A/N: This story seems to take as long to write as it takes for Jess and Rory's romance to unfold. We are lucky in one regard — as the story didn't have any 2020 or 2021 chapters, I don't think a rewrite that incorporates pandemic details is needed at this stage :)

To anyone who has been waiting for an update: sorry to keep you waiting, and thanks for still being here.

16. Space & Time

August 11th, 2024

The alarm rang, and Anna stirred. Rory hit the snooze button and caressed her daughter's hair. Anna was sleeping through the sound of the zen-like bell ringtone as she would have done on any school morning. But that was not a normal day. It took Rory a while to make sense of their location. They were in a hotel room… But where, again? Sacramento, yes. Rory was touring the West Coast, participating in a few panels and screenings for the second season of Gilmour Girls, and Anna was with her. Rory had been away from home for too long in the lead up to the first season, and this time she had organized things differently. The show producers had arranged a babysitter for Anna while the panels were on. So the tour had become the perfect excuse for a mother-daughter trip, and they were making the most of their time before Anna's return to school.

Rory went back to Jess' last email, which she had received last night, and reread it for the 20th time. Of course, she wanted to see him. And soon. To hell with their epistolary relationship. Who were they, Tom Hanks and Meg Ryan in You've Got Mail? Rory had fantasized about Jess for many years. Something had to happen already. But she wouldn't be able to see Jess for a while, not at least until being back in Stars Hollow. She wanted to get back to him soon. She didn't want to leave him waiting, not when things seemed to be finally lining up for them. Rory dared to wish. This could finally be their chance. It had been too many years of their recurrent dance —their attraction pulling them dangerously close, only to be pushed away from each other time and again. The alarm rang over, and Rory had to make a conscious effort to stop daydreaming.

"Anna, wake up. Our van will pick us up soon."

It took Anna a while to open her eyes, but when she did and realized where they were, her face lit up.

"Is San Francisco next? Please, can we go to Alcatraz?"

Rory frowned. "Mmmm. I'm still unsure about it."

"I swear I won't have nightmares afterwards."

Rory looked at Anna. Her daughter was sensitive, quick to attune to other people's suffering. Rory didn't think going to Alcatraz would be a great idea for her. She wondered if Lorelai would have agreed if it had been young Rory asking. She thought that she probably would have. Not because of carelessness —although maybe a little, but especially because Rory wouldn't have been scared by it afterwards. Anna was incredibly smart, but much more empathic than any of the Gilmores had ever been. Rory wanted to convince her not to go, but she needed a coffee first.

"OK. Why don't we get ready, and discuss it on the drive there?"

"Cool. Is Mark driving us again?"

"I sure hope he is."

"Nice. He still needs to tell me everything about changing a wheel and taking care of the motor of a car. I'd hate to have a car one day and not know about these things."

"Well, I hope you learn soon. Your mum is pretty useless at it."

Anna played with the frills in her pyjama top. "I'm sure you'd be great at it —if you were more interested."

"Is that so?"

"Absolutely. That's why I'm trying to be more interested in new stuff, that way I'll be able to learn lots of things."

Rory smiled. She couldn't believe how much more intelligent, kind and creative Anna was than she or anyone she had ever met. She felt incredibly proud.

The driver accompanied Rory and Anna inside Hotel Drisco, a beautiful Edwardian building perched atop Pacific Heights, and left them at the reception queue with their luggage.

"Can we leave the bags in the room and go straight to Lyon Street? It's very near."

Rory exhaled. "Yeah, I guess the sooner the better. The prospect of climbing a thousand steps is not going to get more appealing as time passes."

"Hooray! I want to pick the craziest colored house to live in. What will you pick?"

"Biggest, most weird-shaped swimming pool. With an Edward Scissorhands type of garden, ideally."

Rory and Anna were next in line. The man in front of them was taking a bit long to check in. Suddenly Rory's heart started beating faster, and she felt a sense of trepidation. It took her a few seconds before her brain had time to register that it was Jess in front of her, talking to the receptionist.

"If there are any cancellations let me know —I'd like to stay here ideally since I have my reservation for tomorrow, but I'll look for an alternative in any case. I completely messed up with my booking."

"Sure, mister Mariano. We'll call you if a room becomes available, although we don't release reservations since we have a late check-in —so it is unlikely."

"Thanks anyway. Have a nice day."

Jess grabbed his tattered duffle bag and stepped away from the desk without seeing the Gilmores. He took his mobile phone out of his back pocket, while Rory decided to make herself present before he could make any calls —it would be so awkward if he saw her standing there, frozen while trying to come up with something witty to say. She spoke the first thing that came to mind.

"Stuck in Chicago?"

Jess seemed to hesitate before turning, but when he did, he sported the most dashing smile. The mood couldn't have been more different to that of two years ago, when they had met each other at O'Hare's airport and spent the night talking and playing paper basketball. There was another significant difference.

"Who is this man, mom?"

Anna was grabbing Rory's hand while trying to hide. Her daughter hadn't seen Jess for a long while, so it made sense that she didn't remember him. Rory had been so excited that she hadn't even realized that she had dragged her daughter up to where Jess was standing. Luckily her mother instinct kicked in —she quickly put on the me? I'm not on love with Jess facade, almost as fast as she would have said yes if Anna had asked if Santa was real.

"This is Jess, Luke's nephew, remember?"

Anna shook her head shyly. Rory feared that the situation would be too awkward for her daughter and that she would miss the chance to talk to Jess, at least for a little while. But then he kneeled and started rummaging around his bag.

"Hey Anna, could I ask your help with something?" Anna looked at Rory for encouragement before nodding. Jess took out of his bag a paper bundle. He unwrapped it, and a really weird looking teddy bear came out. "So I just gave a conference at Berkeley, and someone gifted me with the University's mascot. It's so funny looking that I thought it must have an amazing back story. Can you help me figure out which one? You seem pretty intuitive for these kinds of things."

Anna smiled and grabbed the toy that Jess was handling her. "Can the back story not have clowns in it?"

Jess looked at Rory before replying, as if he wanted to let her know that he remembered, and that he had her back.

"Of course. Don't feel obliged to include them."

"I do, in a way. Nobody likes clowns anymore."

"You know what? I do. And I'm not scared of them, not as some people are. Why don't I make sure to include them in one of my stories, so you can forget about them for a while?"

Anna looked at Rory and then at Jess, hopeful. "Are you sure?"

"Definitely. I think clown visibility is a very noble pursuit."

"Done deal! Then I'll come up with a story for the mascot. Can I change its name?"

"Sure. Names are very important to the back story. They tell us where the character is from, so if you want the story to be original, I think you really should give it a name of your own."

"Oh, thank you, Jess. Can I make a costume for it too?" Jess nodded but seemed to get distracted looking at Rory, who was beaming. "Do you want to climb the steps with us, Jess? You could leave your old bag in our room, since you don't have one."

It took a while for Jess to respond, who seemed to had lost his train of thought while smiling at Rory. "Yeah, that would be great". He then turned to Anna. "Are you sure you wouldn't mind?"

Anna replied distracted while caressing the mascot's face. "Of course not. It's good to have someone in the family who's not afraid of clowns."

Jess grabbed his duffle bag, and after Rory checked in, the three of them headed for the room, while Rory prayed for her knees to not give way.