I think people tend to be more shy when they are 'out of their element' and more confident when they are in a position of knowledge or power, however minor and arbitrary. What activities does she like to do? Is there a game she is good at? ask her to teach you how to play. is she an art lover? Have her guide you through a museum. Does she like to cook? ask her to teach you how to make scrambled eggs. If she is also physically shy, and things progress well, having her teach you how to ice skate/roller blade/dance/golf/whatever can be a great way to initiate physical flirting, since she'll need to hold your hand/help you off the ground/whatever.
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