I once attacked my daughter Lucia by accident... I wanted to give her a gift, so I left-clicked twice...

My character pulled out his ebony sword and attacked Lucia...

I have gone into a brawl wearing the Ebony mail.):

I killed many friends with the Ebony Blade.

I chose the empire on my first playthrough and the stormcloaks on my second, when I had to betray Balgruuf and he said "and you? A Stormcloak? I thought better of you." I felt awful

I absolutely regret killing Cicero. I mean, his stuff is alright but frick, he was just a jester.

I killed Farengar Secret-Fire just to get the key to the Ebony Blade...

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Killing Anoriath as a possible radiant quest in the Dark Brotherhood. I'll happily off the jerks but Anoriath is always nice (and his bro's shop is a good place to offload loot).

Horseshoecrab

I chose the empire on my first playthrough and the stormcloaks on my second, when I had to betray Balgruuf and he said "and you? A Stormcloak? I thought better of you." I felt awful

Any time I do a Stormcloak playthrough it's a character based off a known rebel. Other than the ethnocentrism, Balgruuf is the other main reason I normally go Imperial.

Got screwed by the Ebony Blade. game crashes alot and death is usually immient from Alvor. Named my black cat: Alduin, the World-Nibbler, he will eat the world, one cheese puff at a time.

Moding The Elder Scrolls IV Oblivion.

on a sad note Alduin, The World-Nibbler has sadly past a month ago