The only conversation option with the Fairman is regarding the robot. Nothing about the shooting gallery game. I've been following a walk-though and I seem to have done everything up to the point of starting the shooting, but he won't talk about it. I even switched the robot oil with the adulterated oil. I guess I'm stuck here...
UPDATE: I needed to have a dollar in order to get the conversation about the shooting game. I found one in the upstairs of the saloon. Now I can continue.