Lose-Lose Win-Win 

1. Think of something you know you need to do, but that you don't want to do.
2. Stop waiting and go do it.
3. Don't listen to me.
4. Don't let me tell you what to do.
5. Do what you want.

And that's an example of a lose-lose win-win.

Lose-Lose Win-Win by Ferington January 27, 2021

win-lose bargaining 

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.

win-lose bargaining by lastray February 23, 2011

Even when you win you lose 

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.

Even when you win you lose by BrokenDragon April 20, 2016

I WIN YOU LOSE 

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

I WIN YOU LOSE by TAYLORGANG TAE May 19, 2011

heads i win, tails you lose 

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

Let's flip a coin, heads I win, tails you lose

heads i win, tails you lose by ThunderSpider July 23, 2017

You win a few, lose a lot 

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."

You win a few, lose a lot by Jonan2012 December 25, 2011