Logan- You regret working for Abbadon. You had killed many people because of working for her. You especially regretted it when you were about to kill Logan, Abbadon behind you telling you to do it. You couldn't and turned on her instead.
David- You regret getting into the family business. You new the dangers of hunting and went into hiding to be with David. But even hiding couldn't keep you both safe. David wound up getting severely injured by a wendigo.
Merrick- You regret being a double agent. You hurt Merrick so much because of it you had to stop. You couldn't stand seeing him hurting and being distant with you.
Keegan- You regret being related to Castiel. He was always too protective over you. You felt smothered because of it,so you got angel warding on your ribs to hide from him to not feel smothered.
Elias- You regret dying your hair. You get hurt on every mission every time. Elias couldn't stand seeing you get hurt so he cut your hair short. You got used to your hair being short that you never let it grow out again.
