Oh well, I know I made it at least subtlely clear that I wasn't looking for a "friend" and physically I'm in her "league" so she could just very well be very shy. Or, of course, she could just not be very interested and think I'm an #######. Either way is fine - she's very nice but I won't be heartbroken if I have no contact with her again. After the date I did get a little frustrated because I felt I couldn't take ahold of the situation with her and got no signals
Its been a long time for me, but after thinking about it all I can come up with is to push their envelope. This will obviously bee difficult for a self described shy guy like yourself, but its some advice, YMMV.Start asking her direct and probling questions to get her out of her shell and raise the sexual level of your meeting. Start with subtle "Damn, that guys a good dresser ... do you think he is hot? Would you date a guy like that?" Maybe move to "That girl is ok, I think if she worked out more like you do she would be better off". After some time, move to first date questions "So do you ever kiss on the first date? Im going to be pretty angry if I dont get a first date kiss. For me, its just about a given ... just wanted to let you know." Judge her responses, does she play it off, give into it, or abrubtly respond with "No!" Move to something a little more personal "Do you date a lot? What kind of guys do you go for? Im not sure I fit that mold, why exactly are you out with me?" and "Are you more of a short fling with guys or push into longer relationships? Whats the longest relationship you have been in? Wow, he put up with you that long ... just kidding".
These questions are to elevate the sex level of your date. Take her out of shy shell and force her into either defensive or agressinve front. It will be pretty clear how she wants herself to be perceived. Remeber, most (sober) women care lots about how they are perceived through their answers. If she wants you to think she is a shy prude, you will know. If she wants you to know that while she is a bit shy, she is a muther####ing lynx ready to pounce on your bones ... she will let you know.
Good luck

JAA, I think you usually give great advice, but I can't agree with this bit. If a guy went along most of the lines you've suggested, most women would think..."Damn, that guys a good dresser ... do you think he is hot? Would you date a guy like that?" - Is this guy gay?
"That girl is ok, I think if she worked out more like you do she would be better off" - We've gone over this one before, but criticizing other women is a no-no. Makes a girl wonder what you're saying behind her back and just generally makes you look like a cad.
"So do you ever kiss on the first date? Im going to be pretty angry if I dont get a first date kiss. For me, its just about a given ... just wanted to let you know." - Said in the right way, you could pull this one off.
"Do you date a lot? What kind of guys do you go for? Im not sure I fit that mold, why exactly are you out with me?" - Sounds way insecure.
"Are you more of a short fling with guys or push into longer relationships? Whats the longest relationship you have been in? Wow, he put up with you that long ... just kidding". - Might be OK if you say it right.
I realize that you didn't mean these exact phrases have to be used, but here's the problem, and I do NOT mean this as bashing Woz - Woz probably couldn't pull these off. He's stated that he's shy, and we know that he is definitely not good at improvising. I'd just be worried that he'd decide to try and it would be a disaster. Otis could probably get away with the two that I've mentioned you'd have to say right, because he'd say them in a lighthearted manner. Woz is generally more serious and sensitive, which I do not think is a bad thing, but just means this approach probably wouldn't work for him.
Woz, I think you'll just need to be a little more patient. Sounds like you had a pretty good time with this girl, and hopefully you'll just both be more relaxed on the next date. She could also be picking up your vibe - we know you were nervous about this, too, and not sure you wanted to date at all - and reacting accordingly. Relax and have fun!