Most Helpful Guy
Shy people can be bery difficult to figure out if they like you are not simply because they can be so good at hiding their feelings. Smiling and nervousness is a good sign.
As a shy person myself, I can say that once you talk to someone a little more conversation flows easier and becomes less awkward. He probably won't find too many things aggressive unless you go completely over the top extrovert on him. But don't be afraid to make the first move! Since he is shy, there is a good chance if you wait for him to make a move nothing will happen or it will happen verrry slowly.