Home for the Holidays
"Rory?"
"Jess," Rory turns her eyes from her drink in front of her and looks up at his familiar face.
"Mind if I sit here?" he asks and motions to the seat at the bar next to Rory. She shrugs and turns her attention back towards her drink. The bar is packed; she isn't going to read too much into Jess wanting to sit by her. Besides, it's not like they were on bad terms. They just hadn't really interacted much over the years beyond polite chitchat at family events.
"Could I get another double screwdriver please?" Rory asks the bartender when he comes over. Jess orders a drink and tells the bartender to add Rory's drinks to his tab. "Jess, really, you don't have to do that. I ordered food earlier and I'm perfectly capable of paying my own bill."
"I know. Don't worry about it. My treat," he says with a soft smile and Rory shifts a little uncomfortably in her chair. This was getting to be their longest conversation in years, since Rory ruined any potential of a friendship in Philadelphia all those years ago.
"Thanks, Jess, I really appreciate it," she says quietly and sips her drink. His name feels weird on her tongue, and she isn't quite sure how to continue the conversation. She isn't sure that she should.
"How's it going, Cuz?" he asks and playfully nudges her, flashing a crooked smile. Rory grimaces at the nickname and holds up her glass.
"To being related," she says and clinks her glass against Jess's when he raises his. He gives a big hearty laugh and takes a drink out of his glass of whiskey.
"I guess I can't say I've never kissed a cousin," he says with a wink and Rory isn't quite sure how to feel. This is the first time in years that he's initiated conversation with her and she has always been afraid of initiating. Afraid of stepping on his toes, afraid of going where she isn't welcome, afraid of bringing up the past. So she doesn't say anything, just offers a small smile. "Is that even legal?" he asks with a huge grin on his face for some inexplicable reason.
"I can't say that I've ever felt the need to Google that," Rory says with a laugh and stirs her drink with the straw. "Considering, you know, I don't even have any cousins."
"Besides me," he offers.
"Becoming step-cousins when we're both adults is far different than being biological cousins," Rory says.
"Wait, so you're saying that if you had cousins, you would feel so inclined to look up the legality of first cousin marriages in the state of Connecticut?" Jess says and motions to the bartender to order another round of drinks for them.
"That is not what I'm saying at all and you know it."
"Okay, whatever, Gilmore," Jess laughs and then is silent for a few minutes. Rory is silent, too. She likes the conversation so far; she doesn't want to ruin it. "Wow! I can't believe I've kissed a cousin!" he says incredulously.
"It is what it is," Rory says with a half smile, trying to pass it off as a joking comment but also trying to see if that phrase sparks anything in his facial features. Rory sees his eyes widen for a split second, but then return to normal as he takes another drink. She isn't entirely sure she hadn't imagined it. Jess's face has changed and matured over the years, developed lines and shadows that Rory didn't recognize. But she still knows how to read his face like it was just yesterday that he was stealing her books and writing love notes in the margins.
"Seriously, though, how have you been?" Jess asks her.
"I've been well, actually. I finished up my Christmas shopping a couple of weeks ago and I was able to get a few weeks of work off, with the election over and all. So it's actually been very relaxing. I spent a week in Chicago with Paris, and now I'm back in Stars Hollow. You?"
Jess smirks and nudges her arm before saying, "Are you sure the world can survive without you telling them what Harry Potter character they are based on their favorite TV shows?"
Rory laughs and says, "Okay, you definitely know that's not my job. I cover politics."
"Okay, so what candidate am I based on my favorite candy?"
"Jesus fuck, I never should have told anybody I work at Buzzfeed…" Rory mutters, and then continues, "How are things for you out in Philly?"
"Well, recently I've been very stressed," Jess says with a slight smile.
"Why?" Rory asks even though she knows she probably shouldn't. She knows him well enough to know when he's setting her up for a joke.
"The election. Are you a political journalist or not?"
"Whatever, Jess, I meant at Truncheon."
"Things are going well. We've expanded to a larger location and have hired more people, taken on more authors. It's actually been really exciting recently, with all these big changes. If business goes well, we're thinking of expanding out to New York."
Rory almost chokes on her drink when he mentions New York, but tries to conceal it with a simple cough. "New York, New York?"
She and Jess haven't lived in the same town since they were eighteen. She got butterflies in her stomach just thinking about it, but she has to remind herself that it was the alcohol and that it wouldn't matter anyway. They were kids when they dated. Years have passed and they've moved on. She hurt him last. Rory ruined any chance.
"Yes, that New York," Jess says with a laugh. "But, of course, that wouldn't happen for another year or so, depending."
"Jess, that's really exciting! How's your writing going?" Rory asks. She'd never admit it now that they were more acquaintances than friends, but Rory had read each and every one of his three books multiple times. They were excellent.
Jess's eyes brightened and Rory knew that as much as he loved his publishing company, writing was his real passion. "Writing is going well. I'm trying my hand at a romance novel right now. It's so different than what I've done before, but I think good writers need to challenge themselves. I'm also fortunate that I'm in a situation with Truncheon where I can afford to experiment."
"I think that's really smart. Got any muses?" Rory asks and tries to make her tone come across as light and teasing, rather than genuine curiosity about whether or not he has a special someone in his life. All of a sudden, Jess's face gets serious and he takes another drink.
"Rory…" he trails off. She cannot read his tone or his face for the first time since she's known him. He looks shy, almost. Rory thinks that shy looks weird on Jess. "Could we start over?"
"Start over? Jess, what are you talking about?"
"I mean… I hate this distance between us. Can we pretend all of the bad stuff between us never happened and move on? I mean, I know we're not 18 anymore and we've both led separate lives for so long, and I don't expect things to go back the way they were—in fact, I don't want them to—but I just really want to get dressed up and take you out to dinner and be comfortable enough with you to ask if you'll want to kiss me after the first date and—come on, Rory, what do you say?" Jess looks so hopeful and sincere and Rory just knows that her face has nothing but a stunned look on it.
Finally, she puts out, "I don't date my cousins."
Jess laughs a low chuckle and grabs her hand, "It is what it is. You. Me."
Rory smiles and leans forward to kiss him softly on his cheek.
This is basically my headcanon for what happens a few years after season 7. Obviously it's not revival compliant because Luke+Lorelai are already married, Rory has a job, Rory isn't you-know-what, and Paris lives in Chicago.
Let me know what you think! I'd be happy to talk the revival with you-just shoot me a message.