I bet you're way too boring and logical. If this seems like you, then:
Are you testing her boundaries? Playing with her head a little bit and testing her reactions? Think about it like this...If you want to know how someone really is, you need to play them and create a scenario that elicits a response. Maybe you say something like, "sorry, I'm a little dazed right now, I just smoked a lot of crack before I got here." That should get a response her, right? Then you can qualify her based on her response. If she's uptight "I was kidding...I like a gal who can take a joke." Or if she jokes back, you can banter back jokingly or "hah I'm glad you have a sense of humor..The last girl I went on a date with was so boring."
This type of shit is about communicating with emotions. It's all about evoking responses and having fun. When you're asking questions constantly, you're making someone feel judged and bored cause there's no fun emotion behind it. You gotta loosen up, have fun and let go of trying to look good or trying to impress her.