He doesn't necessarily learn anything regarding the Restricted Section in his conversation with Harry; however, immediately after his conversation is probably his best chance to have McGonagall listen to him about the Restricted Section.
Dumbledore and McGonagall don't really have very many options to cheer Harry up. It's suggested that they already tried other students. Regarding friends, his closest would be McGonagall and Quirrell, neither of whom worked, Hermione and Draco, who are both inaccessible for obvious reasons, and his parents. Of all of these, the last seem like the best option. This is particularly so considering that Harry would very likely want to shield his parents from his present emotions in a way that is not true of Dumbledore and McGonagall. We can debate how well it would work, but short of explicitly using magic on Harry (which might not even be possible, now that he's an Occlumens) it's the only thing McGonagall and Dumbledore could do that would have any kind of chance of success.
This is a new thread to discuss Eliezer Yudkowsky’s Harry Potter and the Methods of Rationality and anything related to it. This thread is intended for discussing chapter 90. The previous thread has passed 750 comments.
There is now a site dedicated to the story at hpmor.com, which is now the place to go to find the authors notes and all sorts of other goodies. AdeleneDawner has kept an archive of Author’s Notes. (This goes up to the notes for chapter 76, and is now not updating. The authors notes from chapter 77 onwards are on hpmor.com.)
The first 5 discussion threads are on the main page under the harry_potter tag. Threads 6 and on (including this one) are in the discussion section using its separate tag system. Also: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17,18,19.
Spoiler Warning: this thread is full of spoilers. With few exceptions, spoilers for MOR and canon are fair game to post, without warning or rot13. More specifically: