I think one underrated tragedy of Ice King's scars is that he probably took away Simon's sense of levity.
Like in his very limited appearances before Simon is consumed by the crown we see he's kind of a silly dude. In his introduction video, he only put on the crown in order to playfully tease his fiancee. Plus watching him make light of the loneliness and general misery for a young girl in a broken world. He was a dedicated man, who was generous and loved with his whole heart and threw himself one hundred percent into everything he did. He was also a fun lil guy.
But after almost a millennia of being a mad man, the brunt of every joke, someone who only existed as a broken caricature of himself and couldn't be counted on to take anything seriously, I imagine he was done with it. Now he wants to focus back on his academic endeavors, on his role as a father figure in Marcy's life, on being a proper adult. Any attempts to be silly could easily remind everyone - including himself- of Ice King, something he's eager to avoid.
So his jokes and jibes and general lightheartedness turned to sarcasm and self deprecating comments.
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[ID: a digital redraw of the scene where chuuya shoots dazai in the shoulder. on the top of the drawing is chuuya holding a guy to dazai's head in the red and grey hallways of the prison. on the bottom of the drawing is dazai's pained face. the gunshot is shown stylistically as hectic lines behind his bloody shoulder. over the image is half a quote from goncharov that reads 'if we really were in love you wouldn't have missed.' the signature says dandelion-roots. end ID]
This quote from Goncharov (1973) in relation to soukoku has been haunting me from before I even got to that scene in the anime (the full thing is: Katya- Of course we're in love, that's why I tried to shoot you/ Goncharov- If we really were in love you wouldn't have missed). Violence as a tool for communicating emotions, especially love and hatred, especially love and hatred makes me go feral- how could I not think of the iconic quote that says that katya's miss was a sign of a lack of love/a fake love when chuuya didn't miss? Just... losing it over here.
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