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Harry Potter: Albus Dumbledore
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In Goblet of Fire, Harry develops his first crush, on Cho Chang (though there are hints of it in Prisoner of Azkaban). During his fifth year he has an on-and-off relationship with her and even kisses her under the mistletoe, but they split up at the end of the year. Technically this break-up is as a result of Cho's friend Marietta Edgecombe's betrayal of Dumbledore's Army, but at the time this occurs their relationship is already faltering; they are simply not on the same wavelength, as Harry is quite clueless about how romance is supposed to be gone about in general and is unable (or indeed, unwilling) to deal with Cho's grief at the death of her late boyfriend Cedric Diggory or comically misplaced romantic jealousy of Hermione.
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Dumbledore began giving Harry private lessons with the Pensieve. They took journeys together into various individuals' memories concerning Voldemort. Dumbledore surmised that to ensure immortality, Voldemort splintered his soul into seven fragments called Horcruxes. Five pieces were placed into common objects and two into living objects. Two Horcruxes were previously destroyed (Tom Riddle's diary and Marvolo Gaunt's ring). Harry and Dumbledore retrieved a third Horcrux, a locket, hidden inside a seaside cave, although Dumbledore is weakened to the brink of death by the effort.
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Harry has always been isolated and alone. He has lost his parents, his godfather, and finally his last protector, Dumbledore. He tends to lean to towards Remus Lupin and the Weasleys whenever he needs help or advice. Mrs. Weasley in particular is something of a mother figure for Harry, and she treats him as any one of her sons. At other times, Hagrid will offer support to Harry but as he progresses as a teenager his relationship with Hagrid diminishes ever so slightly.
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Albus Dumbledore