I'd say deep down I do care what other people think about my personality anyway, who doesn't want to be liked? If I find out that someone doesn't like me, or whatever, I often ponder over it and think 'why'? However, it's daft to obsess over such occasions, because the times this has happened is usually when I have been drunk, loud and probably offensive.
Other things I don't give a shit what others think, but these things might not necessarily be about my personality.
I can't totally let go and be carefree of others opinions, I think I do care less than I did when I was in my teens/early 20s where image was maybe more important, or even stupidly living up to an image sometimes back then, which I wouldn't do now.
Certain people's opinions are obviously more important to me - family, close friends etc. - although, if I have an issue I find it hard to talk to my parents about it, I always want them to think all is okay, when sometimes it's not. I look at them and they seem to have their shit together, when I think of them at the age I am now they seemed to be far more advanced and successful in life, but I may just be dwelling on decisions I have made and paths I have taken.
On holiday there I kind of made friends with a German couple, we'd end up sitting together at the pool bar after lunch, chatting about music and drinking beer mainly, they were about 10 years older or so. On their last night I was supposed to meet them for dinner, I ended up ridiculously drunk and I have flashbacks of being in the restaurant, I'm convinced it ended on a sour note, but I don't know if this is just all in my head and The Fear is making me think that, I honestly can't remember the night. Point is, I'm never going to see those people in my life ever again, but I liked them and I was genuinely worried that I had somehow offended them and that they left thinking I was actually a dick, when we had been having such a good time the rest of the afternoons we spent together.