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.