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Culture Barrier
I'm a 19 year old college student living in upstate New York. I spent my formative years hitchhiking around dirt-poor third-world countries, and rarely got the chance to date. Now that I'm back in the US, I find myself rarely getting past 'friends' status with women.
It's not a problem of shyness; I have a healthy self-esteem and am very outgoing. Trouble is, I was never trained to make moves on a girl, and its becoming a bit frustrating. I'm 'best friends' or 'the most interesting guy' to more beautiful chicks than I know what to do with, and I still go home alone at night.
Its getting to the point where women spend money on me (usually in the form of pot) to hang out, and yet I can't get laid for the life of me.
This is getting ridiculous.
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You have to learn how to drop hints, flirt and make moves on girls you are interested in. Since it seems like you have no shortage of girls surrounding you, you should start experimenting and testing things out. You need to find out for yourself what works for you given your personality.
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You can be the most well traveled and interesting fellow in the world, but unless you add some sort of sexuality to your communication, you will remain "the most interesting guy" and not much more.
Mish has suggested some great places to start, but in addition, why not go out with your female friends and pay attention to the men who are successful with not only your friends, but other women in the venue?
Use your outgoing personality to meet and befriend these fellows and then learn through observation.
Apply what you learn and realize new skills through subsequent successes and failures.
~Sphinx