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you win some 

Short for, "You win some, you lose some". Usually employed when a situation or endeavour doesn't pan out in a auspicious manner in spite of a party's best efforts. Interestingly enough, despite the inclusion of the word 'win', ironically the phrase is often intended to console a loser.
"Wow, you spent $700 on that date and she went home with the waiter. Ah well bro, you win some..."
you win some by redgyul October 10, 2004
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winsomeless 

a big black guy
winsomeless fucking sucks
winsomeless by JayPlayzz December 24, 2020

Win some medals

New code word for smoking weed, thanks to Michael Phelps, who won a record number of gold medals while blazed.
"Hey Johnny, wanna go win some medals?"
"Fo sho, let me go get my bong"
Win some medals by Dont Smoke Dope February 26, 2009

winsomnia 

Insomnia caused by staying up into the wee hours of morning to watch a game that starts late or goes into overtime, or both. Most commonly experienced by extremely devoted fans in the Eastern Standard timezone whose team is playing on the West coast. Winsomniacs are known to obsessively deny themselves sleep until they know the outcome of the game, driven by the hope of witnessing a win.
"Uh you're wearing two different shoes today."

"Yeah.. Wings finally turned up the heat in the third period, and it was winsomnia from there on out. I don't even know how I got here."
winsomnia by gopixelsgo May 12, 2009

You Win Some, You Luge Some 

A snarky version of "You win some, you lose some." Popularized during the 2010 Olympics when Nodar Kumaritashvili, a 21-year-old Georgian luger, was killed in a training crash. The video was widely distributed and fairly explicit, as he crashed into a steel pillar at nearly 90mph. The event spawned numerous internet memes.
Canadian Prime Minister: We spent over $100 Million dollars preping athletes as part of the "Own the Podium" program for Vancouver. What is the status of our goal?

Canadian Olympic Committee Chair: We have roughly 1/3 the medals of the USA. We are tied with South Korea, a country that does not technically have a winter.

PM: Well, "You win some, you luge some."

winsomezebra7 

winsomezebra7 is a fucking man slut that fucks other people including kids
1. Have you heard of that slut winsomezebra7?
2. I have a bad feeling about this I feel like winsomezebra7 is gonna break down my door and rape me
the act of three or more people playing the nintendo wii.
John: Hey, Timmy, you down for our wiikend?

Timmy: Yeah, but you cool if Jen comes?

John: Hell yeah! Wiisome!
wiisome by karaoke party bus May 28, 2007