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Get to know her as a person and friend. Show interest in learning more about her, and gauge her willingness to open up when determining the direction of your relationship. Your goal is to make her comfortable with you as a friend, with no pressure or insinuation of anything else.
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Ask questions about things she seems interested in. For a shy person, it is often most easy and comfortable to discuss things they are passionate about.
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Realize that the woman may feel intimidated by dating. Shyness prohibits being comfortable in certain social situations, and by its nature, dating is a social activity.
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Be reliable and trustworthy. Important attributes for her to accept you as a friend, these traits are even more important if she is to consider a romantic relationship.
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Listen well. If you truly hear what she is saying, you will get to know the intracacies of her as a person better.
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Follow her lead. Note her levels of comfort, and if she begins opening up to you, you are on the right path. Your knowledge of her as a friend will help you to decide when the timing is right for approaching asking her out on a date
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Ask her to dinner or to another activity where it will be just the two of you, but don’t create pressure by making it formal or referring to it as a date. Simply admit you’d love to spend more time with her and see what happens.
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