Pip and Estella are linked, not just by the plot, but thematically as well. Both Pip and Estella are defined by their “expectations,” although what whose expectations are, and the degree to which they are fulfilled, varies quite a bit.
Pip meets Estella at Miss Havisham‘s house. Estella, also an orphan, is being raised by Miss Havisham to “break hearts.” Estella is critical of Pip’s working class ways; for his part, Pip finds Estella proud, pretty, and insulting. Estella is a mystery to Pip; even though he desires her, her aloofness confounds him, and he also understands that she is toying with him. When after a visit on Miss Havisham’s birthday Estella permits Pip to kiss her cheek, Pip feels that “the kiss was given to the coarse common boy as a piece of money might have been, and that it was worth nothing” (chapter 9).
The value of affection, and the difference between genuine feeling and manipulation or double-dealing, is an important theme in the book. Pip’s realization later in the book that he “adores” Estella is a case in point. Pip, keenly aware that “fortune” (Miss Havisham?) has raised him up, thinks that perhaps Miss Havisham has groomed him to be Estella’s husband. The fact that his is not the case—that not only is Miss Havisham not Pip’s mysterious benefactor, but Estella is purposefully attempting to “deceive and entrap” Drummle, and does eventually marry him. It is no surprise that her marriage with Drummle, based on cynicism and contempt, becomes abusive. But Estella’s marriage becomes an important lesson for both Pip and Estella: Estella learns the value of genuine affection, and Pip learns that his “luck” or destiny is not subject to his whims. Even in Dickens, the story does not always turn out the way it ought.
There is some ambiguity about whether Pip and Estella marry after Drummle’s death. The sense, however, is that they do stay together in some way, and that the bond they share, though both understand it differently, cannot be broken.
Pip meets Estella when he goes to work for Miss Havisham. He is stunned by Estella’s beauty, but she looks down upon him. Estella does not see Pip as anything but a struggling lowlife and treats him with scorn.
Although the reader might be tempted to completely blame Estella for her attitude and behavior, it is important to recognize Miss Havisham’s role in instilling those values in her. Pip falls in love with Estella, but the lady is unable to reciprocate his feelings.
Pip believes that if he becomes a gentleman, his fortunes will change, and when the opportunity presents itself he gladly takes it and moves to London for his training. He later goes back home and visits Miss Havisham and Estella. He is informed that Estella would be coming to London, and he is expected to be her escort. The arrangements lead him to think that he was being groomed for Estella. However, Pip discovers that Estella is going to get married to Drummle, and despite his objections, Estella goes ahead and gets married.
She suffers through an abusive marriage, and she admits that it changed her. Pip and Estella meet again, but she is widowed, and a popular ending suggests they stayed together. These changes provide valuable lessons to both characters as they learn the value of being humble.
https://www.owleyes.org/text/great-expectations/read/chapter-i
Pip’s relationship with Estella begins as playmates, arranged by Miss Havisham. Pip learns eventually that Miss Havisham’s plan is to train Estella to break men’s hearts as a means of revenge for her own broken engagement on the day of her wedding. Estella treats Pip cruelly, making fun of him for his working class ways. Yet Pip falls in love with her, despite the hurt he feels.
When they have grown up and Pip goes to live in London and become a gentleman, Estella treats him more kindly but only as a friend. Pip sees her as his ideal, but she is more interested in finding a gentleman, which she cannot accept that Pip is becoming. It is possible that, since the two of them have now become friends, Estella does not want to break his heart, despite Miss Havisham’s intentions.
After Pip finds that Miss Havisham is not his benefactor, nor did she ever intend for him to be Estella’s husband, Pip and Estella move apart. Pip no longer feels that he can be the type of gentleman that Estella desires, and Estella marries Bentley Drummle. After several years, Estella and Pip meet. Estella’s marriage, which had been abusive, is ended with Drummle’s death. This gives a hint of a promise that Estella and Pip will get together, accepting each other for what the other is, perhaps with a happy ending.
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