Your post is something I can HEAVILY relate to, Edahn. And I'm still trying to pinpoint my problems with this as well.
One of the things I've considered is that part of my need to please people and make them like me has stemmed from specific negative childhood situations. I've noticed on looking back into the past that there were various instances where I'd get an unexpected and unintended negative reaction from someone - relatives and friends. For example, I'd be making a harmless joke, or just trying to be friendly when all of the sudden someone would blindside me with an angry reaction that I felt was out of proportion to the situation. Or as many children do when they want to be "cool," a person whom I thought was my friend would turn around and start being a jerk the next day. I never did that to people as a child - I was pretty sensitive and empathetic - but when people did it to me I couldn't make head or tails of it, and it scared me. It scared me that I could just be minding my own business, and someone could suddenly come at me with a negative reaction that I never would have expected. Kind of like when you're driving along at the speed limit and some Jeff Gordon-wannabee comes flying past you flicking you off. It's like - what did I do to provoke that (besides driving the speed limit, which isn't some heinous crime)? The possibilities for interpersonal chaos terrified me from a young age. The fact that I can't predict the behavior of others, and that just because I act one way doesn't mean the other person will follow.
I believe these experiences might have something to do with my seeking approval from others. By being nice to people, I'm trying at all costs to avoid those unexpected negative reactions. I'm charming to disarm. I see negative possibilities in every interpersonal relationship, and I become overly paranoid, seeing negatives where there are none, blaming myself for things that might have more to do with the emotional state of the other person.
I too was a pleaser as a child - I wanted teachers to respect me and not treat me like an idiot. Trying to equalize authority is still something I do now.
I genuinely enjoy being around others when I feel a level of safety has been reached; I love that feeling of togetherness. But till that point, I can be very socially anxious and overly paranoid about the intentions of others. I hope we can all get ourselves on to a path of training to stop this behavior, because it does suck.