"It is a part of Miss Havisham's plans for me, Pip," said Estella, with a sigh, as if she were tired; "I am to write to her constantly and see her regularly, and report how I go on—I and the jewels—for they're nearly all mine now." (33.58)
Miss Havisham may claim that she never planned to ruin Estella's life, but it sure seems like she tried to. Check out the way Estella and the jewels seems to be one and the same.
Whenever I watched the vessels standing out to sea with their white sails spread, I somehow thought of Miss Havisham and Estella; and whenever the light struck aslant, afar off, upon a cloud or sail or green hill-side or water-line, it was just the same. Miss Havisham and Estella and the strange house and the strange life appeared to have something to do with everything that was picturesque. (15.4)
Okay, we all feel a little dreamy when he look off at the horizon—Pip is just a lot more poetic about it. When he looks out onto the marshes and sees horizon is populated by sails or other things, Pip instantly feels closer to his dreams. His fear? Having nothing on the horizon, and nothing to hope for.
The lady whom I had never seen before, lifted up her eyes and looked archly at me, and then I saw that the eyes were Estella's eyes. But she was so much changed, was so much more beautiful, so much more womanly, in all things winning admiration had made such wonderful advance, that I seemed to have made none. I fancied, as I looked at her, that I slipped hopelessly back into the coarse and common boy again. O the sense of distance and disparity that came upon me, and the inaccessibility that came about her! (29.38)
Is it just us, or does Pip seem a lot more interested in thinking about the distance between himself and his dream than about the dream—i.e., Estella—itself? We get the sense that he wouldn't even know what to do with her if he got her.
She had adopted Estella, she had as good as adopted me, and it could not fail to be her intention to bring us together. She reserved it for me to restore the desolate house, admit the sunshine into the dark rooms, set the clocks a going and the cold hearths a blazing, tear down the cobwebs, destroy the vermin—in short, do all the shining deeds of the young Knight of romance, and marry the Princess. (29.2)
Pip's dreams seem to be made of images, actions, and theatrical elements rather than emotions or substantive encounters. Well, that makes sense—they're dreams. Instead of imagining a real moment of happiness and understanding with Estella, Pip imagines dramatically and magically curing Satis House. It's all very Beauty and the Beast, minus the singing candelabra. (We wish there were a singing candelabra.)
"I am ashamed to say it," I returned, "and yet it's no worse to say it than to think it. You call me a lucky fellow. Of course, I am. I was a blacksmith's boy but yesterday; I am—what shall I say I am—to-day?" (30.26)
Just like today, most of the people in Pip's life derive their identity from the job that they do. Pip wants to be a gentleman who derives his identity from what he is rather than what he does—but he's not there yet. He can still only dream about it.
While my mind was thus engaged, I thought of the beautiful young Estella, proud and refined, coming towards me, and I thought with absolute abhorrence of the contrast between the jail and her. (33.4)
We're not so sure that Estella and the jail have so little in common. They're both associated with death, and they're both locked up tight. One is a dream and one is a nightmare, but other than that—yep, pretty similar.
Miss Havisham's intentions towards me, all a mere dream; Estella not designed for me; I only suffered in Satis House as a convenience, a sting for the greedy relations, a model with a mechanical heart to practise on when no other practice was at hand; those were the first smarts I had. (39.98)
Pip's great expectations just led to suffering—and growing up a little. Dreams may only bring suffering, but only suffering makes you a man.
For an hour or more, I remained too stunned to think; and it was not until I began to think, that I began fully to know how wrecked I was, and how the ship in which I had sailed was gone to pieces. (39.97)
Here we see the connection between those ships that Pip used to watch on the marshes at home those many years ago and his current circumstances. When he watched the ships on the horizon, he'd dream about the life he couldn't have. The ships became a metaphor for a life of money and privilege—but once he actually got on board, it promptly sank. What does he have on his horizon now to dream about?
Too heavily out of sorts to care much at the time whether it were he or no, or after all to touch the breakfast, I washed the weather and the journey from my face and hands, and went out to the memorable old house that it would have been so much the better for me never to have entered, never to have seen. (43.57)
Pip thinks he would be happier if he had never been exposed to Miss Havisham's house, which reminds us that Pip was first made to visit Miss Havisham in order to fulfill or attempt to fulfill the dreams and hopes of others: Mrs. Joe and Mr. Pumblechook (not to mention Miss Havisham).
"It would have been cruel in Miss Havisham, horribly cruel, to practise on the susceptibility of a poor boy, and to torture me through all these years with a vain hope and an idle pursuit, if she had reflected on the gravity of what she did. But I think she did not. I think that in the endurance of her own trial, she forgot mine, Estella." (44.43)
Over and over again, we see hopes and dreams turning people selfish and destructive. But Pip still chooses to believe that humans are innately good, and just derailed by misguided dreams.