Pip is an orphan living on the Kent marshes with his abusive sister and her husband, Joe Gargery, the village blacksmith. While exploring in the churchyard near the tombstones of his parents, Pip is accosted by an escaped convict. The convict scares Pip into stealing food for him, as well as a metal file to saw off the convict's leg iron. Returning with these the next morning, Pip discovers a second escaped convict, an enemy of the first one. Shortly afterward, both convicts are recaptured while fighting each other.
Pip's pompous Uncle Pumblechook arranges for Pip to go to the house of a wealthy reclusive woman, Miss Havisham, to play with her adopted daughter, Estella. The house is a strange nightmare-world. Miss Havisham's fiancé jilted her on her wedding day and she still wears her old wedding gown, although she's now elderly and wheel-chair-bound. The house has been left as it was on her wedding day and even the old wedding cake is still on the table. Estella is beautiful but haughty and tells Pip that he is coarse and common. Pip is immediately attracted to Estella in spite of how she and Miss Havisham treat him. Although the visits are emotionally painful and demeaning, Pip continues to go there for several months to play with Estella and to wheel Miss Havisham around. He also meets her toady relatives who want her money and hate Pip. Pip does earn a kiss from Estella when he beats one of the relatives, the Pale Young Gentleman, in a fistfight. Pip tries to better himself to win Estella's admiration by working harder with his friend, Biddy, at night school. Biddy's grandmother runs the night school.
After a number of months, Miss Havisham pays for Pip's blacksmithing apprenticeship with Joe. Pip had looked forward to that for years, but now that he has seen "genteel" life, he views the forge as a death sentence. However, he hides his feelings from Joe and performs his duties. During this time, he encounters a strange man at the Jolly Bargemen, a local pub. The man has the file that Pip stole for the convict years before. The man gives Pip two one-pound notes. Pip continues to visit Miss Havisham on his birthday and on one of these occasions, his leaving work early instigates a fistfight between Joe and Joe's assistant, Dolge Orlick. Orlick resents Pip and hates Pip's abusive sister. On his way home from that visit, Pip finds out his sister was almost murdered and is now mentally crippled. Biddy comes to live with them to help out. Pip is attracted to her even though she is not educated and polished like Estella.
One evening, a powerful London lawyer, Mr. Jaggers, visits Pip and Joe and informs them that Pip has "great expectations." Pip is overjoyed and assumes the windfall is from Miss Havisham, who wants to prepare him for Estella. He gets a new suit of clothes and is amazed at how differently he is treated by Mr. Trabb, the tailor, and by Uncle Pumblechook. When Pip gets Trabb's shop boy in trouble for not treating Pip with respect, he realizes how money changes things. He has a conversation with Biddy and asks her to work on "improving" Joe. Pip accuses her of being jealous of him when she suggests Joe does not need improving. By the end of the week, Pip is on his way to London to become a gentleman.
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