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Is there some extra trick to spreading holiday cheer in the slums?

I've beaten every encounter available in there except the guy with the quest marker, but he still gives the same responses as before I picked all those fights (including not accepting me trying to pick a fight with him), and I'm wanting to move on in the main story, but don't want to push too much further before finishing the holiday quest, since I think there was something about locking me out of finishing it if I do get past a certain point in the main story?

buy a punk outfit in gear shop 

Just tried it with that outfit equipped, but still get the same stonewalling dialogue; is there more to it that I'm missing?

did u give throb a hat he and where the punk set then talk at night

(+1)

Do you happen to use the skip mode? There's a bug where the combat encounters don't count with skip mode.