@hey-there you either gotta get lucky or form a bond that will eventually lead up to it. Either way you gotta get past that shyness. Push past it. Force yourself to be more social. Smile more often, look like the kinda person someone would enjoy talking to. But try not to look or appear creepy. I was shy before and as I started trying to change that i might have said some awkward stuff. Even if you do you can turn back, you mess up it's a learning experience. Eventually you will get more smooth at engaging in social conversations then from there it's about being in the right time and place.