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If you’re familiar with the original film, you might feel a disconnection between the silliness of Halloween Town and some of the solemnity of this story. Compare the tone of the movie to that of the story. How are they similar or different?
Does Sally come across as a strong character at the story's beginning? What are her strengths and weaknesses? How does she change in the course of the story?
What do you think of Jack and Sally’s relationship? Does he support her as much as he should?
The story is supposedly aimed at a young adult audience. Compare it to another young adult novel that might have similar themes (for example, Twilight by Stephanie Meyer).
Choose a popular fairy tale (or several) and compare it to Long Live the Pumpkin Queen. What features or incidents do they have in common? Alternatively, compare the story to Stephen Sondheim’s musical Into the Woods.
Some readers mention that Sally doesn’t seem to confront any great danger. Do you feel that the story offers a conflict that feels significant? What is the conflict?
Does the story seem primarily written for a female audience? What do you think male readers might learn from it that they wouldn’t learn from a book with a male protagonist? Alternatively, how do you think the story might have been different if the protagonist had been a young man?
In The Nightmare Before Christmas, it was strongly implied that Doctor Finkelstein created Sally. Long Live the Pumpkin Queen gives her an entirely different backstory. What do you think of the change? Do you think it is justified? Does it add to your enjoyment of the story or detract from it? Why?
Halloween Town is a strange and arguably disturbing place. What do you think it would be like to live there? What about the other holiday worlds?