The next morning, Rory pushed down the lever on her toaster alarm. She had a mild headache, and she suspected it was due to get worse later in the day. Her pillow was blotted with the make-up that she hadn't bothered to take off when she got home. It wasn't until she had dragged herself to the kitchen to get a glass of water that the weight of the previous night became fully apparent to her. All of the emotional baggage that she had spent so long trying to bury had, in the course of one night, been dug up, opened, and unpacked all over the place. She had never had any desire to deal with this at the best of times, and certainly didn't want to deal with it when she had less than a year to go of her PhD. She downed the water and poured another glass, hoping that she could salvage some productivity despite the lingering invasive thoughts about Jess.

After lunch, she sat back down in front of her laptop, with the aim of getting another 1,000 words of her dissertation written before the end of the day. She sighed and took a swig off coffee, trying to put off, however slightly, having to work in the face of all the monumental distraction. She had gotten through a paragraph – about half of which was actually usable – when her phone buzzed. Against her better judgement, she pulled it out of her pocket to check the message.

She didn't recognise the number, but based on the contents she had a fairly good idea of who it was. She checked the group chat that Lorelai had put together to organise a dinner for Luke's last birthday, and had her suspicions confirmed.

"Why aren't we dating?"

She stared at the message in disbelief. What kind of a question was that from someone she only saw about four times a year? Why would they be dating? How could he even ask that? Why couldn't she stop smiling?

Jess was sitting in a coffee shop, bouncing his leg and staring at the 'read' notice on his phone. He bit his lip as he realised that it had only been two minutes. It felt a lot longer. He resisted the urge to throw his phone into the Charles, head back to Philly, and avoid Star's Hollow for the next half-decade. His therapist's voice echoed in his ear: "Awkwardness can't kill you." His mouth was dry and he felt like he might throw up, but he just had to ride it out until she replied and shot him down. Assuming she replied at all.

He was entirely blindsided when his phone started ringing. He took a deep breath, his hands shaking, and answered the phone, trying to sound aloof. Or at least not catatonic.

"Hello?"

"What the hell is wrong with you? Why the hell would we be dating? What the fuck are you talking about?"

"Rory, hang on, just hear me out, there's logic behind my insanity for once."

"Yeah, insanity is the right word, mister." Jess let the silence linger for a moment. Rory was the one to blink first. "Where can I meet you?"

An hour later, Rory entered the coffee shop. Jess put his laptop in his bag and stood up to make sure she could see him. She waved at him curtly, and stopped at the counter before coming to sit opposite him.

"Thanks for coming," Jess said.

"Well, I love a good mystery, and that text was the best I've seen since the Lifetime dramatization of the Yuba County Five."

Jess chuckled. "You're always on, aren't you?"

"Jess, what's going on? What did you mean by that text?"

He shifted forward in his seat, and looked intently at the young woman opposite him. "I know the message was intense, but I wanted to cut to the chase. And I wanted to make sure I got your attention."

"You wanted to cut to the chase… What chase?" Rory .

"Just what I said. We didn't get back together at Yale because you couldn't count on me. Nothing happened when you came to Philly because you were in love with Logan. When we were younger, I was a wreck, and you couldn't count on me, and I get that. I wouldn't have taken me back either. Then we grew up a bit and you were with Logan. We've kept each other at arm's length ever since, to keep the peace, to let Luke and Lorelai have their happy, emotionally functional family. But last night was – look, Rory, I've been doing well lately, I've been doing really well, and even then, last night felt like I was awake for the first time in years."

"I know, Jess, but – but we can't just pretend that none of that ever happened."

"That's not what I'm asking, Rory. I know just as well as you – maybe better – that all of that happened. But I think you've seen that I've grown up since then. You've seen me at work, you've seen me with my sister, you've seen me repay Luke in all senses of the word. I'm dependable, you're single, and last night we allowed ourselves to reconnect. It just seems to me that all of the reasons we weren't dating before aren't there anymore."

Rory sat there, stunned.

"If you look me in the eye now and tell me that you have no interest, if you didn't mean anything by asking me those 'what if' questions last night, if you don't want to know what it might be like with us, I'll buy you another coffee for the road, I'll see you for April's 21st birthday, and I won't bring it up again."

She stared down at her coffee, knowing that she wasn't far off crying.

"I guess – I did mean it, last night. Part of me has always wondered. And you're right, last night was incredible. And I'm sitting here now and I can't believe this is really happening, that you're here and I'm here and we're having this conversation. It's just – I'm scared."

"Scared of what?" Jess maintained a calm façade, still feeling like he might vomit at any second. That third espresso was a mistake.

"Jess, if we do this, it's not gonna be like a new relationship. It's gonna be intense, from day one. That's not to say it'll be bad, lots of intense things are good, like Grace by Jeff Buckley, or that scene from Trainspotting, or – "

"Rory." Jess reached across the table, holding her hands to steady her.

She sniffled, tears now welling in her eyes. "If we break up, it'll be catastrophic."

Jess closed his eyes and nodded. "I know. And I'm scared too. Look, Rory, I can't promise you that this will work out, and that we'll be together forever. I can't promise that we won't get hurt. But I can promise that I'll be better than before. I just know that if we don't give this a shot now, I'll never get over the regret of walking away from you."

Rory let a few tears fall down her face. After a few moments, she looked up at Jess, and asked "If I say yes, will you still buy me a second coffee?"