I personally find shy girls kinda cute. Maybe the question you should ask is: "How can I be myself and still get what I want?"
You're a girl so you've got it easier than a guy who's shy. Try meeting a guys eye and smiling. If the guy's interested he might approach you. Practice this skill first. Just try to meet peoples eyes when you're out. You don't have to smile or say anything. Then, when you're ready start meeting their eyes and smiling. Next step might be to say hello. Chances are the other person will say hello. You can just walk on after that if you want. If you find it too threatening to talk to people your own age try speaking to old people or children. Take gradual steps until you're a little more confident.
What do you say? Go along with the conversation. Ask him questions about why he's there, what his interests are. Ask him about his watch if it stands out.
Or you could wear unique ear rings or a necklace that stands out, which could give him something to ask you about. You could say you're shy, which might encourage the guy to take the lead more in the conversation.
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