With regards to approaching women, you are in a kind of catch-22: you are anxious and insecure about talking to women, and so you avoid talking to women, but the only thing that will ever make you less anxious about talking to women is, well, talking to them. At some point you are going to have to push through those issues and put yourself out there. You might not like it at first, but eventually you will feel comfortable enough doing it.
And I totally agree with Manic: you should stop placing so much of your happiness and your life on someone else's shoulder. No relationship is going to survive if you start any potential relationship with this "the one" and the "missing part of my life pie chart" crap. Relax and try to learn from the failed relationships.
Finally, that last post of yours bothered me quite a bit. For someone who is so upset about girls not giving you a chance because of appearances, you are pretty quick to judge others based on appearances. You can't ask someone to go beyond your looks and get to know you when you are dismissing girls right away as "skanky looking," or immediately judging them by where they go to.
You can sit on your ass and wait for a girl who is pretty, smart and nice to look past your appearances, your insecurity and your anxiety to initiate things with you and be ok with this enormous burden of making you happy and complete your life.
Or you can go out and start living, giving people and places the chance that you want them to give you. It might be hard, it might require some work, it might even require professional help, but it really is your only reasonable option.
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