Great Expectations
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The movie begins with young Finnegan "Finn" Bell (Ethan Hawke) exploring the beaches of the Gulf Coast of Florida. An escaped convict (Robert De Niro) suddenly pops out of the water and overpowers him, making Finn promise to bring back food and medicine and a bolt cutter to get the iron shanks off his leg next day. Finn does, and the convict unexpectedly tries to make Finn take him by boat to Mexico. The police seize the small boat heading out to sea. The convict hides on a buoy, and Finn's boat is towed back to shore. The next day, Finn sees on the news that the convict has been caught, and that he was Arthur Lustig, a former mobster and his sentence is the death penalty.

Uncle Joe (Chris Cooper) gets called to Paradiso Perduto ("lost paradise"), home of the richest lady in Florida, Ms. Nora Dinsmoor (Anne Bancroft). Ms Dinsmoor had gone crazy several years before after being left standing at the altar by her fiancee. Ostensibly he was called there for a gardening job, but he does no gardening. Instead, she slips him a large sum of money under the door, calling it "gas money." Meanwhile, Finn, who he brought along, meets young Estella (Gweneth Paltrow) in the overgrown garden. Ms Dinsmoor sees them interacting and calls Maggie (Kim Dickens), Finn's sister, to ask her to let Finn be a playmate for Estella, even though Estella apparently dislikes Finn. Maggie pushes Finn into this for the money.

On Finn's first visit to Ms Dinsmoor, she is disappointed when Finn cannot dance for her, but is intrigued when he says he can draw. She forces Estella to sit for a portrait, which Finn draws with make up on an old piece of wallpaper. While he draws, Ms Dinsmoor warns Finn that he will fall in love with Estella and have his heart broken. After the portrait session, Ms. Dinsmoor calls it a day and asks Estella to help Finn find the door. On the way out, she pauses to take a drink from a water fountain and politely offers him a drink from it as well. While Finn is drinking, Estella, who was playing a trick on him, manages to give him a tongue kiss.

Several years pass. Maggie runs away from home and Joe raises Finn alone, despite there being no blood relation. Finn goes to Paradiso Perduto every Saturday, where he learns to dance with Estella. One day, Estella (now played by Gwyneth Paltrow) mentions that she has a party to attend. Ms Dinsmoor is shocked that she does not have an escort to take her, to her dismay ("It's the '80s!"), so Finn (now played by Ethan Hawke) volunteers to escort. Estella quickly agrees (though rather annoyed at Ms. Dinsmoor's over-protectiveness). When Finn shows up at the party, he is not allowed in because he is not on the guest list. Estella shows up beside his pick-up truck and asks him playfully if he will take her to his house. Finn agrees. Once they get there, Estella starts to seduce Finn, getting him to put his hands up her dress, and they make out heavily. Then she suddenly leaves, claiming that she is very busy that night. The mention of the party was merely another trick to seduce Finn, showing Estella still makes advances on him, which are also implied to be increasingly sexual.

The next day, Finn goes to Paradiso Perduto, only to be told by Ms Dinsmoor that Estella had left to study abroad in Europe. Finn is considerably upset. For the next seven years he resolutely puts Estella and Ms Dinsmoor out of his mind, along with other high class things like his art. He helps Joe out with his fishing business.

One day, a lawyer comes to Finn and tells him that he will have a gallery show in New York City. Finn and Uncle Joe are astonished at this stroke of luck, not the less because Finn has not drawn ever since Estella left. In the end, Finn is convinced to go to New York, which Estella had once claimed was the art capital of the world. When he arrives, he immediately gets to work drawing again, since he has no pieces to put on exhibit. He sits down in the East Village's Tompkins Square Park, drawing everything he sees and revealing that he has not lost his skill. He takes a break to get a drink from a water fountain - the park's historic Temperance Fountain - and while he is drinking, Estella appears and kisses him. She then invites him to afternoon tea with her at a high class club.

Finn arrives to tea with Estella and some of her high class friends. He only has eyes for Estella, but is rudely brought back to earth when Estella introduces her fianc, Walter Plane (Hank Azaria). Walter teases him by asking how much he would charge to draw a portrait of Estella. He then leaves in a hurry amidst the laughter of Estella's friends.

One day, Finn wakes up in his hotel room to see Estella standing next to him. When he expresses surprise, Estella reminds him that he had wanted to draw a portrait of her. While he prepares his sketch pad and charcoal, Estella removes her clothes. Finn draws many sketches of her naked in different positions. Estella suddenly puts her clothes back on and leaves, saying that she is very busy. Growing sick of Estella's games, Finn chases her out to a cab and asks why she keeps doing this to him. Estella looks sad while explaining through a metaphor that she was trained to act this way by her Aunt Dinsmoor.

Walter shows up at Finn's hotel room one day, wanting to see the result of the portrait session, and is blown away at the nudity. He then confesses to Finn that he thinks Estella is using Finn to push Walter into asking her to marry him and asks him how to please her, as she was a childhood friend of his. Finn has no idea how to respond and Walter soon leaves.

The lawyer who had found Finn in Florida shows up again, moving Finn to a big studio where he can work on his art more comfortably. Finn quickly fills up the studio with his artwork as the opening date of his gallery draws nearer. He makes Estella say that she will be there.

One night, at an important event, Finn becomes frustrated when Walter draws Estella away when he barely even got to talk to her. He follows them to their dinner at a Chinese restaurant. As the bemused dinner guests look on, Finn asks Estella to dance. They dance for a few seconds and then leave the restaurant. Once on the sidewalk, they run for Finn's art studio where they engage in passionate sex.

Finally, the opening night of Finn's gallery show arrives. He looks everywhere for Estella but she is nowhere to be seen. Instead, Uncle Joe shows up, to Finn's surprise and, to some degree, embarrassment. When Joe accidentally knocks a tray of wine glasses over and tries to clean up the mess, Finn repeatedly tells him with increasing volume to "just leave it." Joe feels that he and his homely manners are an embarrassment to Finn and decides to leave early, despite Finn's attempts to get him to stay. Finn then goes to Estella's abode in New York, hoping to find her there, but instead he finds Ms Dinsmoor there, who had come up to New York for the "special event." When Finn asks if she means his gallery opening, she tells him, no, she came up for Estella's wedding. When Finn becomes upset at this news, she says icily that she warned him when he was a child. At this, Finn tells Ms Dinsmoor that she has broken his heart, the way her fiance did all those years ago in the same way she had revealed her heart was broken. At this comparison, Ms Dinsmoor breaks down and apologizes remorsefully. Finn returns to his studio to find a strange bearded man wanting to see him.

The strange man turns out to be Arthur Lustig. He reveals his identity to Finn in a roundabout way. Finn is at first incredulous, but then he becomes uncomfortable with the old man's presence and implies that he should leave. As Lustig is walking out the door, he hints to Finn that he has knowledge of what Finn wants. Finn thus accompanies Lustig to the subway station, since Lustig has a plane to catch from the John F. Kennedy International Airport for Paris.

While they are waiting for a train, Lustig sees some unsavory and muscular acquaintances on the opposite platform. Finn and Lustig outmaneuver them and get on a train. They think they are safe, but as the train is in motion one of the old acquaintances comes through the car and brutally stabs Lustig in the side, stepping off the train at the next stop. As Lustig bleeds to death in Finn's arms, he reveals that he has been Finn's benefactor, paying for the lawyer, the gallery, the studio, the plane ticket, and even buying every single piece that Finn had up at the gallery. This was in return for the kindness that Finn showed to him as a child.

This news, along with Estella's wedding, is too much for Finn. He detaches himself from everything and goes to Paris to study art. He becomes successful in his own right, and eventually he goes back to Florida for a visit. There he visits his Uncle Joe and reconciles with him. Ms Dinsmoor has long since died and Paradiso Perduto is decrepit and falling down, and scheduled for demolition, but he decides to visit her house anyway. As he is sitting in the garden, he thinks he sees the apparition of Estella as a child (though this one is laughing and smiling, a contrast to the haughty, grim-faced child he once knew). He follows the little girl through to the back dock where he finds the child's mother, who turns out to be Estella. Estella had since gotten divorced. She admits that she has often thought of him, and asks for his forgiveness for all the cruel ways that she had toyed with him in the past. Finn forgives her completely, and the movie ends with them holding hands and looking out over the sea.
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