I've included a selection of questions from The Valley Cottage Library's "The Haunting of Hill House discussion guide". You don't need to read any of them and you can discuss whatever interests you. They are only here to give you ideas on what to write. I can't wait to hear from you!
Discuss the reasons Dr. Montague chose Eleanor, Theodora,
and Luke to stay in Hill House. The psychic phenomenon which they experienced
does not seem to have made a great impact on them. How is this significant?
Eleanor often tells herself that she deserves her newfound happiness at Hill House. What is the cause of this happiness? Is it real or an illusion? How do her feelings about both the house and its temporary inhabitants change over the course of her stay?
How does Jackson establish a romantic triangle, given the social proprieties of the era in which the novel is set? (It was first published in 1959.) What is the significance of the song refrain Eleanor keeps repeating, “journeys end in lovers meeting”?
Do you believe Eleanor was justified in feeling resentful towards the others for treating her like a hysterical female? Or do you believe the others in the party saw something in Eleanor that alarmed them?
Did Eleanor intentionally let her mother die, or is she merely suffering from bereavement and a mistaken feeling guilt?
Discuss the differences in the methods Dr. and Mrs. Montague use to study the paranormal. Which approach, if any, do you believe is most successful? Why?
Why does Mrs. Montague believe that a loving attitude is more effective in a haunted house than a fearful one?
The planchette is similar to the ouija board; it is a method
of communicating with spirits from beyond through the process of automatic
writing. What do you make of the planchette’s messages to Eleanor?
While The Haunting of Hill House is told in the third person, by an omniscient narrator, the point of view throughout the novel is almost exclusively Eleanor's. Is her viewpoint reliable?
It seems clear that we are meant to believe the reality of the physical manifestations of Hill House’s “possession” by otherworldly forces, as many of the phenomena are witnessed by two or more people, whereas many authors would have left the reality of these events ambiguous. What do you make of Jackson’s decision?
Do you see Hill House's horrors as being different for its male and female inhabitants? If yes, then what differences did you notice, and how do they suggest the novel's take on gender issues? If no, explain why you don't see any differences, and what this equal-opportunity terror has to say about gender in the novel?
Assume that the ghostly manifestations are the result of Eleanor's blooming telekinetic ability. What does this suggest to you about the character of Eleanor?
Imagine that the events of Hill House took place this year. How would the story, themes, and characters change to become relevant for our brave new(ish) world?
The Big One: what is it about Hill House that allows it to consume Eleanor's sanity so efficiently? Or, what is it about Eleanor that allows Hill House to consumer her sanity?

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