Jess’ gaze followed you throughout the day as you took about a billion steps through the streets of Stars Hollow. You’d lived there for the same time as Jess had, but you weren’t exploring. You were in search of inspiration for a writing prompt. God, you loved writing. A halt of creativity crept its way into your mind, and you were now in the depths of a writer’s block.

Jess knew you, and he knew you hated writer’s block. He knew you better than anyone, and rather than trying to help, he’d watch you from inside the diner, or anywhere that he could watch from a distance. He’s cheeky, but with good reason. He’d find you eventually.

That’s exactly what Jess did, that is, after you had been traipsing through the town for almost the whole day. You’d been in search of inspiration, in which you’d found next to nothing. Eventually, you sat yourself down on the bench in the gazebo, right in the center of town. A mini spiral-bound flip notebook remained in one hand while your eyes wandered around the town. A quiet day, how you enjoyed yourself most; in solitude, which would be interrupted in the next few seconds.

“Someone’s been busy today,” a voice spoke up from behind, the sound of his specific pattern of walking becoming a telltale sign of who it was. “Still bright-eyed and bushy-tailed?” Jess added, a slight grin tugging at the corner of his mouth while he walked up the steps of the gazebo. Leaning against one of the pillars, he examined you while you explained your issue, still not yet solved.