Jerusha "Judy" Abbott is a Canadian orphan, who at 17 is still living in the orphanage, mainly because they are using her as free help. She is frequently told that she needs to keep her strong opinions and overactive imagination to herself, or nothing will come of her. She dreams of becoming a famous author and when a wealthy benefactor of the orphanage offers to send her to college on a scholarship, she is closer to achieving said dream. She doesn't know who he is, having only seen his shadow as he left the matron's office, but she knows that he is tall, and his shadow resembled a daddy long-legs. Hence, when she is told that she needs to write letters to her benefactor detailing her progress, she addresses each one to "Dear Daddy Long-Legs".
Having never had a family of her own, Judy (as she reinvents herself at college. Who can blame her for wanting to be rid of the name Jerusha?) starts imagining that Daddy Long-Legs all the relatives she's been missing. Going to college and receiving an education, Judy thrives. She loves learning, she loves improving her writing and making new friends. She never gets any replies to her letters, but the occasional gift (sometimes quite extravagant) proves that her anonymous rich benefactor reads her missives and doesn't want her to feel left out among the other girls at the college. Very occasionally, Judy will get written instructions through her benefactor's secretary, who among other things, helps find her places to spend her summers, while the other girls go home to their families.
As she grows older and her education is coming to an end, Judy becomes more and more curious about the identity of "Daddy Long-Legs" and tries to use her prodigious imagination to figure out who he might be.
I picked up this book both because Dear Mr. Knightley, which I really liked, was inspired by it (which meant that I wasn't really surprised by any of the major story beats, as they are pretty much the same) and because Forever YoungAdult and the Book Smugglers, both review sites I trust and often agree with, rated it 5 stars and called it a must-read classic. Written in 1912, I'm sure this is a beloved book to many, but whether it's because I'd just read modern book with a very similar plot, or whether I just found some aspects of the book a bit disturbing, it just didn't entirely work for me.
While Judy is rather delightful, smart, opinionated and a bit too prone to speaking (or writing) her mind before she thinks about what she's actually saying, there was something very off-putting to me about her addressing most of her letters to "Dear Daddy". Especially as based on the reviews I'd seen, I knew that there was a romantic subplot, and it was clear that she was actually going to fall in love with her benefactor, without knowing who he really was. When "Daddy" starts dictating where she spend her free time, obviously to prevent her from spending more time with her college friend's brother, it left a bad taste in my mouth. The reviewer on Forever YoungAdult points out that Judy frequently disregards the attempts at manipulations from her benefactor, and once she wins a scholarship due to her writing skill, she insists on being allowed to start paying back the money she's been given so far, not wanting to be in debt for any longer than necessary.
I don't think it was just because of just having read Dear Mr. Knightley that I figured out quickly who "Daddy Long-Legs" was. While the character seems perfectly pleasant, and has very socialist leanings for a rich person of the time, I just couldn't get over the inappropriate way he keeps trying to direct Judy's life. Judy herself, as I have already mentioned, is great. She, like the precocious orphan girl ever, Ms Anne Shirley is the reason I liked the book as much as I did. It's really not going to be a book I revisit though, and the hero, if he can be called that, did little but skeeve me out.