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.