Goodness. Please don't bow out of the conversation, I really appreciate your input, Linda.
Regarding the whole Goblet of Fire thing (when did this become a 'thing'?) - first of all, he read the first three books both on his own and as a read-aloud with his siblings. He's been dying to read Goblet of Fire, but because we're doing a summer reading program with a goal of reading 10 books, I told him to leave it 'til last so he'd make sure he was able to complete the program. So this isn't something I'm making him read. Anyway. My first question was, "So what's going on? Catch me up." That's when he said, "Um, Harry got a smaller slice of grapefruit than Dudley.." He looked overwhelmed by my question, which is typical, so I reminded him that I'm looking for the big plot points (and re-explained what that meant), not little details. My follow up questions were:
"Where is Harry when the book opens?" (he answered, at his aunt's, and he got a letter from Ron about the Quidditch World Cup)
"So he gets to go to the World Cup? Do the Weasleys come to pick Harry up?" - I was trying to lead him to remember the whole blasting apart the fireplace bit, which is funny. He said 'yeah' and when I asked him how they got there, he said, "A car?"
Then I asked, "Did anything funny happen to Dudley while the Weasleys were there?" He remembered that something happened, after some prompting, but was unable to say something like, "Fred and George gave him a sweet that made his tongue grow huge."
As you can see, I'm not asking questions like, "What did Fred say while he was behind the boarded up fireplace?" or "What did Vernon chuck at Arthur's head?" I was asking about the parts I thought he would be most interested in.
Generally, when I ask questions like this, I make it fun and engaging, rather than like a quiz. We giggle and share stories that we both like. I never make him read books that he doesn't want to - everything is his choice. Linda, what you said about him getting lost in the book because he doesn't understand the last five chapters is right on the money. When I don't prompt him frequently with questions, he gets bogged down and can't give me a high level summary of a book. I'd never let him read something as long and complicated as Harry Potter without checking in frequently, but for shorter books when he reads a few chapters in a sitting, I don't want to have to be at him constantly to summarize. Say I asked him for a quick summary of My Side of the Mountain, what I'm looking for is, "A boy runs away to live in the woods. He learns how to make himself a house and get food. He gets a pet falcon and meets a few friends. Then his family comes to join him in the woods." I've explained this to him several times, and given him examples. We've read books together, chapter by chapter, with me modeling what kind of summary I'm looking for.
I guess I just don't know what else to do besides sit with him as he reads and prompt him to sum up every page or so.
Thanks for the input, guys!