beaten the odds but has still lost for not seeing the bigger picture.

Shorten version(s): EWUWUL / WBL
You have lost this battle.
You have defeated only a small portion of our army.
Even when you win you lose.
by BrokenDragon January 10, 2016
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A more serious incarnation of the commonly used phrase "you win some, you lose some". "You win a few, lose a lot" is meant to express the feelings of constantly losing or being screwed over despite trying your best.
Guy 1:"Hey man what did you end up getting in your math class?"

Guy 2: "I bombed the final and got a D in the class."

Guy 1: "Damn well are you still going out with that girl you met a few weeks ago?"

Guy 2: "No she ended up going back to her ex. It's like they say you win a few, lose a lot."
by Jonan2012 December 21, 2011
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An annoying trick that your best friend likes to pull on you, hoping that you won't realize that both outcomes are in their favor
by ThunderSpider July 17, 2017
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The result of a possible win-win scenario in which the clear beneficiary of the win-win scenario fails to keep their end of the bargain, resulting later into a win-lose scenario.

Commonly found with people who fail to transition a informal verbal agreement to a formal written agreement, backstabbers, double-cross someone, or dealing with someone with a "do nothin', get everythin'" mentality.
1.) When Paul failed to wash the dishes all week after his father let him go to a party the previous week, his father realized that he was a victim of win-lose bargaining.

2.) Mike had been involved with some win-lose bargaining when he and Ken agreed to split the bill only for Ken to leave without notice, leaving Mike to pay for the large meal.

3.) When someone agrees to give another head after they themselves have been given head, but then leaves, the giver of head is on the losing side of the win-lose bargaining.
by lastray February 3, 2011
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