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Why are you guys talking about escalation? That's not even what the OP's question is about. Yes, escalate if you can, but that's besides the point here.
You should be happy she is playing the guessing game. It's a form of push/pull. She is creating a subtext within the conversation to allow you two to have fun and for you to demonstrate value and give some witty funny answers.
I met this HB9 today and asked what ethnic background she was, and she told me to guess. Ok, I'd never get it in a million years because she didn't look like what she was. However, if she just said "Mexican", then the entire conversation might have died right then and there. When she says guess, I interpret that as she wants to talk to me and has given me the greenlight to be funny and have some liberties. It's a good thing. Play it up.
Yo, thanks for the informative response! Appreciate it! And yeah, I figured that the whole concept of guessing seems to be a really good one because we had a guessing game on the first date and it was insane...