hah I love this game.
Sometimes it gets amazing results.
I cant count how many times Ive done it. Ive gotten so good in it has started to backfire. Ive failed twice. Once when I had just learned it and once when I won 16 (yes sixteen) drinks from this chick

.. I just wanted to see how many times I can do it. We took double or nothing and I won 4 times in a row. She said I made her feel stupid, bought me a drink and left.. crap..
I usually start with 2 some of the easiest questions ever. Always something random and I try to hide a neg there if I can. Third question is "what colour is not on a rainbow".. since theyve had 2 easy questions in a row and they expect a third one they usually fall for this saying something like "black". Its unbelievable how usually they fall for the rainbow question. If they figure it out then just continue with "how many questions were there again" etc. and you need to be say it with a by-the-way -mood. as if u stopped playing.
One interesting point ive noticed is that if you ask "what colour are my boxers" .. like 90% will answer "pink" .. ive been thinking about getting pink boxers because of this.
You can also use any sort of distractions to your advantage. For example if her friend comes busting in etc. start a conversation with her and later snipe a question to your target when she is distracted.