Daddy Long-Legs is the story of a young orphaned woman, Judy Abbot. The book is written by Alice Jane Chandler Webster, who wrote under the pseudonym Jean Webster. She was born into a literary family and was Mark Twain’s niece. Webster began writing at a young age. Her works include several books for children such as Four-Pools Mystery, Much Ado About Peter, Dear Enemy, When Patty Went To College and Just Patty.
Jerusha Abbot a.k.a. Judy is brought up in the John Grier Home, where orphans are brought up on the charity of trustees and donors. Forced to go through high school wearing other girls’ cast-offs, Judy often dreams of what life might be like in an ordinary household with a real family. But her future seems bleak as she dreads she will spend her life in the care of the children in the orphanage. Fate intervenes when a generous trustee expresses his desire to fund her college education. All he asks in return is that she work towards being a writer. While he asks for regular bulletins reporting her progress, she receives all this information through the matron, Mrs. Lippett, who also tells her not to expect any reply. The trustee wishes to remain completely anonymous and asks for the letters to be addressed to Mr. John Smith.
After a short narrative in third person, the rest of the novel consists of letters written by Judy. Having only distantly glimpsed him once, she christens her benefactor Daddy Long-Legs, a reference to his immense height. The letters follow Judy through her (mis)adventures, attempts at fitting in with the crowd and her new-found independence. Her friendships blossom, particularly with Sally McBride, a sweet-tempered girl from a large family, and Julia Pendleton, a self-assured young woman of aristocratic lineage. Her college years are peppered with basketball games, reading fascinating books, last minute study sessions and spontaneous outings with her fellow students. Besides spending some vacations with Sally’s family, she also spends a large part of her summers at Lock Willow Farm which is run by the Semples, an elderly couple. She also spends a summer tutoring the young daughters of a lady named Mrs. Paterson
For the first time in her life, she learns to interact socially with men, such as Sally’s brother Jimmie and Julia’s young, handsome uncle Jervis. Jervis also spends part of the summer at Lock Willow, as Mrs. Semple had once been his nanny. While Jimmie often escorts Judy to dances at her own college and Princeton, where he studies, she spends a lot of time with Jervis too, who is often critical of her writing yet offers his inputs to help her improve. Eventually, Jervis Pendleton makes a proposal of marriage to her, which she turns down. She feels that the fact that she is an orphan raised in a charitable institution makes her unfit to be his wife, while he believes she has turned him down for another suitor. For all four years, every detail of her daily life is intimately described in her letters to her elusive guardian, before she is finally invited to meet him. Much to her surprise, her guardian turns out to be none other than Jervis Pendleton! The book has what might best be described as a fairytale ending, for not only does she get engaged to Jervis, her book also gets published.