Dating people who are currently overweight, but have some beautiful features and, under the right circumstances including weight loss, has the potential to become very attractive and at that point out of your league. Although there is a very small possibility of this, a penny stock dater has decided to assume the risk and invest without any guarantees.
"Yo Bob... Remember Lisa last year, chubby but with the cute eyes? check that bitch out now after losing 40lbs.. Once she went for 20 cents now going for a Benjamin these days. Your ass should have invested in some penny stock dating when you had the chance."
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.