A Gliding Monkey is a guy that is stupid enough to reject multiple instances of sex with a beautiful girl and instead choose a one night stand with said hot girl. (It is not because the girl rejects him due to bad sex, this is referred to as a Disgraceful Dick, it is the man's decision in the case of a Gliding Monkey)
What kind of dumbass would give a Gliding Monkey to Carly, with an asslike that.
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.