derpressing 

adj.

Carrying or resulting in a feeling of miserable dejection brought on by stupidity.

It's fucking derpressing that so many people think Sarah Palin is a viable candidate for president.

derpressing by Imperialist October 28, 2010

depressingly spicy 

When a situation isn't how you want it to be, but it benefits you.

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."

depressingly spicy by Catherine Dif January 30, 2019

Depressing Fire 

When your house burns down

Metaphorical for a bummed out feeling or attitude. Doesn’t refer specifically to a tragic event

Fuck, my break up with Triss has just been a Depressing Fire

Depressing Fire by 5YEARSgone December 28, 2019

This is very Depressing Alexa play Dame tu Cosita 

A depressing version of This is so sad Alexa play Despacito when it goes more sadder than before and this goes viraly dramatic over sad contents.

P.1: My brother died but what’s worse my cat died he got runned over by a car...

P.2: This is very depressing Alexa play Dame Tu Cosita.

This is very Depressing Alexa play Dame tu Cosita by R.O.B. The savage robot July 13, 2018

depressinating 

Anything simultaneously depressing and fascinating.

The custom built 8 foot limestone cross at Jenna Bush's wedding is just depressinating.

depressinating by s1wfor free May 18, 2008

Depressengers 

The team you join when you realize you are too fat, lazy and out of shape to be a super-hero and too stupid to be a super-villain.

"The Despicable Bulk. Whore. Can't-Man, Black Man/her, Fat Piggo, and small Dick Fury. Depressengers ASSEMBLE!"

Depressengers by GroceryClerk July 4, 2018

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