Popularized by the indie game Dwarf Fortress, "losing is fun" refers to the inevitable destruction of your fortress, wether by goblins, elves, kobolds, humans, demons, and more! It really is what keeps many players going, wondering what will destroy their new masterpiece.
Me: Okay, that's another 8 forts lost in the last week. Let's look for a nice, quiet spot to make my new fort. Oh! That'll work! >click<
Game: UNICORN INVASION!!!
Me: AW, COMON! *Sighs*. Losing is Fun, and all that.
Two days later: *Mumbling incoherently into a corner
Game: UNICORN INVASION!!!
Me: AW, COMON! *Sighs*. Losing is Fun, and all that.
Two days later: *Mumbling incoherently into a corner
by Guess_Who_Else October 22, 2011

by Justin Ehlert January 7, 2004

An NBA player named Kawhi Leonard was famous for being emotionless and not talking at all, but when a reporter asked him to describe himself during his first press conference as a Toronto Raptor after all the silence drama in San Antonio, he described himself as a "fun guy," which, combined with his laughter immediately after, blew up in the basketball community and made Kawhi Leonard the NBA meme of the year.
by urbanfunguy March 29, 2019

by zoomzoomthefastestniggaalive September 10, 2019

by goldenrule October 16, 2020

"Dude, I went out with Kathy the other day. We got busy back at her house and she totally sucked my fun plums while I whacked my weasel."
by dw8177 April 25, 2017

by Camthefish January 6, 2014
