Caring too much about what others think of you, what you do what you say etc, can be crippling.
The basic anti caring mantra is, if you dont decide how to live, run your life, others will do it for you, subtely, covertly. you have become socially conditioned and pre programmed to take into account what others think, devaluing your own inner desires. psychopaths are great with womne and can be successful in life, work business...because they are pretty much 100% selfish, if you can call that success?
To stop caring what others think or expect wont happen overnight and even if it did you would freak others out completely.
start by making subtle changes in your mindset, be a little more assertive with your opinions and stick to them, its ok to have a diferent opinion/point of view, just be prepared to back it up.
as far as women are concerned, set yourself some standards i.e no fatties, tell people, this reinforces it in your own head. dont be afraid to upset people, dont be an ar$e about it and do it deliberately, be a little outspoken though, add a little shock factor, it better if you can back it up with humour.
this is your life, you arent going to be here very long, no one rally gives a sh1t about what you think/say do, you might p!ss one or two people off but life will go on, be brave, live your life they way you want to, do what you want to do, no fcucker is going to thank you for living the way they think you should.
always worth watching this too, the biggest battle = your life, apply it and use it
http://www.youtube.com/watch?v=WO4tIrjBDkk
one day you will be "too old", Im a bit like him, Im old, came into this late in life, wish Id started much earlier, nothing I can do about that now though except live the rest of my life the best I can