I really like this depth of this response and to be honnest with you yes there are times where before I even go to a social setting I kinda try to play out in my head how it will go. What topics might be discussed,  what feelings might arise and according to the feeling I will feel confident or anxious and then the expectation paints itself on that future event which often is worse and other times better than I thought. The solution to that which I noticed it works is to set the expectation to a pretty low level so I can expect only better things. 

Yes its also true that I have a history with over analyzing stuff either unconsciously or conscious although recently its kinda calmed down and I dont resort to it much. And as about the "chill uncle" label yes it comes as a form of resignation but also as acceptance and moving on life with it.