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.
Nickname for someone who is constantly optimistic and seeing the bright side of things, the glass half full, and forces her happiness and optimism onto others.
A person who is optimistic about everything beyond logic and reason. The optimism level of this person surpasses reason and is a way to see everything as glass full.
Man his girlfriend left him for a rich guy, but he still thinks he gonna get her back. He's a proper delusional optimistic