I've never posted here before, so go easy on me if i'm doing this wrong.
I just watched Death Takes a Holiday and something stuck out to me. There's a moment when Alastair has Dean and Sam pinned to the wall in the funeral home and he's doing his usual villain bit, taunting them going on about breaking the seals, and Dean makes the remark "You're going to kill a reaper with that?" refering to Alastair's scythe. "It's a little on the nose don't you think?" After Dean's initial questioning of his weapon choice Alastair's expression really seemed interesting to me because it wasn't what i had expected. I thought he was going to look either annoyed or be dismissive of Dean's smart alec remark. But instead after Dean says "You're going to kill a reaper with that?" Alastair looks confused and almost eager to hear Dean's reasoning. And even weirder when Dean says "It's a little on the mark don't you think?" He actually takes Dean comment into consideration and feels the need to justify his choice to them.
This little exchange made me feel like Alastair sees Dean as an equal in some respect. They were both torturers in hell, Alastair of course was the big boss torturer, but in a weird way they worked together. The shows been making me wonder what their relationship really was in hell. Alastair did tell Dean he had promise. And he mentioned that Dean can't get him out of his head, which seemed to hint at some connection between them.
I definitely don't think they were best friends in hell or anything. I feel like demons can experience some human emotions because they were human once, they feel anger and hate and need and that's what fuels them. It can be assumed if they do feel other emotions like empathy or friendship it would be in a extremely twisted and negative way.
Just to clarify i'm not implying that Dean and Alastair had a romantic relationship, i'm just wondering if they had a boss/employee or possibly a mentor/student relationship.
I don't know if i'm allowed to do this but i'm going to pose a question and i'd love to get some peoples opinions in comments here.
Did Alastair feel some twisted form of friendship or mentor relationship with Dean in hell?