AN: A new story from me! I'm not sure how often I'll update, but I got this plot bunny stuck in my head and I can't get rid of it, so here it goes.

Setting: 10 years after the series finale. Yes, this is a future fic, with lots of flashbacks.

Title Note: This is named after one of my favorite Paul Westerberg songs. You should listen to it if you haven't heard it.

Disclaimer: As usual, I don't own anything.

"I'm sorry the news isn't better Ms. Gilmore," the kindly voice on the other end of the phone told her apologetically.

"And you're sure?" she asked.

"Yes ma'am, I'm sorry."

"Thank you for letting me know," Rory said with as much politeness as she could muster.

"Have a nice day."

She resisted the urge to snort, as if a nice day was possible now. "You too." She hung up the phone and chuckled bitterly. Life was filled with irony, she knew that. She just didn't like it when she was the subject of it.

Rory looked down at the to-do list on her desk and decided that there was nothing that couldn't wait. Her latest article was already set for printing but wasn't due to run for another few days, and the one after that was currently sitting on her editor's desk for review.

She turned off her monitor, pulled her coat on, and grabbed her bag. As she left her office she paused at her assistant's desk, "Amanda, I'm headed out for the rest of the day." It was only 10 am.

"Alright Rory, are you okay?"

She bit the inside of her lip to prevent herself from crying. "Yes, I'm fine," she lied.

"So if Art calls?"

"He shouldn't, but if he does tell him to call my mobile." Art was her editor, a grandfatherly little man, who was a killer editor even if he let his staff call most of the shots. More than likely he'd only call her for a scoop.

"Okay. See you tomorrow," Amanda called as Rory headed towards the elevator.

Rory nodded and continued on her way, wondering to herself if she'd actually make it into the office any time soon again.

She drove straight home, which was odd for her, because usually the trip required at least one drive through espresso stand, but today she just couldn't be bothered. As she pulled her BMW into the driveway, she hit the button on the visor to open the garage door. She pulled the car into the garage and was silently thankful that he wasn't home. That would hopefully make things… easier.

Rory got out of the car and headed into the house, but instead of her usual routine, she headed straight for the guest room to pull out her suitcase. She pulled it down the hall into the master bedroom, but instead of laying it on the bed to start packing, she left it, and flopped on the bed herself. She could afford a few minutes to wallow.

As she thought about the situation, she began to chuckle that bitter chuckle again. Her ex-husband would just love the irony of this. Her mind wandered back to the beginning…

Ten Years Earlier

As a fresh-faced college graduate, Rory boarded the press bus with the rest of the Obama press corps. This was just what she needed. Hopefully this would keep her busy so she wouldn't have time to miss Logan. Turning him down was the right thing to do, even if it hurt like hell.

The first month she felt sorry for her roommates. During the days she was busy enough to forget, trying to get the hang of things and trying to keep the pace of writing new articles every few days about the speech she'd heard many times. The nights were a different story. She was prone to late night crying jags and equally late night conversations with her mother. She lucked out that most of the people she was assigned to room with were sympathetic to her situation.

After the first month she started to move on, she became acclimated to the pace, and learned to retell the same story in a different light, she stopped waking up in tears in the middle of the night, and she started calling her mother at more reasonable times. The only downside was now, she had more time during the day to think about what she wanted with her life.

She sat on the bus watching the cornfields go by as she thought about where she wanted to go, and who she wanted to be. She knew she still wanted to write, but she wasn't completely certain she still wanted to be a foreign correspondent. She thought about her past loves and her future dreams. She knew exactly how her life would have turned out had she stayed with Dean. They would have stayed in Stars Hollow. She would have worked at the Stars Hollow Gazette, or maybe the Hartford Courant if she felt up to a commute. They would have had a couple of kids, and the biggest adventure she'd have would be the occasional weekend trip to New York or Boston. It would have been a life full of Small Town Saturday Nights.

She was equally certain how her life would have turned out had she said yes to Logan. They would have grand adventures. She could work anywhere and they would travel whenever. But on the other side, they'd be under constant scrutiny, both from the media, and the Hartford Society. She knew that no matter how much Logan professed that he was done with his father and Huntzberger Publishing Group, eventually he would return. Whether he liked it or not, the newspaper business was in his blood, and he was damn good at it, and in the end he could never completely ignore his family obligations. They too would have children, but instead of having kids, they'd be producing heirs.

Jess was the wild card. Try as she might, Rory couldn't see how her life would have turned out with Jess. Maybe it was because their moments of happiness were fleeting. Or maybe it was because Jess had changed so much over the course of the years there wasn't enough data to extrapolate from. Either way, her curiosity was peaked. She wouldn't go as far as saying that Jess was 'the one that got away', but she also couldn't say that he wasn't. There were so many moments she wished she could go back and change. What if her arm hadn't been broken that night, causing Jess to leave town? What if he'd said one word on any of his many phone calls after he left? What if she'd said 'yes' when he came to take her away after her freshman year at Yale? What if she and Logan never got back together and she was single when she visited him at Truncheon? So many questions, and so few answers - truly a reporter's nightmare.

As the summer passed, Rory became herself again. Things that reminded her of Logan still stung a bit, but they no longer threatened to bring her to tears. She got to know her coworkers, and she actually managed a few first dates. None of them were worth writing home about, but she felt like she was making progress.

In October, the tour stopped in Philadelphia. She thought about calling Jess, but decided that he was probably still mad at her after she showed up to his grand opening and tried to use him to cheat on Logan. She was surprised to find him leaning up against the wall in the back of the building where the press conference was held. She packed up her stuff and made her way towards him.

"What are you doing here?" she asked.

"I'm happy to see you too Rory," he shot back sarcastically.

"Oh! No! I'm happy to see you, I'm just surprised. After last time…" she trailed off.

Jess merely shrugged in response.

"So what are you doing here?" she asked again.

"I came to see you. You wanna get a drink and catch up?"

"Sure."

And just like that, she and Jess were okay. She followed him out of the building and down the street into a small pub. They talked for hours, catching up on each others lives and the Stars Hollow gossip.

"How long are you in town?" Jess asked as she climbed out of the cab at her hotel.

"What day is today?" she asked. He gave her a funny look. "What? Working every day and traveling all the time screws with my mental calendar."

"It's Monday." He stepped out of the cab with her but left the door open so he could get back in it.

"Okay, we're leaving Wednesday morning."

"Dinner tomorrow night?"

"I'd like that." She smiled at him.

"Meet me at Truncheon at 7:00 then," he instructed. She nodded, and he leaned in and kissed her cheek.

"Night," she called.

He climbed back into the cab, and waved from the back seat.

The next night they met for dinner, which was followed by late night coffee, which was subsequently followed by breakfast on Wednesday morning before she had to get back to her hotel and board the bus.

"I'll call you," Jess told her as he kissed her goodbye outside her hotel.

"I'd like that."

She didn't expect him to call. In fact she didn't expect to ever see him again. But having finally slept with Jess Mariano, she felt a sense of satisfaction. An itch that had finally been scratched.

But Jess did call. At first it was maybe once a week. Then it graduated to a weekly phone call, plus some emails. Then to daily phone calls and emails. Then to nightly phone calls and copious texting throughout the day.

By the time the campaign trail ended, Rory talked to Jess more than anyone else. And so, when she was looking for jobs, she applied to a couple of papers in Philadelphia, was well as to several other places.

When she was offered a position in Philly on the political beat, she called Jess, and they talked it over. It was a good offer, and it wasn't like she would be taking it just for Jess. But they thought it would be fun to be in the same city.

She accepted the position, and just as she was moving to Philly, Jess's roommate moved out, leaving him with an extra bedroom. So Rory moved in.

When she moved in, it wasn't like they were a couple. Their one night during the campaign hadn't left either one of them with delusions of a relationship. But, the close proximity soon changed their status. Over the course of about 18 months, they went from friends, to friends with benefits, to boyfriend/girlfriend, to engaged-to-be-married, to newlyweds.

While their personal relationship progressed, so did their careers. Rory was a rising star at the Philadelphia Observer, and Truncheon was growing by leaps and bounds. About six months after they married, Rory got her first chance to be a Foreign Correspondent. A three-week assignment in Iraq. This also coincided with their first real argument.

"Wow, that was amazing," Rory panted.

"You're telling me," Jess said, equally out of breath, as he sprawled across their bed. "I can't believe you're willing to go three weeks without this."

"At least I'm doing it now, before we have kids," she shot back with a smile.

Jess's face locked up.

"What?" she asked.

They'd never had a conversation about kids. At this point, work had kept them both too busy to think about anything other than the immediate future. Jess had never expressed an opinion either way, and Rory knew that if she did want kids, it wouldn't be for a long time.

"I'm not having kids," Jess told her.

"Well not right now. That wouldn't make sense at all," she agreed.

"No. I'm not having kids ever."

"How can you be so sure? With the exception of you, I hardly know what I want next week, let alone for the rest of my life."

"I had a vasectomy when I was 20," he told her flatly.

"And you didn't feel I needed to know that?" she asked incredulously.

"It never came up."

"Why?"

"Why didn't it come up?" he asked.

"No, why did you do it so young?" she asked.

"I had a scare with a girl I was dating, and decided I never wanted to go through that again."

"But…" Rory wanted more information.

"Look at my parents Rory. I would never want to do that to a kid," he started.

"You're not Liz or Jimmy," Rory reminded him. Even though Liz and TJ had been married for years, and hadn't yet screwed up Doula, and Jimmy and Sasha were still going strong, Rory knew that Jess still couldn't get past his own screwed up childhood. She didn't expect him to.

He shrugged. "You never made any mention of wanting to have kids, so I just figured you felt the same way I did."

"Hey!" Rory started, ready to defend her parents, "I know my childhood wasn't ideal, but that didn't put me off kids forever."

"I'm sorry I didn't tell you."

Rory remained silent, trying to process the information that she'd never be a mother.

After a few minutes passed Jess spoke again, "Rory, say something. Please?"

"You mean to tell me we've been wasting money on birth control for the past two years?" she finally said, trying to lighten the situation. She wasn't over it, but she didn't want to spend their last few hours together fighting.

Jess chuckled. "Sorry."

Time passed, and Rory spent more and more time overseas. While she wasn't 100 percent happy with the fact that she and Jess were never going to have kids, she managed to put it out of her mind. She was enjoying her job too much to be too upset.

She was 28 before she felt her biological clock start to tick. Before then she'd heard the occasional tick when she attended baby showers or held her baby brother and sister, knowing she'd never have that. But nothing she couldn't rationalize away. She was still spending about half of every month on the road, so she wasn't at a point where she wanted to try to convince Jess to have his vasectomy reversed. She wasn't 100 percent sure she wanted kids herself, but she thought she might. In the end it didn't matter, that wasn't what drove her and Jess apart.

Her most recent trip had taken her to Paris for two weeks, and for some reason she found herself really missing her husband. They'd had an argument before she left about her being gone for their wedding anniversary. This was the first time that she'd had to miss it due to work. So she decided to make arrangements to get home a day early to surprise him.

When she arrived at Truncheon, straight from the airport, she headed right for his office. Over the years Truncheon had grown into a bigger publishing house, but Jess and his partners had refused to part with their original space. They still had their offices there, and held meetings there. Rory walked past the empty desk that usually was occupied by Janice, Jess's secretary and headed to his office.

She paused outside the door to find out if he was in a meeting.

"How about tomorrow?" she heard a feminine voice say.

"Sorry I can't, my wife is due back in town," Jess told her. Rory decided the meeting must have been about over and it would be okay to interrupt.

She opened to door to find a young blonde, probably 24, zipping her skirt and slipping into her shoes, and she glanced over to see Jess pulling his tee shirt over his head, and tucking it into his unbuttoned jeans. Oddly as she took in the situation, the thing that stood out to her was how little Jess had changed since they were 24. He still spent 95 percent of his time in jeans and tee shirts. The only concession he made was that now the jeans weren't riddled with holes and the tee shirts lacked curse words.

"Janice, I told you not to interrupt my meetings with potential authors," he said without looking at the door.

"Sorry, I didn't know," Rory replied.

Jess froze at the sound of her voice. "Rory?"

"I came home early. I didn't want to miss our anniversary." She turned on her heel and headed back towards the front door, luggage in tow.

"Rory wait!" Jess called.

She stormed out of the building and hailed a cab. Jess was in the cab right behind her, getting home just moments after her.

"Let me explain," he started.

"You're seeing someone else, what is there to explain? What I saw is pretty much self explanatory."

"It was just that once… and I was just so upset about you missing our anniversary," he tried to explain.

"That's great Jess. Since I couldn't be here you decided to spend our anniversary fucking someone else? That makes me feel so much better."

She headed up the stairs of their town house to the bedroom. Jess chased her up the stairs.

"Please don't leave… I'm so sorry."

"Get out of my way."

"It was only that one time!"

"I don't care."

That was it. She moved into a hotel and started applying for jobs in other places. She wanted to go home, so she applied mainly in Connecticut, New York, and Massachusetts. Given her cv and her portfolio, it didn't take long for her to get another job, and soon she was in New York, starting over.

Rory didn't think about her marriage to Jess too often. While they hadn't parted in an amiable manner, her mom and Luke had finally gotten married around the same time they had, so eventually they had to at least get back to being civil to each other.

As she sat on the edge of her bed drying her eyes she wondered, had Jess never cheated, would they still be together? Or would the desire to have children finally gotten the better of her and caused her to leave anyhow?

"Get yourself together, Gilmore!" she scolded herself aloud. She stood up and pulled her wheeled suitcase up onto the bed. She unzipped it, and finally set about her original task, packing.

It took her less than 30 minutes to pack enough stuff to stay gone for a week. She could always buy more, and she knew eventually, she'd have to come back for the rest.

She tugged the suitcase down the hall, and paused at her office. She went in and grabbed a piece of paper. He at least deserved a note. Instead of sitting at her desk to write it, she took it to the kitchen, she wanted to leave it somewhere she knew he'd find it.

She sat down on a bar stool in their kitchen and started writing her note. Tears dripped down her face as she wrote, leaving the ink smeary, and the paper oddly bumpy from the patches that gotten wet, then dried. She wrote for a few minutes, and finally got to the bottom of the page. She signed the note, and hugged it to her chest briefly, further crinkling the paper, before setting it back down on the counter. She knew she should leave her wedding ring with the note, but she just couldn't do it. She looked down at her hand, and she just couldn't bring herself to remove the ring.

Rory towed her suitcase to the garage, and loaded into the trunk of her car. She backed out of her garage and watched as the garage door slowly closed behind her. She wiped her eyes again, put on some sunglasses, and pointed the car to the north.

Double duty for the author's note, sorry about that. Well, what do you think? Do you love it? Do you hate it? Is it overly predictable? Should I keep going?

Also, I wanted to say thanks to Miguel51 for taking the time to read this in advance, and encourage me to post. I really appreciate it.

Please read and review! Reviews make the muse write... who knew.

Thanks for reading

S