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22.
YOLO is a way for people to simplify metaphysics and the existential meaning they wish to bestow upon life into four letters that allows them to bypass deep thinking in order to justify their actions relative to the fininteness of their lives. They don't allow themselves to think about the emotions connected to this objectification of self and the consequences associated with their actions, thus denying their essence of being in favor of a more short term "live as if you will die tomorrow" philosophy that does not actually lend to the true metaphysics behind YOLO; only scraping its surface.
Person 1: "Dude I can't possibly grasp my purpose in life. Why am I here? Why are any of us here? What am I supposed to do with my life?"

Person 2: "Don't worry dude. Just have fun! Let's go have unprotected sex and I'll cum in your mouth! YOLO!"
by pairagreenegg December 22, 2012
 
23.
YOLO, short for "you only live once," is an Internet phrase that obtained a large following in late 2011 and early 2012. It used to be used to express appreciation of life's little things and opportunities, but has since been butchered by being used with any action or phrase.
"omfg lol just killed a homeless guy for another cardboard box #YOLO"

"lmfao i want to see if i can juggle soap in prison and get away with it!!!!11!1!1!!!1! #YOLO"
by CipollaM926 March 27, 2012
 
24.
You Oughta Look Out
YOLO, say no no.
Isolate yourself
and just roll solo
Be care-folo
You oughta look out
also stands for YOLO.
by The Last Dalek January 28, 2013
 
25.
The most annoying acronym in the entire world. It's the most commonly used acronym of 2012. It was used by terrible music artists "Drake" and "Lil Wayne" that blew it up to a worldwide status. Most people that use Yolo are the most annoying kids around and listen to crappy poser rap music and couldn't even tell you what Tupac's record label was. People that commonly use Yolo are annoying as hell.
In a High School Classroom Setting

Person 1- Yo, are you going out drinking tonight?

Person 2- Of course dude, YOLO!

Person 3- Wow...

Person 4- You are so annoying I want to punch you in the face now

Person 5- Shut the F**k up.
by fuckyolo May 02, 2012
 
26.
An invitation for one or more person(s) to participate in anal sex.
Jeff: Hey, Janie. Yolo?
Janie: Yeah, come over at six and bring extra towels.
by The Impossible Derek March 19, 2012
 
27.
An acronym for 'you only live once' used by drake. Overused. Mostly used by attention seeking teens.

More modern uses of the acronym are:

You obviously love oreos
You obviously lack origianality
You only love once
You only lick omar

OLOY: only losers obey yolo
I'm gonna jump out this window #yolo

Just missed an exam and may possibly live the rest of my life as a hobo #yolo

Walked into a wall #yolo
by RandomnessIsKey March 22, 2013
 
28.
it is the most fucking annoying word in the world. people hate it. it is gay.
Guy 1: Yo sup

Guy 2: SMOKED A JOINT, YOLO

Guy 1: Fuck you
by TheWildGareBear June 20, 2012