Travis, I can definitely relate to what you describe. Although I'm feeling better about life now, I went through a period where I felt as though my inner fears would always hold me back from going after the things I wanted. *hug*
When it comes to approaching women, it might help to keep in mind that women have insecurities, too. These days, I usually feel fairly attractive, but in high school, I thought of myself as socially awkward and a dork. When my ex-boyfriend asked me out for the first time, I said no, not because of anything to do with him, but simply because I had never dated anyone before, and I was afraid to jump into something new. Eventually, he asked me out again, and we ended up dating for close to three years. So, I can say that dating really does get easier with time.
Also, keep in mind that women don't always equate hesitancy and shyness with a lack of confidence – some women find shyness attractive because they associate it with gentleness and sensitivity (In fact, that's how I'd describe my attraction to my current crush! ^^

. Many women feel more at ease with a man who's willing to show a bit of vulnerability, and the fact you were able to make this post shows that you have that quality. If you can show a sense of humour about yourself, that will help, too.
My practical suggestion for approaching women is to put less pressure on yourself: you might tell yourself that your goal is to strike up a pleasant conversation with an attractive woman, and that if it leads to a date, that's a bonus. Good luck!
Modifié par jillabender, 18 juillet 2012 - 02:43 .