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The first time Remus sees him, he is a sullen well-dressed boy waiting on a train platform. From what he overhears, he is being coldly informed of the proper behaviour expected of him as a member of the Black family.
The first time Remus realises he has a friend is when he is hauled up unceremoniously by the back of his robes and handed his books after being tripped in the hallway by two older boys with malicious eyes and green and silver scarves.
The first time Remus tells him he loves him; it isn't to him at all. It is to a photo sent with a care package involving treats from Hogsmeade and a letter speckled with misspellings and chocolate stains telling him that they have managed to perfect their transformations.
The first time Remus resigns himself to never having him the way he wants him is when he accidentally walks in on an amorous Sirius and a stunning French girl on the night of their Yule Ball in 6th year.
The first time Remus loses him is when he is pulled back from a mission and gravely told by Albus Dumbledore that Sirius Black has just been arrested on charges of murder and colluding with the Dark Lord.
The first time Remus lets himself think that perhaps things might go well, that he doesn't need to loathe himself for losing his heart to the murderer of his best friends, is the night Buckbeak flies free.
Remus thinks being cautious with what you say and do is a good trait that has served him well and kept him alive. But the first time he hates himself for it is the day after he loses the person he has loved for most of his life to a veiled arched doorway.