Rumpelstiltskin (Rupert Gold)
Rupert waited every single day for the gap in between his chemistry class and Business 101. Every second of his day revolved around that three minute break in between periods. He got to take a shortcut through the library on the way to business, where the prettiest sophomore in school, Belle, spent practically every waking moment.
They dated throughout freshman year, but lost each other due to the curse of summer. They saw each other a few times in the beginning of the year, going out to the diner near Storybrooke High for iced tea and burgers. Rupert encouraged her to sign up for the student volunteering job at the school library, and he had even helped her through a rebellious phase of hers. But they were different people, very much so; she somehow managed to be nerd and beautiful, while he somehow managed to be a loner yet feared by everyone in school. He had a thing for gossip, it couldn't be helped. The only time Belle appreciated fabrications of the truth was when they were embedded on the soft pages sewn together by binding, protected by a brand new hard cover. He couldn't help but wonder what she saw in him for that long amount of time they had been together.
He passed through the library and waved to Belle, who happened to be stacking a pile of Stephanie Perkins novels in the romance section. The very section he so desperately yearned for their story to be shelved. Unfortunately, the only law of the library that their relationship adhered to was silence. He waved to her, and she waved back, only to return immediately to her books.
She didn't see anything worthwhile in him. She looked past everyone's flaws and saw a person worth loving.
That was why he was so tragically in love with her.