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Offer to sell him a fine leather jacket
"I'm," you say, "selling these fine leather jackets!"
"Hmmm..." replies Guybrush, "That's a good line! You mind if I use it?"
"Sure," you enunciate, "Just don't use it on humorless bounty hunters. Or the Mafia."
"I don't think that's going to be a problem!"
GAME OVER