I'm going to be honest on this one. From ruining wedding days to killing older women, I didn't feel sorry or guilty for a second.
I had my reasons to join the Dark Brotherhood. I knew their rules. I wouldn't even hesitate if they told me to assassinate a friend.
How about you guys? Am I the only cold hearted killer here?
Nope, you're not the only one.
I've been right there with you since The Elder Scrolls games allowed us
to join an Assassins Guild. I never found out how to join it in Daggerfall, but in Morrowind I was a God amongst the Morag Tong. In Oblivion, I was the best Listener that they'd ever had, and it repeats now in Skyrim.
I love the Dark Brotherhood, I love the contract missions, and feel zero remorse or regret for what I do when on a contract. There was even a point when I had to hunt down the Chef in Markarth in order to find the location of the Gourmet. It was two in the morning, and while the Chef was sleeping, his two "assistants were still up and running around. So, there were three Souls sent to Sithis that night.
Loose ends and all that...

I love the Dark Brotherhood, and I love the Elder Scrolls!!!