I'm a little bit similar -- with my mom it was easier to just be inconspicuous and not to share any of my ideas or feelings because there was no telling how they'd be received. So now when I try to fit in with people I'm just sort of ... lost. I have very limited skills and end up just screwing up. I either sit there like a bump on a log with nothing to contribute, or I try to punch up my self-confidence and put myself out there--but in these cases I feel I usually make a big loud ass of myself, monopolizing the conversation, etc because I just don't know what the hell I'm doing! I tend to avoid parties or large gatherings because I just don't know how to join in the little clusters of group conversation ... last time I tried was a year ago, and later my husband told me he noticed someone got really offended and hurt because shortly after we got there I tried to join her conversation and in the process I "interrupted" her when she were talking. It was a loud bar, I couldn't really hear their conversation as I approached, and I was just trying to say hi so I wouldn't be standing there awkwardly by myself. I don't feel bad because this particular person talks over people all the time, but it doesn't change the fact that I only did it because I felt lost and had no idea what else to do and was ultimately unable to participate fully in socializing the way others seem to do with no problem.
I also have a tendency to be accidentally hurtful -- like I try and lightheartedly tease people or engage in what seems like fun mutual ribbing when other people do it with each other, but somehow when I do it, it doesn't quite work out.