Yes. You might look at some of the social skills curricula written for people with autism-- I think this might be addressed in some of Michelle Garcia Winner's materials, or in a new Australian curriculum called "Secret Agent Society." He needs to learn (and practice) how to look at his listener for cues of interest/disinterest, so that when he's starting to go into a big lecture, and the listener gets bored, he knows and will stop. Then he can make the choice to make real, interactive conversation instead.

Of course, it's likely that the "garden path" is so pleasant for him that he'd like to go to all the stops on it-- that makes this behavior harder to change, because it tends to happen with topics that are inherently rewarding to think about.

Any chance of finding a SLP to work on these skills? It should really be their bailiwick, although finding one who knows how to teach this stuff is hard.

DeeDee