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Proudappointed 

When you are proud and disappointed at the same time, when someone does something you shouldnt be proud of but for some reason you are.
Teila robbed a bank, but she gave me money, im proudappointed.

Prousappointed 

For when you're disappointed in someone but also slightly proud
You: I thought better of you honestly, I'm quite prousappointed in you
Friend: For the love of god please stop with the urban dictionary words
Prousappointed by Emosaurus Rex February 17, 2019

Proudappointed 

Proudappointed

/praʊdəˈpointəd/

adjective

Combined state of mind due to someone having fulfilled a goal or dream in an unacceptable method.
"I got my Waifu home safe but couldn't wipe after shitting because I was guarding her."

"I'm proudappointed Penis Jeff."
Proudappointed by PenisJeff June 10, 2015