Look, this is the way to do YOLO.  All of you who are like, "omg, got a test tomorrow but I'm drinking 5 beers tonight, YOLO!" that's wrong.  Your use of YOLO is bad, and you should feel bad.  There are only 2 times where it is not corny to say to YOLO.

1) While doing something so random or ridiculous that you'll probably only do it once. For example: Doing a jump foot touch while being held by two cops for streaking at a Red Sox game. YOLO.

2) While doing something so mundane and ordinary that there would be absolutely no reason to say YOLO.  For example: Brushing my teeth with Colgate Total. YOLO.

So there you have it kids, those are the rules.  Also, remember to get as specific as possible for full effect.