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I guess I would be inclined to ask to kiss to my girl friend just cause I would want to respect her boundaries and don't want her to think I was creepy. She seems to be very very cautious about going to real life from the internet and probably would think I was being a gentleman by doing so. Or is it better to keep the first date very very casual and wait a few dates to kiss her? Would you think that is weird and the guy is not assertive enough and showing enough interest?

Or should I just ask her these questions myself and communicate and say I know you are cautious and I'm trying to be respectful, but I really like you and I want to know what you are comfortable, etc.