<human>: When I first started high school, I was *really* shy. I'm a senior now and I've opened up a lot since then. I'm generally considered reasonably outgoing and talkative, if still slightly introverted. 

[Recently, I started chatting \(online\) with a friend of a friend \(Well, one several-hour session so far\).] At first I figured from the way she was responding that she wasn't interested in talking to me, so I started to politely extract myself from the conversation.
She protested, though, saying I should stay and apologizing that she was just shy and not very good at talking to people she doesn't know. 

This got me thinking that, while I'm not really very shy anymore, I still have *never* knowingly interacted with someone more shy than I am. It was almost a revelation where I suddenly knew what it was like from the other point of view. 

I'd like to get closer to her but I'm unsure how much of the talking I should do and how often I should try talking to her. I don't want to come across as being overwhelming.
In your experience, what's a good way to guide the conversations and hopefully help her open up to me?

Can you condense the text into a few key points?
<bot>: First time since coming out of my shell that I've ever talked to anyone who is very shy. Want to direct the conversations but unsure of how much is too much / where to go from here.