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Will_Newsome comments on Is Rationality Maximization of Expected Value? - Less Wrong
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Even if you're optimizing for enjoyment and satisfaction and fun, gambling isn't necessarily a great way to do that. Another good question to ask subjects who answer "yes" to questions A and B would be "How much money would you be willing to lose at the casino before that starts to outweigh your enjoyment of the experience?" or "How much money would you be willing to lose at the casino before you'd regret not choosing something that is (in your estimation) a more cost-effective route to the same amount of enjoyment?"
Taking into account my other comment, I think that perhaps it'd be best to ask the less informative but much simpler question "How much money have you set aside for gambling today?" before the other two questions.