P.S. If you’ve already read the book, feel free to add any other discussion questions of your own in the comments!
From Anne Shirley to the Boxcar Children, precocious orphans are a common trope in children’s and young adult literature. Growing up, did you have a literary orphan kindred spirit? What attracted you to that character?
1. Most readers of Daddy-Long-Legs fall in love with Judy, despite the fact that she can be pushy, manipulative, and judgmental (as well as consistently lying by omission about her upbringing). What makes her such an infectiously likable character? And if anyone in your book club did not like Judy, why not?
2. On a scale of 1 to 10, how creepy did you find the romance in this book, and did that detract from your enjoyment of the story?
3. Anne of Green Gables was published in 1908, and Daddy-Long-Legs in 1912, both to immense popularity (Indeed, Jean Webster was such a well-liked author that Theodore Roosevelt invited himself on her honeymoon. Like you do). Yet, the former remains a classic of children’s literature, while the latter has been, at least comparatively, long forgotten. Do you think that Daddy-Long-Legs deserves the same kind of lasting popularity as the Anne books, and if so, why have so few people read it?
4. There is a great deal of social commentary in Daddy-Long-Legs. How do you think some of the more socialist, feminist themes would have been perceived when it was published? How do some of these themes still resonate today, 100 years later?
5. There have been several film/television adaptations of Daddy-Long-Legs over the years, most of them INSANE. Do you think it’s possible to translate this book–and epistolary novels in general–to different media formats, while preserving the spirit of the original? How would you like to see this novel adapted, if at all?