Brown people who work off commission at stores like Futureshop and A&B sound - instead of helping out one customer at a time - they will bounce from customer to customer trying to maximize their profit. Hence 'Double'-deep.
"Fuck, Gurpreet is such a doubledeep, he totally jacked my sale".
"Rahul needs to learn to stick to one customer at a time, that dude is such a doubledeep".
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.