If you're depending on a particular reaction in order to carry on any sort of conversation, you'll probably not have a very good one. The other person is very unlikely to follow your script, whatever it may be... that's the reason that the Turing Test works so well. Computers follow scripts in conversation, people don't.
A conversation is a kind of dance. One moves, the other reacts and plays off of it, then the first one plays off of her reaction and so on. You can't really plan it all out beforehand... you've got to get your right brain firing on all cylinders and verbally dance with her.
The more practice you get, and the less anxiety and distraction you've got clouding your brain, the better you become at it. And if you're bringing a hidden agenda (as in, what should I say now to make her smile/want me/do me/love me), that's not conducive to getting her to let her guard down and dance with you.
And it could be that she's just determined not to work with you, and there's nothing you can do about it. Then what?
a fine and enviable madness, this delusion that all questions have answers, and nothing is beyond the reach of a strong left arm.