Normally a guy who thinks he isn't a hipster, or a tool, but listens to a lot of Spotify playlists called Indie Electronic, plays Ultimate Frisbee, and is not able to hit on girls.
"Wow that guy is super hipster, but also is a complete ass"
"Yeah he's a hipstertool"
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.