Ask questions to which any conceivable answer can be construed as wrong; the triumvirate of sex, politics, and religion will work well here. Also, ask questions about his work or education, and when he answers honestly, accuse him of trying to impress you. (By the way, this is the one exception to the gay male taboo against discussing work or education, so make it count.) If it's a dinner date, take exception to the food that he orders, and accuse him of being either too bossy or not bossy enough to the waitstaff. Nothing cuts the ice like constantly putting him on the defensive.
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