Commonly refers to What are you wearing? It is often used as a means of getting into ones head furtherly into ones pants. Often unsuccessful, but still funny as shit.
Guy 1: "Dude, WAYW?"
Guy 2: "Zebra thong with pink stripes man!"
Guy 1: "High Five!"
Guy 2: "Lets make out."
Any individual who thinks for themselves, and laughs in the face of authority. Someone who goes against the grain in several aspects of their life, and is publically chastised for doing so. A person who refuses to bend to the conventions of society. A natural born leader. Unconventional in their wisdom, and accutely aware of their surroundings at all times. Often alienated for being so.
"The Motorcycle Boy, in SE Hinton's novel 'Rumble Fish', was definitely a wayward son."
You are a wayward. You are lost, but you are also searching for yourself. You can't control your behavior. You wander around searching for something, but you can't quite find what it is. You could spend years or even a lifetime searching for this thing, but you being a wayward must keep wandering. As a wayward, you will never be able to sit still, you have to keep moving, but don't let that stop you. One day you'll pass on your wandering spirit onto the next, and you'll finally find what you've been searching for all along.
While our lifespan is the number of years we will live, our healthspan is the number of healthy years we will have and our sexspan is is the number of years we will continue to be healthy enough to continue having an active sex life.
A lighthearted reaction upon receiving disappointing news of some sort. Usually something that isn't a particularly a big deal, esp. when it primarily affects someone else - sort of a mild schadenfreude. Sometimes doubled or tripled, and possibly said in a sing-songy voice for added comedic effect to imitate a muted trumpet, which is how the meme originated.