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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.

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

Prousapointed 

The combination of being proud and disappointed at the same time.
I was very prousapointed in her.
Prousapointed by SnowBleper September 4, 2020