Jess Mariano had been living in Stars Hollow for three weeks now—the worst three weeks of his life, if you were to ask him. His mother, Liz, tired of her son’s rebellious streak and incomprehensive behaviour, decided there was no better solution to the dilemma than to send him to live with her brother.

She hoped Luke could prove to provide the role of a ‘stern father figure’ that showed him the right way and provided stability with a firm hand.

The town did indeed provide that; stability. Every morning and every afternoon, Lorelai and Rory Gilmore would show up and drink ungodly amounts of coffee. Every other day, Kirk would burst through the door, claiming he’d just made the greatest discovery of the century. Every afternoon, he would see Babette and Patty failing miserably at being discrete as they whispered amongst themselves, shooting glances at him.

Jess liked to pretend he didn’t enjoy the quietness. He rolled his eyes every time Luke told him to serve someone coffee or clean a table—never mind the secret satisfaction that surged in him when a client smiled.

The town hated him still, that much he knew. And he hated them back, at least he thought he did. That was what anyone would have expected.

There was, however, one silver lighting amongst the amber of the trees in autumn. You. Yet another teenager of the town; one with a quick mouth and too many thoughts for a place like Stars Hollow. You talked about politics and philosophy, you talked about the world. Stars Hollow was too small for your ambitions, and that’s something he realized without you having to tell him.

So you bonded in that regard—hate for the small town and the desire to be more. He told you about New York and watched how your eyes shined with all the possibilities the city offered. One day, he’d say, once Luke had got off his back, he would take you there.

The sun had just set, it wasn’t actually late, but the chilly October air sure made it feel like it. You sat in your bed, a book in your lap, you chewed on your pencil as your brows furrowed. And there, a knock in your window. Outside, Jess. His hair was disheveled, likely from the wind.

You gave him a puzzled look before allowing him in, “jeez, it’s freezing out there.” He plopped down on your bed, resting his weight on one arm.

“Before you even complain about me sneaking in, I got panckakes.” He pointed towards the bag he had just placed on the floor. “Don’t let Luke find out, though, I’m not supposed to give food for free.”