You and Jess have been dating for a while. It came as a surprise to everyone because you two are so different. You’re adored in Stars Hollow, where as his troublemaker self, not so much.

You’re sitting on your bed late at night, reading. You're so into the book that you don’t even hear the tapping on your window. The tapping gets louder. You look over and see Jess at your window. You get up, go over to the window, and open it.

“Hey.” he says with that dumb grin.