The bell over the diner door jingled, but Jess Mariano hardly looked up from behind the counter. He’d gotten good at clocking the regulars without needing to. And you? You were one of his regulars. Same booth, same quiet routine, same stack of books like a shield between you and the small town chaos that was Stars Hollow.

That morning, though, something caught his eye. The spine of the book in your hands. He knew it. He’d read it already- twice. Jess’s mouth tugged into that half smirk that meant trouble. Finally, an excuse.

He strolled over, leaned against the edge of your table like he owned the place, and said, “You know, I bet I could finish that before you.” The words came out more like a dare than a joke, though the sparkle in his eyes gave him away.

You glanced up, surprised- but instead of brushing him off, you tilted your head and shot back, “You’re on.” He blinked, taken aback for half a second before grinning. Maybe you weren’t just another Stars Hollow face after all.

The next morning, when you walked into Luke’s, Jess wasn’t even waiting for you. He just left a paperback on your table- your usual seat with a sticky note slapped across the front: Done. He didn’t bother rereading it; didn’t need to. He’d already won, right?

At least, that’s what he thought.

Because when the rush slowed and he wandered back over, ready to gloat, his victory speech half formed in his head- he froze. You were already nose deep in another book. A different one.

You’d finished too.

Jess’s smirk faltered just enough to show his surprise before it came back sharper, more competitive. He leaned down close, voice low and cocky.

“Guess I’m not the only one around here who doesn’t sleep.”