So this update has taken quite a while. Oopsie.

I kind of wanted to rewrite the one-night stand conversation between Rory and Lorelai in AYITL and incorporate it into a timeline that makes sense, so I've attempted to do that here. I also wanted to approach Rory's life on the campaign tour from a different angle and honestly deal with the aspects of her personality that weren't well-suited to her life goals, and how someone like Rory would react to that.

That said, everything that happens here is based on entirely too much freaking research. Yes, I was stalling. I admit it. However, if I know exactly where Rory would have been at any given point on the campaign trail, I might as well put those details to good use.

So here goes nothing. Read, enjoy (or gnash your teeth, either one is fine) and drop me a review if you so desire.

Life on the campaign trail wasn't exactly what Rory had thought it would be.

For one thing, they weren't exactly crisscrossing the country. They started out in New Hampshire, bounced around to Virginia, headed to South Carolina, moved onto Washington DC, and then headed back to New Hampshire. Rory's glance at their upcoming itinerary told her that the next few weeks involved mostly traveling between the battleground states of New Hampshire and South Carolina interspersed with trips to DC. The schedule definitely made sense in terms of managing a political campaign, but she wasn't really being exposed to much she hadn't seen before.

Rory knew New England like the back of her hand, and she'd spent an entire summer in DC as a teenager. South Carolina didn't exactly fit in with the stereotype she had in her head, but the main thing that stuck out to her about the South so far was mostly the sweet tea. She was anticipating the upcoming stops in Chicago and Miami mostly because it was a slight variation to the routine that had been established. She'd had looked forward to this for her entire life, and wanted to cherish everything new it had to offer her.

The truth was that she wasn't sure she liked this kind of life half as much as she wanted to.

She was always losing things. Her hairbrush, her clothes, her spare laptop battery. She was exhausted and seemingly always on a deadline, and the days seemed to be running together. Her articles seemed to be well-received, but she still fretted about doing well enough now that she was a real reporter with real press credentials competing with people who had a lot more experience than she did. She simultaneously felt overwhelmed with responsibility and guilty at not enjoying the experience more, and she was at a loss as to how to balance those two things.

She missed Stars Hollow and her mother, and felt heartsick at not knowing when she would get to see either of them again. She knew her mom and Luke were trying to work things out and needed their space right now, but she still worried about how things were proceeding on that front. She missed her grandparents and their weekly dinners, and her grandfather's quiet yet steady encouragement.

She missed Logan, and spent more time than she would have liked rethinking their relationship. Would she have been happier if she had followed him out to California like he wanted? Would she have been able to handle things better if he had agreed on having a long-distance relationship (at least for awhile) like she had wanted?

She didn't know. She missed talking to him, and worried about how he was adjusting to life miles (and circumstances) away from the life he'd always known. She had gotten so used to the patient boyfriend who listened to her and agreed to factor in what she wanted, and she had wanted their relationship to continue like it was. She hadn't been ready to face the fact that their desires might conflict at a point where their relationship would have to be sacrificed.

She wanted to make the sacrifice on her part be worth it, but it hadn't been at all like she had imagined. Maybe she was drowning in self-pity because of the demise of her own relationship. Maybe it was just that she mourned the loss of the routine that she was used to and the knowledge of how all the different parts of her life fit together. She had lost most of those parts now: it was just her and this job and as much as she knew she should be enjoying it, she was still mourning everything that she had left behind.

She knew she wasn't alone in this. She was surrounded by a coterie of new reporters who shared the same passions and anxieties, and most of them chose to drown their confusion in drinks and strings-free hookups. She engaged in the former but was still holding out on the latter: it just didn't feel like her. At least not yet.

Her hopes rose when she heard that Obama had a speech scheduled for the end of June in Hartford. She could finally visit home, pick up a couple of outfits, check in on her mom and Luke, and maybe make it to Friday Night Dinner. She didn't think she would have time to squeeze in a town meeting or a movie marathon, but she could see the places and people that she knew that she loved and loved her back in return.

Unfortunately, it wasn't to be. The debate between the Democratic presidential candidates at Howard University was scheduled five days after the speech in Hartford, and Rory was ordered to accompany a handful of other reporters to do prep work before the debate. Rory was deeply disappointed, but as a brand-new reporter she knew she couldn't fight this. She never even told her mother that she had the chance to be in the area briefly, although she received several mournful texts once Lorelai had figured out that Obama was scheduled to be in the city.

It was an opportunity missed, but there would be others. Possibly. Hopefully. She wasn't sure she'd be good company right now, anyway.

The week spent in Washington D.C. actually did Rory a great deal of good. She spent most of her time paired up with a fellow reporter named Xavier, who had graduated from Howard University a year ago. He'd bounced around a bit before joining the website in January, and reassured Rory that the disappointment she felt about the job not living up to expectations was completely normal. Xavier clearly wasn't as focused on routine and stability as Rory, who was quickly finding out that her Type A tendencies ran even deeper than she had thought possible, but they still found a lot to bond over. He had been raised by a single mom in Atlanta, and had made it boarding school on scholarship when he was fifteen. He rejected Ivy League offers to attend Howard University, and had flourished. He knew what it was to bridge the hardscrabble and elite worlds, just like she did, and he knew what it was to miss that nurturing environment more than one could have anticipated when the real world came calling.

The last night before the debate, Rory could sense things changing. His smile was wider, his eyes a little more entrancing. Maybe it was the fact that they were isolated away from the other reporters, or that she felt a connection to him from all that they had in common. Maybe it was that she actually felt encouraged that she'd learn to love this a little more from someone who had already been there, or that she'd actually felt excited by this opportunity for the first time in weeks.

Maybe it was none of that, and the bar was serving exceptionally good whiskey.

In an uncharacteristic move, Rory Gilmore fell into the bed of someone she barely knew.

And while it lasted, it was very, very good.

"Are you okay?" Xavier asked her the next morning as they ate breakfast in the hotel lobby just like they had every single morning for the past four days.

"I'm – " Rory was completely stumped at how to explain herself. She felt regret, but she didn't. She had wanted it to mean something more, but she didn't. She thought it would be awkward, but it wasn't.

Sex should mean something more than this, shouldn't it? She felt a bit tawdry and used, but not by Xavier. By the experience. Once again, she found herself trying to feel something that she felt that she should while also knowing that she couldn't make herself do it.

"This is the first time you've done something like this, isn't it?" Xavier guessed.

Rory sighed. "It's that obvious, huh?"

"Kind of," Xavier responded as he finished off the last of his bagel. "Did I make you uncomfortable or – "

Rory shook her head. "That's not it," she insisted. "Look, Xavier, I've really enjoyed the time we've spent together this week and I really had a nice time last night, but –"

"Oh, don't start that," Xavier said. "Now it's uncomfortable."

"I'm just not used to this," Rory continued. "I mean, I feel like I should feel sorry for not wanting it to mean more, but –" She laughed. "I'm making this really weird for you, aren't I?"

"A little," Xavier replied. "Did you want it to mean more?"

"No," Rory told him. "I mean, did you?"

"I don't want to hurt your feelings, but I thought we were –" Xavier shrugged.

"Just having fun," Rory finished for him.

"Exactly."

"I did," Rory said. "I just think in the long run, it should mean more. But at the same time, I don't regret it, either. And I'm still trying to work that out in my head."

"I get that," Xavier told her. "Really."

"I had the same boyfriend throughout most of college," Rory said, still attempting to explain herself. "I didn't really have the opportunity to figure this stuff out beforehand."

"You break up at graduation?" Xavier asked.

Rory nodded. "Pretty common story, right?"

"You could say that," Xavier responded. "Happened to me, too. She stayed in the area, actually, so she might be here tonight."

"Oh," Rory replied as a sudden realization hit her gut. Oh.

"Where's yours?" Xavier asked distractedly as he sipped his coffee.

"California," Rory said quickly. "Xavier, is it weird for us to be hooking up here?"

"You mean is it weird besides the fact that it's turned you off of the whole experience of casual sex completely?"

Rory let loose a nervous laugh. "No, Xavier, it's just that – well, being on your home turf and everything."

Xavier scoffed. "Oh, that. I don't discriminate when it comes to girlfriend material –"

Rory raised an eyebrow.

"Or to people I just want to have fun with," he continued. "Besides, you're cute and I liked hanging out with you this week. Why not give it a shot?"

Rory laughed. "So we're still friends?"

Xavier grinned. "Still friends."

The whole experience with Xavier seemed to break Rory out of her funk. She had watched an earlier debate in New Hampshire, and been underwhelmed, but as she watched the candidates interacting on the stage, she actually felt enlivened and energized by what she was witnessing, particularly with the drama surrounding the one candidate who openly castigated the people beside him on the stage for their supposed sins. She could feel a hidden drama lurking in the shadows, and although it certainly wasn't what she was there to write about, she wondered what she might find if she dug just a little deeper.

The investigative drive had been inspired in her, and she was actually looking forward to where it would lead next.

In the meantime, she and Xavier had kept their promises, and continued to share trade stories of prep school and college as they worked on their article together. He moved on romantically – if you wanted to call it that – within the next few days, and Rory expected to feel jealous, or guilty about the night that they shared, but the feeling never came.

She still didn't know what it all meant, other than the fact that she didn't want to repeat the experience. She was interested in what she was doing and began to feel for the first time in weeks that she actually had a purpose in being on the campaign trail. If it had taken an accidental one-night stand for her to get there, then the least she could do was to be grateful for it.

It took Lorelai a few phone conversations to needle the truth out of Rory, but she finally succeeded on the fourth try.

They had covered every conceivable topic that Lorelai would allow: Luke, the forthcoming visit with April (Lorelai was tentatively looking forward to it), Sookie's imminent delivery, the frequent baby-sitting she and Luke were doing for Lane and Liz, Kirk's attempts to get Luke to participate in the Fourth of July parade, and the fact that Luke was now attending every town meeting with Lorelai and Taylor was convinced that there was some sort of sinister reasoning behind it.

Rory talked about the Howard debate a little, but had precious little to tell her mothers on the events that had led to it: she had been so listless and confused the first few weeks she barely remembered anything that had happened.

The words slipped out before Rory could stop herself.

"How did you feel the first time you hooked up with someone for a one-time thing?

Lorelai stopped in her tracks and retreated from the kitchen where Luke was adroitly whipping up some lasagna and headed upstairs towards her bedroom.

"Rory, that's definitely a tidbit of information you've left out."

"I didn't –" Rory sighed and flopped down on her hotel room bed. "It happened right before the debate."

"Well, it's only a one-time thing if you agree not to see each other again," Lorelai said. "Do you want to see him again?"

"I don't," Rory said immediately. "At least not romantically. We both agreed on that. We're still friends. We wrote that article together. We still have breakfast together every other morning."

"And you're okay with that?" Lorelai asked, trying to suss out the situation.

"I am," Rory insisted. "I enjoyed it – during. And I didn't really regret it afterwards. I keep feeling like I should have, though. I just –"

"Rory, if that's the way you feel, then there's not any shame in that," Lorelai told her daughter. "As long as you parted on good terms and aren't interfering in anyone else's relationship."

"That's just it, though," Rory said. "I didn't feel anything. And I felt I should feel something. I figured there's some part of me that wanted to feel that thrill, you know. There's still romance in my head of traveling the world and having affairs in these far flung places and it just wasn't like that at all. There was no romance in it whatsoever."

"Rory, it's going to be rare that anything you experience in life is going to live up to what you've been building up in your head for years," Lorelai pointed out.

"But I've felt it before!" Rory said, a little bit louder than she had intended. "I felt that with Logan, when we first got together. It was different from that new relationship rush, because it wasn't a relationship, and maybe it turned into something ugly after a few months, but then it got better. And even if I liked it when it was better, I still felt that excitement at first. It wasn't there this time, and I was expecting it to be."

Lorelai remained silent, her heart twisting as she remembered Rory drunk and sobbing on the floor of her bathroom, crying that Logan didn't like her anymore. It was hard to weigh that memory against that of the earnest young man asking her for her daughter's hand in marriage.

And yet it had ended up in the same way, with Rory's heart broken once again. Lorelai was well aware of how much more it could hurt when that first-time rush transformed into a real relationship before everything fell to pieces.

That romance of knowing what it was like to start things over from the beginning didn't always hold up once you put yourself through it again.

"You're just a month removed from your relationship with Logan," Lorelai gently told her daughter. "I don't think anyone else is going to live up to him for quite a while."

"I wasn't expecting that," Rory replied. "But I was expecting – well, something. I just have to think now of what kind of relationship I can expect if I'm going to live this kind of life. I don't think I'm suited to hooking up with people like this, but I keep thinking of Logan and how he wasn't willing to continue this with me. I don't know who else is going to be willing to go along with it at this point."

"Rory, do you regret that you told Logan no?" Lorelai asked.

Rory sniffled. "No," she said honestly. "I needed to do this to find out what it was like, if nothing else. The reality hasn't quite been what I thought it would be, but I'm warming up to it. I think I was maybe a little too homesick at first."

"Then that's all you need to know," Lorelai said. "The fact that Logan wouldn't give you this space is on Logan, not you. You've got the rest of your life to figure out what kind of relationship is going to work for you."

"I guess you're right," Rory said, feeling a little bit reassured. "You never answered my question, though, Mom."

Lorelai sighed. "Rory, I never had a one-night stand."

"Really?" Rory asked incredulously.

"Thank you, dear daughter," Lorelai answered, rolling her eyes.

"I didn't mean –" Rory began.

"We lived in a potting shed until you were eleven years old," Lorelai said. "We slept in the same bed, Rory. How exactly was I going to manage this?"

"I know, but –" Rory paused. "Even back then, I used to stay with Mia or Sookie sometimes so that you could have 'grown-up time.' At least that's what Mia called it."

"That didn't happen often, Rory," Lorelai pointed out. "I know you were probably too little to remember it, but I would always be there by ten at the latest, and you'd just be on the verge of falling asleep. Mia or Sookie would drive us home and you wouldn't actually conk out until we were tucked into the same bed."

Rory smiled. "I do remember that, actually."

"I'm not saying that I never found someone I liked and was with them for a limited amount of time," Lorelai explained. "Call them three or four or five night stands if you want. It was all very structured and planned out in advance. When I was your age, I had a kid in kindergarten and a goal to move up from the front desk and a lot of rules about how close anyone was going to get to any of that. It didn't result in a lot of dates."

"I guess I never thought about it that way," Rory said in a small voice. "It's just – you always had your nights out and your time alone and I wasn't allowed to know about any of it. Maybe I remember more of it after we moved to the house."

"I started being more open to it once you were old enough to be left alone at night," Lorelai said. "But it still didn't happen that often. And I was always home by eleven. I wasn't going to let anyone else interfere with our life, Rory. I knew where we needed to be and what we needed to do to get there, and I wasn't going to let anything as insignificant as a boyfriend get in the way."

"I guess I made it into more than it was since it was the only thing you really kept secret," Rory mused.

"Well, if a side effect of that is that I appear to be more glamorous and in demand than I actually am, I'm willing to accept that," Lorelai said with a hint of arrogance in her voice. "The thing is, Rory, I'm not sure why this is coming up now. I thought you had your own version of this when you started dating Logan. Weren't you stringing one of his friends along for a while?"

"I wasn't," Rory clarified. "I was using his friend Robert for a while to make him jealous, but the most we ever did is make out a little." She sighed. "The end result was always getting Logan to myself. I don't think I ever even seriously considered hooking up with his friends."

"And now?" Lorelai prodded.

"I don't think I'll do it again," Rory affirmed. "It's not me. Maybe I needed to experience it once to find out that I didn't want it, but it's definitely not what I'm looking for."

"And you were protected –"

"That lesson was instilled in me a long time ago," Rory assured her mother. "I know how to take care of myself, Mom."

Lorelai breathed a slight sigh of relief. 'I'm glad," she said. "About all of it. I want you to do whatever makes you happy, Rory, but I'll tell you what I did before. This kind of thing really isn't for you. You're a relationship-oriented girl, Rory, and I want that for you. I want this to be easier on you than it was for me."

"How is that going, anyway?" Rory asked.

"We're getting there," Lorelai said, not wanting to divulge the details of what had been hashed out in therapy. "It's going to take time, but we both know what we want this time around. It's just going to take a little extra effort to get there."

"So I don't need to set any dates aside yet or –"

"Not yet," Lorelai clarified. "Rory, after what happened last year the last thing either Luke and I need is to rush this before we're ready. But when we are, we'll let both you and April know. Okay?"

Rory was a little surprised to hear her possible future stepsister's name dropped so easily, but she took it as a good sign. A very good sign.

"I want you to be good at this, too, Mom," Rory told her sincerely.

"Me, too, kid," Lorelai told her daughter. "Me too."

The day after her joint article with Xavier was posted, Rory received an e-mail that took her a little off guard.

Saw the article on the website this morning. Way to go, Gilmore! Drop me a text when you're in Philly and we can grab a coffee. It's been a while.

XO Jess Mariano

Rory grinned to herself, recalling how her relationship with Jess had miraculously been repaired in the wake of her near-infidelity last summer.

She had called him a few weeks later to apologize, feeling blindsided over what has transpired between her parents the night her mother broke it off with Luke and realizing immediately that she had almost done worse to the men in her life. She loved Logan, but she still cared for Jess and felt badly for how she had nearly used him. She had almost gone far enough to hurt them both out of spite, and she still regretted how close she had gotten to actually doing it.

Jess seemed to take her apology sincerely, but she wondered if he'd ever want to talk to her again, especially after the breakdown of her mother's relationship with Luke.

She had run into Jess in town shortly after her parents had gotten married. He had come into town to meet his newborn sister and seemed happy to see Rory. They went to get coffee at Weston's – Rory was still hesitant to step foot inside the diner often, especially given recent circumstances – and chatted about books and town gossip. Jess told her about some of the books the press was putting out and Rory talked about her plans for the future. Jess asked if she'd consider working at the Philadelphia Inquirer if she didn't end up in New York, and Rory said she would think about it.

Any remaining awkwardness between them seemed to have completely disappeared. That may have been because they avoided the subject of Luke and Lorelai, but Rory liked to think it was because they were capable of being friends now without being angry or bitter about the past. Since then, they'd kept in touch with each other by occasional text or e-mail, and Rory had been planning to look him up when the campaign traveled to his city even before he had mentioned it.

Despite their own rocky personal history, Jess had known and respected her long before she was the girl that Logan or that Yale knew, or the girl just beginning to make her way on the campaign trail. It felt good to be in touch with someone who had some idea of who she was at her core.

The rest would take a while to figure out.