He'd been there a number of times at various points in his life, but Jess still didn't know Boston very well, so he followed Rory's lead. She lead him to one of the few true dive bars she'd managed to find in Back Bay over the last 5 years. They took a seat at the bar, and sat in awkward silence for a few minutes after their drinks arrived.
"It's been a while since I've been out in the city – I've just been spending most of my time out in Cambridge lately."
"Hard to get too far away from your room with that big deadline looming, huh?"
"Yeah, it's all starting to become very real." Rory smiled and tucked her hair behind her ears.
"How's all that going? Your thesis?"
"Um, yeah it's going fine. It's hard, but I'll get it done." Rory stared at her wine.
"Rory." Jess said. She looked up at him, waiting for the follow-up. "I'm a books guy. Tell me about your dissertation. I want to hear about it."
That was enough to break the ice. Rory started off by giving her bog-standard summary of her research, until Jess pointed out that he had heard the latest update of that less than a year ago at Lorelai's birthday. "Give me the details," he insisted. Soon, she found herself in the middle of a debate about the legitimacy of her case studies for her argument – "It's not just for academic convenience, I really believe I'm getting at something! There's a connection there!" – with Jess arguing about the penchant for academics to overanalyse things – "There's no way that you can know that that's what Jack London was talking about, and I don't think he was!" "You haven't read it as many times as I have." "Yeah, and it's probably on the fourth re-read that you started imagining things!"
It was invigorating, the most stimulating conversation Rory had had in a while. Other academics weren't going to criticise the dissertation of a fifth year PhD, preferring to wait until it was published to points out all its flaws. It wasn't denigrating criticism either – more like healthy debate that only made Rory more confident in her own position.
"Well Ms. Gilmore, I think it's safe to say that you are fully prepared to defend your dissertation when the time comes." He raised his glass, and she matched the gesture. It had been about 45 minutes since they'd arrived, and between the drinks and the conversation, they both had a good buzz going.
"So, Truncheon is opening a new office, things must be going well?"
"Yeah, I manage to make rent."
"I'm a books girl. Tell me about your business. I want to hear about it."
Jess smirked back at her. "It's going well. We've picked up some promising names in the last couple of years, their stuff has been selling pretty well. There's this one book, When You See It, by – "
"Yeah, by Jeff Jones, I read it just before Christmas. It's amazing."
"You been keeping tabs on me?" Jess asked. Rory blushed, entirely unable to think up a comeback.
"It's good to see you, Rory." Jess's sincerity was surprising, but not unwelcome.
"It's good to see you too. You look good. You look happy." She saw him look at his watch. "You don't have to leave, do you?" She didn't mean to seem so desperate, but once again her words got ahead of her.
"No, no," Jess said quickly. "I was just making sure the bar isn't closing anytime soon." He cringed at his own desperation, but Rory seemed unfazed.
By the time the third drink arrived, they were talking like old friends – well, old friends that hadn't been semi-estranged for several years. They covered everything – after work, they moved onto music, books, their love lives, their families. Suddenly, it was a half hour to closing. They ordered a last round, neither of them having any desire to leave.
"This has been great, Jess. This – seeing you, talking to you. It feels like we're 18 years old again. Just with more of this," Rory said, gesturing towards her glass.
"I know what you mean."
"Jess, can I ask you something?"
"That sounds ominous, but go ahead."
Rory would never do this sober, but equally she had a feeling that she wouldn't regret it when she woke up the next morning.
"Back in Star's Hollow, when I was at the end of my first year in Yale, and you came to get your car, and you told me…" she trailed off, as she saw Jess looking down at his glass, indicating that he knew perfectly well what he'd told her.
"Why did you leave? Why did you just drive off?"
Jess sighed, still looking down in shame. "I couldn't – I didn't want to make you put up with me. I was ashamed of how I'd left things before, and how I never returned your call when you told me the same thing. I figured I owed it to you to tell you that I felt the same way, so you weren't left thinking that our relationship didn't mean as much to me as it did. I figured by that point you didn't feel the same way anymore, and I didn't want to put you in the position of having to tell me to leave. So I just did."
Rory felt a pang in her stomach looking at the shame in his face and feeling everything she had felt that night of the Firelight Festival all those years ago.
"I – I think I probably still did. Love you, I mean."
Jess smiled. "Yeah, eventually Luke talked to me and convinced me that I should probably give you the opportunity to decide for yourself whether you thought I was a piece of shit. That's why I came to Yale. I probably didn't express myself particularly well then either, but it was the best I could do at 20."
"It's not that you didn't express yourself, it's just that, I didn't – "
"You didn't think I was gonna stick around. Nobody could blame you for that one."
A heavy silence fell between the two. The thought swirled around Rory's brain, totally immune to her efforts to silence it. She felt her heart pounding, her head was spinning from the booze, and the sense of time inevitably marching towards getting kicked out of the bar was palpable. Who knew when she'd have this combination of presence of opportunity and lack of inhibitions again.
"Sometimes I wonder what would have happened if you had stayed after you said 'I love you'."
"I think maybe we would have gone to the Firelight Festival together. And I think maybe it wouldn't have been our last."