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.