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Getting better at dating?

There's a woman who I'm becoming well acquainted with and I think she might like me. But I'm a pretty quiet individual. I'm not the easiest person to try and talk to. I've been told by some women that I'm difficult to read and it probably drives a lot of the women I know nuts. I'm not trying to self-deprecate, and I don't necessarily hate that about myself, but I'm aware that this type of attitude doesn't really help in the dating world. For example, this girl and I were leaving a friends house. Typically one of our other friends has dropped her to and from his house, but I think that maybe this time she was waiting for me to ask, but I stood there staring at my phone like a dufus. By the time we were heading to our cars, she told my friend that she was going with him and he seemed a little surprised. She then said bye to me in a sort of passive aggressive way. I could be reading into this too much, but the point is I like her. I'm just not much of a conversationalist. How to do I work on this?
Getting better at dating?
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