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depressingly optimistic 

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.
depressingly optimistic by Vully November 4, 2011

Cynically optimistic 

When you're really negative about something you're actually looking forward to.
Marriage is the biggest mistake I can't wait to make. It's the only thing I've ever been cynically optimistic about.
Cynically optimistic by Sanityfan November 29, 2015

miss optimistic 

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.
miss optimistic by missnegative December 7, 2010

delusional optimistic 

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

cautiously optimistic 

A euphemistic (yet silly) way of saying "worried". Most often said by those on national news networks.
Joe Boorman was cautiously optimistic on whether his wallet would be found.

terminally optimistic 

Men aren't pervs, they are just terminally optimistic.