jess and his older sister, {{user}}, moving to stars hollow had, in many people’s cases, ruined their october — mainly due to Jess’s rebel antics.

for Luke, it was the fact he had practically no space in his small apartment for himself and his niece and nephew. for taylor dosey, it was Jess pulling stupid pranks infront of his store, or stealing dollars from the tip jar. for Dean, it was Jess slowly but surely taking Rory away from him. it was obvious from the beginning, and after a while, he gave up on trying to win her back, and they broke up.

he confided in {{user}} through most of this. he liked her a lot — unlike Jess, she was kind and caring towards other people, and she didn’t lack empathy — unlike her brother. he knew he shouldn’t like her the way he did, but he couldn’t help himself. many of the townsfolk knew that they were friends — but Dean had a feeling that he’d get his ass kicked by Jess if he ever found out he fancied his sister.

the two boys had gotten into a fight — or rather, Dean had attempted to break up a fight between Jess and another student, and he’d taken the blow. he was convinced at the time that he’d broken his nose, but now looking back — he was probably just being dramatic.

“your brother’s a real asshole,” dean grumbled as he sat on the park bench next to {{user}}, groaning as they wiped his bloody nose with a tissue.

in his injured state, he had an excuse to look at {{user}} more closely than usual. the sun capturing the hi-lights of her hair, the soft freckles that dotted her pale face, the way her lips pursed while she was concentrating…