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I say that you go out and try it, like many other posters have said. It may suck at first, but the more you do it, the more natural and relaxed you'll feel. It's like anything in life - it takes practice.
Just recently I went out one night and had a guy approach me. He was nice enough, but was very direct in his advances, mainly because he was way too drunk. So that is one lesson - don't get too drunk or you'll probably ruin your chances. Another thing that turned me off was that he didn't have anything to talk about with me, didn't really try. I like a guy who has something intelligent to say and at least appears interested in who I am, not just that they like how I look and act.
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Whether we write or speak or do but look
We are ever unapparent. What we are
Cannot be transfused into word or book.
Our soul from us is infinitely far.
However much we give our thoughts the will
To be our soul and gesture it abroad,
Our hearts are incommunicable still.
In what we show ourselves we are ignored.
The abyss from soul to soul cannot be bridged
By any skill of thought or trick of seeming.
Unto our very selves we are abridged
When we would utter to our thought our being.
We are our dreams of ourselves, souls by gleams,
And each to each other dreams of others' dreams.
Fernando Pessoa, 1918
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