A/N: I had some ideas for one-shots based on my previous story, but somehow I needed to get out of my chest first what I think would be another probable outcome for AYITL. I'm delighted to be back in the Lit universe, hope you enjoy it!

11/23/2022, Chicago

1. Snow Storm

Rory was crying at the American Airlines customer service desk at O'Hare. Hundreds of flights across the country were being cancelled due to the mother of all snow storms, and she couldn't believe that there was no alternative for getting out of Chicago. There was a big chance that she wouldn't reach Stars Hollow the next day. Rory felt like the worst mother ever – her daughter would be eating Thanksgiving dinner without her. Granted, Lorelai and Luke would take great care of her, but she was already feeling guilty about having spent the last six months traveling constantly between Los Angeles and Stars Hollow. Nearly two years ago Doyle had pitched her book to several networks, and CW had bought the rights – Gilmore Girls was going to become a TV series. Rory had accepted to consult with the scriptwriting team (although her novel was no Harry Potter, which meant that she had absolutely no control about the final outcome), but never could have she imagined the hectic industry's production times – it had been years since she had been swamped by crazy deadlines. The scripts for the first season were already late, and she had spent the best part of the last two months away from home. Her daughter had behaved amazingly throughout the whole process, and as Lorelai had put it, the latest 5 year-old who had been as cool had been Rory herself. But she couldn't help but feel like she was missing out too much of Anna's life lately, and the blizzard didn't help.

"Miss, you'll need to make room for the next customer, everyone here is in the same situation as you are, and there's nothing we can do."

Rory left the desk teary-eyed and defeated. She was stuck in Chicago for who knew how long. Damn connection flight. She took a deep breath, grabbed her phone and, after a quick call home to confirm that she was definitely stuck, she started ringing the closest hotels in search of a room to spend the night – to no avail. She really shouldn't have spent that much time moping around customer service desks and car rental companies.

"Stuck in Chicago?"

Rory's heart stopped. Even before turning and seeing him her stomach was already doing somersaults. Her face was probably swollen, and she wasn't wearing waterproof mascara – funny how, of all the things she could think about, of all the passion and the heartbreak and the chances lost for them, the first thing that came to her mind when she heard Jess' voice was the cheap non-waterproof mascara she carried in her travel bag and how dreadful she must be looking. Why should she care, anyway? It was long over. Hanging on to that thought with all her might, Rory turned.

"Well, aren't we all?"

Jess' smile was dashing. The years had done him good. He hugged her naturally and kissed her cheek. She hated how relaxed Jess seemed around her since he had married – Rory had never stopped feeling anxious whenever his lips where in the vicinity, so the brief contact had her getting warm in a way she knew she shouldn't.

"It's great to see you, Ror. It's been too long."

Too long, indeed. Their paths had drifted away after Jess' marriage 4 years ago. Their timing had never been right.

"Yes, I've missed my fairy god-editor."

Jess laughed. "I just gave you advice you never really needed. I knew you were going to make it big time."

Rory knew she was blushing. "I truly couldn't have done it without you."

Jess shook his head, and all Rory could notice was his wild, beautiful mane. She repressed a sudden urge to caress it.

"Nonsense. You did it yourself. You should know you're my heroine, so don't sell yourself short."

"Well… right back at you." Rory thought about that punk kid who had endured every punch life threw him and managed to become one of the best people she had known. She reminisced about the two of them sharing their passion for literature over twenty years ago, in what was their brief meeting of the souls. "Who would have thought, right?"

Jess seemed puzzled. "Thought what?"

"Nothing, really."

Jess bumped against her arm. "C'mon."

Rory hesitated while chanting in her mind he's married like a mantra. She didn't want the conversation to reach Rory-Jess levels of intensity. "I was just thinking that it's funny how everything turned out. I've known you for a while, after all."

Jess laughed wholeheartedly. "I see where you're going – you're remembering my teenage hoodlum days, aren't you?"

"I never saw you that way, and you know it."

"No offense taken, Ror, so don't worry about it."

"That's not it – I was just thinking how funny it is that the two of us, who loved books so much, have become writers."

Jess looked at her intently, and Rory's breath caught in her throat. "Yeah, it's funny. Well, not really – it's beautiful."

Melancholy hit Rory in the pit of the stomach like a sea wave. So that was what getting old felt like – like yearning for a future that was once promised, but that would never happen. Jess' stare wasn't faltering, and Rory was hypnotized by it. "And to think that we never talked about it. Wait – did you ever consider becoming an author back then?" Back then – that was Rory's blanket term for when we loved each other.

Jess smiled. "Honestly?"

Rory realized that there were few things that had thrilled her more in her life than Jess' honesty. "Please."

"I did think about it. I thought about it a lot."

"Wow… I'm shocked. Why didn't you tell me? Why didn't I think of asking?"

"I guess… I didn't want to jinx it. What if I said I wanted to become a writer and then never become one? It would have killed me. I was not really hopeful of my possibilities at that stage."

"You know what? I've never said this out loud, but… I did the same, subconsciously. But it was such a deep, ingrained fantasy that I couldn't voice it – not until you encouraged me to write. I still wish you had told me, though."

Jess' face turned serious. "Maybe it was for the best – some things I did say out loud back then were forever jinxed."

So it seemed that back then was a blanket term for painful times to Jess. Rory was taken aback. Somehow, a brief encounter with each other had painfully revealed their deep, convoluted connection – as usual. Rory regretted having been so completely overtaken by Jess' presence as to let the conversation go that way. But she didn't have time to dwell on it – Jess was grabbing her bag and putting it on a trolley nearby, along with his suitcase.

"Are you stealing my bag?"

"Are you sleeping in the airport?"

"It seems that I am, everything's full."

"I know, I heard you over the phone trying to book a room. You're staying with me."

Rory's heart started racing. "Do you live in Chicago now?"

"No, I just gave a conference. My rep managed to book me a room at the Hilton here."

There was no way Rory could be in a room with Jess and not spontaneously self-combust. "I… really appreciate it, but… I don't think it's such a good idea."

Jess shrugged his shoulders and started pushing his trolley. "I got your bag, Gilmore. Seems like you're stuck with me."

She shouldn't, she really shouldn't – but, oh, how she had missed his company. Rory started following Jess, who was walking away at a considerable pace. "OK, but I'll take the couch or the floor, whatever's available."

Jess spoke without turning, still pushing his trolley. "Fine by me."

"And I'll ransack your minibar."

Jess stopped dead on his tracks and looked at her, smiling. "Now we're talking – that's exactly how you ride a snow storm."