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Estella is generally viewed as a mean and heartless character, which is what she was raised to be. She was cruel to him, as she was to all men. Though, according to Lucille P. Shores, Pip fails to realize that Estella really shows her affection for him in her own way. Pip is subject to her constant mockery and insults, and yet when he fights over her with Herbert she rewards him with a kiss. Estella knows all too well that she has been warped by the demented Miss Havisham, this is why she warns him away from her. She has strong feelings for him, maybe not of love but certainly of admiration, and that is why she cannot subject him to her grating personality. Shores submits that Estella "knows that she cannot make Pip happy, and she has too much affection for him to link her unhappy life with his", she refuses to ruin his life by her presence. Therefore her rejection of him is possibly her greatest gift to him, at least in her own eyes. When Pip sees hatred and scorn, Estella is really trying to show her admiration and fondness of him. When Estella and Pip first meet as adults, Estella looks at Pip, looks at her shoe, and then back to Pip and laughs. Shores states that at this point Dickens perfectly captures a woman's subconscious feelings toward a man she feels attracted to, and yet to the naïve Pip it is just more rejection from Estella. Shores, Lucille P. "'The Character of Estella in Great Expectations." Massachusetts Studies in English (Fall 1972): 91-99. Rpt. in Novels for Students. Ed. Marie Rose Napierkowski. Vol. 4. Detroit: Gale, 1998. Literature Resource Center. Web. 23 Jan. 2011.

From a young age, Pip went to the Satis House and played cards with Estella. That's where he fell for her and where his desire for nobility began. Parkinson submits that while games are typically played for enjoyment, Pip did not enjoy playing cards, or his life as a gentleman. Pip's approach to his life as a nobleman is similar to his approach to cards. He does neither for enjoyment, he does both to impress Estella, and in the end fails to do either. Pip's wealth brings him no happiness, only discomfort and debt. Parkinson suggests that economic standing is determined by chance in addition to skill, which is accurate in Great Expectations, Pip and Estella get rich through luck, while Magwitch gets rich through mostly hard work and only a little help from luck. In addition, Pip loses at every game, no matter how hard he tries, and he blows through his fortune and ultimately loses it all. Life is just one big game, and playing for the wrong reasons can leave you destitute.