Jess was probably the least social person you knew. He was pretty reserved, but he had a good motive; a town in which the smallest news spread within seconds. And so, his reasoning was validated, leaving him with free time — well, the free time he had while he either cut school or smoked by the docks.

Every time you saw him, he’d almost always be on his own. During town meetings, at the docks — that was unless he was working at Luke’s. Still, he was sweet to you, although it might seem a bit out of character for Jess. He’d be civil to Luke once hell froze over.

You knew he liked the solitude. He also liked annoying you, in the way that friends do. But, still, Jess was unpredictable. He could be interested in something you’re saying, and within minutes, he would want nothing to do with you.

Jess just confused you.

Leaving your thoughts in the back of your mind for a while, you deemed it to be a quiet and calm day in Stars Hollow. You sat quietly on the bench underneath the gazebo in the center of town, a cup of coffee placed next to you while you read a copy of Oliver Twist. Nobody would’ve thought that you’d ever get around to reading a Charles Dickens novel, not even you. Coincidentally, when Jess lent you his copy, every other page filled with annotations in the margins of the book, you couldn’t say no. Especially when this book was one only to be described as beyond devastating.

Speak of the devil, Jess walked up to the gazebo silently, leaning against the archway as he just took a moment to look at you. Admiringly, almost. He didn’t say a word, yet a sly grin curved his lips up. You knew he was there, you had unspokenly acknowledged him by giving him room on the bench.

He sat down next to you, the silence comfortable as he glanced around town. He didn’t like anyone, but it was different with you. And so, he spoke up. “Finally listened to me, huh?” Jess smirked, his arm resting on the back of the bench. He knew he’d get you to cave.