This actually comes from Neil Strauss (Style).
The game works like this. You make a simple bet with the person (e.g. a drink). You have to ask them 5 questions and they have to get every question wrong. If they get 5 wrong, they win.
The first three questions really don't matter. Where are we? What's your name? What's your favorite bar?
On the fourth question, stop and look a little perplexed. Then ask "wait, what question are we on?" This will get a good number of people. But if they are too smart follow up with this...
When they are reveling in how they weren't tricked say: "Ok, Ok, you got me. You didn't fall for it. (look skeptical) Have you ever played this game before?"
They will usually answer honestly "no" to show just how smart they are. And then you win, because they answered the fifth question correctly.
The fourth question plays on a person's natural generosity. And the fifth question plays on a person's natural ego.
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