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Will Hunting and his friend, Chuckie Sullivan 

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Will Hunting is a troubled young man; he is a genius who is failing the lessons of life. He works as a janitor at MIT.

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When Will Hunting has too many run-ins with the law, and is thrown in jail, Professor Gerald Lambeau makes a deal with the judge to put Will into therapy and put him under his wing to do advanced mathematics.

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While Will Hunting is given this opportunity, he makes Professor Lambeau's goal much harder to reach, as Will refuses to cooperate with the therapist.

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Professor Lambeau running out of ideas, meets up with an old college friend who he thinks can help Will. The first time Sean and Will meet, it doesn't go great, but Sean slowly becomes Will's mentor and friend.

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Sean becomes Will's therapist to try and help him get out of the South Boston mindset. They're both met with challenges from each other, but they make slight progress.

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Will meets Skylar at a bar near Harvard; she gives him her number and they go out. Things go great for them, but afterwards, he struggles to choose whether he wants to go out again with her or not. Will talks to Sean, who gives him advice. Him and Skylar continue to go out.

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Professor Lambeau and Sean arguing about Will

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When Will's life is completely changed in the span of a short time, he starts to question the things he's doing. He knows that his life is going to change, and he's afraid of that change. When Lambeau set up job offers for Will, he would purposefully not go or reject the offer entirely.

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When Skylar asks Will to come to California with her, he makes it clear that he doesn't want to. He becomes afraid that Skylar will realize that he's not enough, and is afraid of the change of setting. When Skylar asks Will if he loves her, he says no, encapsulating this heart-breaking scene.

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When the therapy sessions are close to ending, Sean has to file a report back to the judge. When Sean tells Will of this, they talk about their past. When Sean empathizes with Will, sharing similar pasts with him, he tells Will it isn't his fault, making one of the most emotional scenes in all of cinema. At this moment, Will breaks down, removing the barrier that was hiding his real emotions. This begins his healing process.

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https://youtu.be/GtkST5-ZFHw?si=Il0GmllvcoLCAiWO

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After Will's therapy comes to an end, he tells Sean that he decided to get a job from Professor Lambeau, but later on, Sean gets a letter in the mail from Will. He writes that he's going to go to California to get Skylar back. Will decided that it would be best for him to not stay in South Boston, and to get the thing that he truly wanted: Skylar.