Never mind, I'll skip the soup. The difference between these is the cost of the answer. In the first conversation, the guest got the answer immediately. In the second, the delay was too much so they opted to continue without getting the information. We've seen the same phenomena in testing.
Users often avoid help because of the delays associated with it.
They fear that, after a hefty time investment, they won't find anything helpful. We've see promising results with buttons labeled Hints or Tips. These bring up small dialogs, with short explanations, usually in the context of the user's work. Users subconsciously perceive that it won't cost them much to get the information, so they explore these buttons. Once you start watching your users work with your products and documentation, the usability problems will become obvious.