Person 1: "They don't have the expensive top I wanted to get in my size. It's so depressingly spicy."
Person 2: "Yeah you really wanted it but you didn't need it and you'll save your money."
Depressing, yet somehow optimistic. Typically used when something bad has happened and a pathetic attempt is made to be optimistic about it. It often leads to feeling more depressed.
This would be depressingly optimistic:
Someone you've had a crush on that you couldn't work up the nerve to talk to dies. Trying to be optimistic, you tell yourself, "Well, at least I don't have to stress over trying to ask her out.". Depression sets in when you realize how much you wanted to try.
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.