One of the main characters in an unknown comic strip called We Are The Bored
Always known to be somewhat sarcastic to his friends and others around him. Despite his last name and it's true meaning, he isn't exactly what you'd call a 'Simpleton' although on certain occasions he has been known to be gullible
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.