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Daddy-Long-Legs, written in 1912 and set at about the same time, is Jean Webster's best-known novel (not to be confused with the webcomic of the same name).

Jerusha "Judy" Abbott is an orphan, having been raised in the unpleasant John Grier Home, which is run by a board of trustees. One of the trustees, whose name is unknown to her except through the pseudonym of 'John Smith,' is impressed by a humorous essay she writes and volunteers to send her to college to study writing. The only condition he places on the generous gift is that she write him regular letters to inform him of her progress, her activities, and her plans. Outside of the first chapter, which sets up the story, these letters form the entire novel. Judy catches one glimpse of her anonymous benefactor from behind, and her only impression of him is that he is very tall and thin; she therefore dubs him Daddy-Long-Legs, and begins to affectionately view him as the father she's never had.

"Daddy" and the reader follow Judy through four years of school and join her as she meets new people — friendly Sallie McBride, Sallie's good-natured brother Jimmie, snobbish Julia Pendleton, and Julia's handsome young uncle Jervis. She spends her summers on a charming farm, tries very hard to become a writer, and falls in love.

The book has received a film adaptation, though it was modified to the point where it almost qualifies for In Name Only (among other things, Judy's name is inexplicably changed to Julie). It was adapted into an installment of World Masterpiece Theater, My Daddy Long Legs (Watashi no Ashinaga Ojisan), in 1990.

The less-well-known sequel is Dear Enemy, published a few years later, in which Judy convinces her old college friend Sallie to take the helm of the John Grier Home and turn it into a warmer and kinder place. Sallie, reluctant at first, becomes very invested in the lives of the orphans, but frequently finds herself butting heads with the eponymous 'Enemy,' her nickname for the asylum's staff physician, Dr. Robin MacRae.

This novel and its sequel contain examples of:

  • The Alcoholic: Tommy, in the sequel.
  • Anguished Declaration of Love: Judy makes one of these, sort of, when explaining to Daddy about her feelings for the man she loves. She just doesn't realize they're the same person.
  • Animated Adaptation: In 1990, as a part of the World Masterpiece Theater. It had none other than Mitsuko Horie as Judy.
  • Anonymous Benefactor: Daddy
  • Babies Ever After: It's noted in the sequel that Judy and Jervis are the parents of a little girl, whom Sallie refers to as "Judy Junior."
  • Black Sheep: Julia's remarks about her uncle Jervis indicate that he is this to the rest of the Pendletons, as he's far less snobbish and much more genial.
  • Bratty Half-Pint: Sadie Kate, in the sequel, although in spite of her antics she's Sallie's favorite kid. Punch is more of a direct example, though he does reform.
  • Bunny Ears Lawyer: Jervis Pendleton
  • The Casanova: Jervis again
  • Captain Ersatz: In the sequel, the doctor's situation with his wife makes him appear to be a more humane version of Rochester from Jane Eyre.
  • Chekhov's Gunman: In the sequel. Sterry, the original farmer at the John Grier Home, is let go from his position after arguing with Sallie. Later he returns and tries to get his job back, to no avail. He breaks into one of the buildings to sleep at night, and accidentally leaves a candle burning...the result being that the entire orphanage burns down.
  • Deliberately Cute Child: Several orphans in the sequel, little Allegra in particular.
  • Determinator: Dr. MacRae is just as stubborn as Plucky Girl Sallie is, which works very well when they're in agreement but just as often leads to them arguing.
  • Embarrassing First Name: Judy hates her real first name, Jerusha, and mentions in one letter that the matron of the John Grier Home got it from a tombstone when trying to name the abandoned infant. When she gets to college, she goes by Judy.
  • Epistolary Novel: In the original, almost the entire story is told through Judy's letters to her benefactor.
    • The sequel cranks this Up to Eleven by being completely epistolary, without the narrative opening chapter of the original, and by being almost three times as long. It's made up of Sallie's letters to Judy, to the 'Enemy', and to Gordon Hallock, her sweetheart in Washington, D.C.
  • Executive Meddling: Sallie suffers this from one of the John Grier Home trustees, "Hon. Cy," as she calls him. She learns to distract him by getting his opinion on things that don't matter, and he does prove very useful to her in his own way.
  • Fiery Redhead: Sallie, though this is made more apparent in the sequel than in the original novel.
  • Funetik Aksent: In the sequel, and not unreasonably. Sallie is of Irish descent, and the doctor is of Scottish, so she tells Judy that sometimes they speak to each other in their ancestral accents. She even writes a few sentences out phonetically so Judy (and the reader) can see what she means.
  • The Ghost: Daddy, who is never seen (or so the reader thinks) until Judy's very last letter.
  • Girl Next Door: Sallie McBride, as well as Judy herself.
  • Gorgeous Period Dress: Daddy very generously supplies Judy with money to purchase new clothes, and she gushes at length about her beautiful dresses.
  • Green-Eyed Monster: Judy doesn't understand why Daddy is set against her spending one of her school holidays with the McBride family. Later, when the reader knows that "Daddy" is really Jervis Pendleton, his motives become clear — he was in love with Judy and jealous of her relationship with Jimmie McBride.
    • Gordon, in the sequel, is insanely jealous of the doctor. Not without reason, as it turns out.
  • Happily Adopted: A few of the orphans in the sequel, especially after the fire.
  • Happily Ever After: The last letter of each book more or less sets this up for that book's respective heroine; the sequel confirms Judy's Happily Ever After status.
  • Heartwarming Orphan: Baby Allegra, in the sequel, who charms everyone — even crotchety, un-charmable Dr. MacRae.
  • Hollywood Fire: In the sequel. The orphanage goes up in smoke, but thanks to their previously-instituted policy of fire drills, all the kids make it out safely. Though Dr. Mc-Rae is severely injured while trying to save Allegra.
  • Ill Girl: Judy falls quite ill during her first year of school, prompting "Daddy" to send her pink roses.
    • Ill Boy: Daddy a.k.a. Jervis almost catches his death of pneumonia toward the end of the story.
  • Innocent Inaccurate: Judy doesn't know anything about Daddy, who prefers to communicate through a representative. This frustrates her, especially when his motives for a decision are unclear. Likewise in the sequel, with Sallie and the doctor; his actions at some points are a complete mystery to her, because she doesn't know he's trying to deny his love for her.
  • It Was a Gift: As the first letter of the sequel clarifies, Judy was basically given the John Grier Home as a Christmas present by her husband Jervis, who is now the chief trustee.
  • Lit Fic
  • Loads and Loads of Characters: In the sequel, oh yes.
  • Long-Distance Relationship: Sallie's relationship with Gordon in the sequel is very much this.
  • Love Before First Sight: The original turns this trope on its head.
  • Most Writers Are Writers: By the end of the original novel, Judy has published her first real story.
  • Mr. Smith: Daddy-Long-Legs instructs Judy to address her letter to "Mr. John Smith". She dislikes such a bland pseudonym so comes up with the nickname "Daddy-Long-Legs". His real name is eventually revealed to be Jervis Pendleton.
  • Mysterious Past: Dr. MacRae won't talk about his, but eventually Sallie learns from his housekeeper that he has a wife and daughter. The wife is institutionalized for being insane, and the daughter, who shows tendencies of the same kind, lives with her grandmother and a devoted nurse.
  • The Nicknamer: Sallie is this for Dr. MacRae, calling him not only "Dear Enemy," but also "Sandy" (a reference to his hair color) and, at least once, "Robin lad." A few others crop up irregularly too.
  • Non-Human Sidekick: In the sequel, Sallie's beloved Chow-Chow, Singapore.
  • Orphanage of Fear: The John Grier Home is a borderline example. The kids did have what they needed to live somewhat comfortably and weren't directly abused, but they still were emotionally neglected.
  • Orphan's Ordeal: Naturally.
  • Plucky Girl: Judy and Sallie (once she settles into her position as orphanage superintendent.)
  • Possession Sue: In-Universe example; at one point after reading Hamlet Judy writes about how she imagines herself as Ophelia, except she's a "sensible" Ophelia who coddles Hamlet until he's cured of his melancholy and they rule Denmark together happily and well after the king and queen die in an accident at sea.
  • Rescue Romance: Done with a twist in the sequel. Sallie explains, in the final letter of the book, that what made her realize she was in love with the doctor was when he risked his life to save Allegra from the fire, and they didn't know if he would survive.
  • Rich Bitch: Julia, although she warms up enough that Judy grows to like her better.
  • Romantic False Lead: Jimmie McBride, whom Judy likes, but only as a friend. Daddy and Jervis don't realize that it's strictly platonic.
  • Scholarship Student: Not precisely, but Judy might as well be this.
    • She does earn an actual scholarship during the course of the first novel.
  • Single Woman Seeks Good Man: Refreshingly averted, especially for the time period. Judy does fall in love, but her main ambition is to fulfill what she sees as her obligation to her beloved benefactor and become a real writer. This is so much her ambition that when the man she loves proposes, she turns him down! And then, she finds out that they're the same person, so it all works out.
    • In the sequel, Sallie breaks off her engagement to Gordon rather than give up the John Grier Home.
  • Slap Slap Kiss: In the sequel, Sallie and the doctor, eventually.
  • Spurned Into Suicide: Almost. After Judy rejects his marriage proposal, Jervis — thinking that she doesn't love him — goes hunting in Canada and nearly dies as a result. He wasn't deliberately trying to kill himself, but he's so depressed that he has a very difficult time recovering.
  • Suddenly-Suitable Suitor: Of a sort, in the sequel. Dr. MacRae has been in love with Sallie for months, but will not allow himself to show it because of his previous tie to his wife. Her death sets him free of that obligation, but by that point, Sallie is set to marry Gordon Hallock. Once she breaks off the engagement, however... (Though to be fair, he didn't tell her right off the bat. His housekeeper could have done so, but she didn't do it either.)
  • Tsundere : Sallie, to Gordon and to Robin.
  • Uncle Pennybags: Jervis, to Julia.