February 15, 2014 7:48 PM EST
Well, I roleplayed Illia as one of my characters step-niece (?) and I killed her repeatedly. So ya kinda felt bad 'bout that.
Also I soultrapped the emperor on one play through and on another playthrough I casted a frenzy spell on him after he said, "I will not fight you."
I do feel bad that my favorite Roleplay character, Gorthalyn, has the Ebony Mail when he is supposed to be morally good.
EDIT: Also forgot to mention killing Paarthurnax, even my cruelest characters (I have very evil ones) would regret that.