A/N: Thanks so much for the continued support by way of reviews :)

(For disclaimer, etc. - see chapter 1)

Chapter 13

'Why don't you ask her and find out?'

Noah's words kept on echoing in Jess' head. The kid had really, actually, genuinely told him that he should ask Rory out. It was nothing he ever could have expected, but he didn't hate it. Not that it helped as much as it should.

At forty-seven years old, Jess had grown up a lot, but in some ways, he was as much of a coward as he had been at seventeen. The idea of facing up to his longtime feelings for Rory, of confessing them to her now, it scared the living daylights out of him.

Jess would love to make excuses. Would love to say he couldn't go through with the plan because of Noah, because of Logan, because of circumstances being what they were. Unfortunately, none of that was relevant. Noah had given his approval. Everybody, including Rory herself, had made it clear that she would never, ever get back with Logan, not even if her life depended on it. So, what else was there? What possible circumstances were standing in Jess' way? He even had Lorelai's approval. Literally the only thing holding him back was himself.

"Look at you. Still terrified that she's going to laugh in your face," he told his reflection in the mirror, shaking his head, trying not to notice the silver strands in his hair or the bags under his eyes.

He was growing old relatively gracefully, or so he thought. April even told him he was pretty well-preserved, and though the wording was suspect, he did believe she was being at least a little bit complimentary and as honest as she ever was.

To his eyes, Rory had barely changed at all, even though she would also be forty-seven in just a couple of days' time. In his bag was her birthday gift, the first one he had reason to buy for her in a good long while. After all, this was the first of her birthdays he had been around for in more than a decade.

"Maybe wait until then?" he asked himself, immediately shaking his head again and turning away from the glass. "Idiot."

He knew it was true. Putting off the inevitable never did anybody any good. Sure, ignorance was bliss, and sometimes, it was nice to live in hope for a little while, but reality was always right there waiting. Better to face it than hide like a coward.

Jess hated cowards. The type that Huntzberger was. The type that Jimmy used to be. Jess wasn't that guy, or if he had been, he certainly wouldn't be now. No more running, no more hiding. It was time to lay his cards out on the table and just let whatever happened, happen.

"Now or never," he muttered, strapping on his watch, pulling on his jacket, sparing himself once last glance before he left the diner apartment and headed for Rory's place one more time.

It was Monday afternoon, not long after lunch, which meant Rory should be home alone for a while. It was also a mere twenty-four hours since he was last over at her house. Not that he hadn't seen Rory and Noah in the meantime. They came over to the diner to eat last night and, through pure boredom, or a very deep-seated old habit that just wouldn't die hard, Jess had been bussing tables when they walked in. He didn't exactly have much time to talk.

Honestly, he didn't try that hard, deciding it was better to leave them be. All he really gleaned was that Noah's grounding after the New York debacle was potentially being reduced on account of good behaviour on Noah's part and dick behaviour on Huntzberger's side of things. That and a reminder he didn't need that Rory's birthday was coming up.

October 8th. That was just two days away, and yes, he had factored that in when he decided to come visiting. Not that Jess had intended to sweep her off her feet for the big day or anything. He just brought her a gift and hoped she liked it. Right in that moment, he only hoped she would accept it, especially if today's experiment, for lack of a better term, didn't come off.

Finally outside of the house, Jess tried and mostly failed to take a very deep breath, wondering not for the first time in his life why he always reverted to smoking when he got nervous. Not today, because the last thing this interaction needed was bad breath or accusations of falling down on bad habits he was supposed to have kicked long ago, but recently, unfortunately, and a lot in the past. He really was getting too old for being so dumb.

"Okay, just do it."

Jess rolled his eyes at the phrasing, aware that he sounded way too much like a sneaker commercial, as he stepped up onto the porch and rapped on the door, quickly, before he had a chance to change his mind again.

"Hey." Rory's smile was big and bright as she opened the door, whipping off her glasses in a second. "I was just working, but it's fine. I mean, it's all flexible and everything, I don't have to be working now."

"I didn't mean to interrupt or anything," Jess told her, realising too late that he was probably gabbling as fast as she was. "I just needed to talk to you."

"Then come in," she insisted, moving aside and ushering him into the house.

She seemed weirdly nervous, almost as if she knew why he was there. Of course, there was a chance that Noah had said something. He had no qualms about encouraging Jess to ask Rory out, why not also tell his mom that the offer might be forthcoming?

Jess wasn't sure if he felt better or worse for knowing Rory might have pre-prepared an answer. Either way, she hadn't slammed the door in his face or anything, so he chose to take that as a good start, maybe even a good omen.

Sitting down on the couch when she offered him the chance, Jess watched Rory tidy her work papers and laptop away, waiting for her to be comfortable in her chair before he started.

"So, you wanted to talk," she reminded him, her head tilting a little to one side as she stared at him. "Should I be worried?"

"No, obviously not. Why would you think that?"

"I don't know." Rory shrugged, almost seeming to laugh at herself in the next second. "Honestly, the way things have been going lately, it seems to save time to start worrying before the next crisis happens. Not that you coming here would automatically bring on a crisis. If anything, you've been a really calming influence in the chaos."

"Wow. That's not something I'm used to hearing," he told her honestly. "Not in Stars Hollow anyway."

"Well, there used to be reasons why people thought you were the opposite of a calming influence," she pointed out, with a smirk to rival any he had ever worn himself. "But that was a long time ago."

"It was," he agreed, almost glad for the easy in to the time they shared together way back when, "and I know I wasn't always the greatest person to be around back then, but I also like to think that we had some good times. That something good came out of us being together, back then."

"Of course it did. I know it did," Rory insisted, nodding her head. "Jess, please don't ever think that I regret anything about the past we've shared. I don't. I know things got bad for a while, but there were reasons. We both handled things badly, because we were so young and, well, we just didn't know how to be better. We've really moved on since then. I mean, shouldn't we have? It's been thirty years!"

Those words gave Jess pause for thought. The past was long gone, long over. They should've moved on. He should've moved on, but he hadn't. In a lot of ways, he had, when it came to how he felt about his childhood, his parents, a whole bunch of things, but not Rory.

When he got around to thinking about her, sure, things were different, but his feelings never changed. He loved her. He always loved her. That was probably too much to come out and tell her, but Jess wasn't really sure there was another way to do this. Noah talked about just asking Rory out, like it was that simple. He had no idea that nothing ever had been with the two of them. Not once.

"Jess?"

The look on her face was pure worry. He had seen it before, other times, way back in the dim and distant past when he looked too serious, stayed silent too long. She hated that she couldn't reach him, couldn't help him. She told him as much, and after that, he had tried to be more open, tell her things, share what was on his mind.

It never came easy, not for years, and by the time he was in a place where he was ready, really ready to be what she wanted and needed, it had all seemed too late. Time and again, he thought he saw a chance, and the window snapped shut before he dared to take the leap. Not this time.

"Rory... This is going to sound crazy, believe me, I know, but there's something I've been wanting to tell you for a while. That I need to tell you now because... because life has a habit of throwing curves balls, and I'm starting to feel like if I don't say it now, I might just regret it, again."

"Okay." Rory nodded. "Then whatever it is, just tell me. Jess, you know there's nothing you can't say to me. After all this time-"

"I love you," he told her fast, just ripping off the band aid before he lost his nerve all over again. "And I know that's probably a given, after all the time we've been in each other's lives, and all the ways we're connected and everything, but that's not what I mean. I'm saying that I love you, the same way I always loved you, pretty much from the first second I saw you. I know it's been a million years since I said it the first time, and you probably think this is the weirdest thing, maybe even the saddest, stupidest thing, I don't know, but it's the truth. I have been in love with you this whole time and I'm pretty sure I'm not going to stop, so... there it is."

He wasn't sure what reaction he was expecting. Tears, laughter, shock, incredulity, even anger, anything at all would have been acceptable, Jess supposed. After all this time, all the opportunities both taken and missed (mostly missed), all the things they had gone through, the ups and downs, together and apart, but it was still true, just like he said.

Jess loved Rory, loved her so much he sometimes wondered if it would be the death of him. Finally, he told her, just as he had so long ago, when they were only nineteen years old. At least this time he was staying to see and hear her response, whatever it might be.

To Be Continued...

A/N2: Yes, I know, kind of a mean to leave it there BUT if I had continued... well, it kind of would've ruined the plan I have for the next chapter and also made this chapter stupidly long. So, sorry if you're disappointed by this update, but rest assured, there will be another next Friday, just like always ;)