Title: "Goodnight, Mr. Caulfield."

Rating: PG-13.

Summary: He doesn't know whether Stars Hollow or Lorelai will ever fully accept him, he figures he can reason with Lane, but he wonders whether the past ten minutes, most of them spent in silence, is enough to make up for it all.

Authors Note: Don't ask where it came from.

Dedicated to Lee, 'cause she likes what she's seen. And 'cause she's awesome. Duh.
The old steps of the porch creak when he returns from his late night adventure. He doubts it will wake anyone up (in Stars Hollow the creak of a step is comforting, not creepy), but he tries to be extra quiet anyway. Taylor is sure to know it was him by the crack of dawn anyway, but that's no excuse to let himself slip.

There's a chair frozen to the porch, and he pulls his coat around him a little tighter as he sits down in it. The air is so cold he feels lightheaded, but he pulls out a book anyway and begins to read.

Before long the cold drives him inside. He shivers at the first burst of warm air and then puts his hand to his cheek to feel the contrast between hot and cold. It's something he's done since he was a little boy. A quirk he wishes he didn't have.

There's an easy chair by the fire that he settles himself into with a sigh. The last of the embers are crackling softly, but he has tuned them out within seconds, choosing to focus on the words in front of him instead.

This is one of her books, and he notices her handwriting scrawled daintily along the margins every now and then. It's a habit that he knows she's picked up from him, and a tiny part of him smiles every time he sees it. Her words are strong and insightful, but her handwriting is soft and scared. She is still unsure as to whether or not she's destroying her precious books.

He is snapped out of his reading by the sound of rustling paper. He looks over to the staircase to find the source of the noise is Rory's grandfather, an aging man (late fifties?) with the air of a world traveler (a fact Jess knows to be true due to the conversation during dinner). He observes the older man for a moment, while he waits to be seen.

When Richard finally spots him it has been nearly five minutes. The notebook he is holding (a boring yellow legal pad) flies into the air and he barely withholds a scream. Once he has calmed down he straightens up and confronts Jess.

"And who might you be?"

Jess considers this for a moment. On the one hand, he can offer up a smart ass response and then disappear upstairs. On the other hand, he can be polite, get on Richard Gilmore's good side, and win another spot on the eternal scoreboard between himself and Dean. He opts for something in between. A polite smart ass. "Jess."

"Ah." Richard says nothing in a way that says everything and walks over to the sofa across from Jess. "You're a friend of Rory's, are you not?"

"Something like that."

"She tells me you read."

"I've been known to, yes." He shrugs the question off with ease, a practiced art. He is, after all, an artist when it comes to being nonchalant, indifferent, apathetic. He has spent years on it. It took months to get the right eyes, the perfect smirk, the cool demeanor.

"Well, Rory mentioned something about Salinger. I myself am not a fan, but I understand why some people are."

"He's okay."

"I take it you fancy yourself a smart ass, not unlike a Salinger character."

Jess nearly jumps out of his skin at this, a situation that his self-training has not prepared him for. This man, rich, important, sophisticated, just called his bluff...not to mention the fact that he said "ass," and now Jess is left exposed as a fraud, reeling in how true to her roots Lorelai Gilmore really is.

"I take it you've never heard an old man say 'ass,' though I imagine you'll hear it again."

Jess still says nothing. Instead, he sits, staring openly at Richard, and blinks, gape mouthed.

"Rory said you weren't much of a talker."

Jess pulls himself together then, wondering how much Rory has told Richard about him, and, more importantly, why.

"I believe she used the word 'brooding.'"

Jess scoffs. Brooding? It makes him sound dark and mysterious, and he supposes that that was what he was going for. Then again, he had the attitude before he wanted the girl. Isn't that what brooding is all about?

They sit in silence for a few minutes. The inn is full of life and quiet at the same time. Jess can hear Babette's snores (they are definitely Babette's, but he doesn't know how he knows this), even though she is on the opposite side of the building, and he laughs to himself. He wonders if it's possible for Stars Hollow to be anything but Stars Hollow.

"Well, this is quaint."

"Oh, yeah, every Saturday the whole town gets together for a sing-along."

Richard laughs, and Jess is surprised. He thought he had lost a point on his scorecard, but instead he seems to be holding out.

He has always known that being with Rory is never just about being with Rory. There's a network of people (Stars Hollow, Lorelai, Lane, and, of course, Richard) that have to approve, and if you can get past them there's still Rory to win over, with her strong will, powerful wit, and complete disregard for common sense. He doesn't know whether Stars Hollow or Lorelai will ever fully accept him, he figures he can reason with Lane, but he wonders whether the past ten minutes, most of them spent in silence, is enough to make up for it all.

"I should get to bed before my uncle realizes I'm gone," he says and gets up to leave. Richard nods to him, offers up a smile, and he returns it, somewhat awkwardly, as best he can.

"Goodnight, Mr. Caulfield."