I've been seeing this girl who lives half an hour away from me. She came to see me twice, and drove from another city to see me. (Although not far, only 30 minutes, but still shows investment.)

So, both of our dates have been great. I get texts afterwards saying things like "I had a really great time" and then she'd try to schedule another date. We're going on our third one on Wednesday. She hasn't flaked yet, actually she shows up early a lot.

The only problem is, I find her really difficult to read. Normally, I go for the kiss on a first date but this girl seems really reserved. I've never been rejected when going for the kiss on a girl, but for herl I didn't want to do it. She seems extremely inexperienced and she kind of makes ME uncomfortable to go for it, but she's so bangable so I'm going to slow game this one, and I have lots of confidence that I'll be successful.

The thing is, I'm planning on going for the kiss on our next date, but she's really awkward so I feel like she'll play it off like "oh.. umm.." and kind of kill the mood, so how would I go for it in a way that she's prepared? I wouldn't ask "Hey, can I kiss you?" but I want to do it in a strategic way that makes her comfortable and not make me look like a "player."

What would you guys do? I was thinking about steering the conversation to the topic of kissing (I steer it sexually occasionally and she responds pretty confidently surprisingly. She still feels bad that she had sex with one guy that she didn't know very well, and I told her that I only have sex with girls I have a connection with, and throughout the date, occasionally I'd mention that she's cool and that it's nice we have some form of connection.)

So yeah, this girl is puzzling me. I've never really tried with a girl who is so reserved. What would you guys do to open her up to the idea?