Author's Note:

To address a couple of reviews: First, I am aware that Rory and Dean were together 3 times, not just two, but I felt that the first two times they were together, the characters were substantially the same. Thus had Rory stayed with Dean the first time or the second time, What Might Have Been would likely have been the exact same place.

Thus since she and Tristan were never actually together, I have his bit set after Dean the first time, but before Jess.

As to Jess, because his return in season 4 was for two minutes just asking her to go away with him, it does not get it's own chapter. (Also, I have no idea how Jess changed between leaving for California and coming to see Rory at Yale) Jess II is written as if Jess and Rory got together in Season 6.

Rory Gilmore stood in front of her full-length mirror, applying her lipstick, and getting ready to go on yet another interview.

"Jess, have you seen my Birkin Bag?"

"Your what bag?" he asked.

"My Birkin Bag, it's my hot pink shoulder bag," she explained.

"I can't believe you name your bags," he said with a sigh, "but I think it's on the couch."

"I didn't name the bag, that's just the brand of the bag."

Jess rolled his eyes, "I can't believe you've become one of those people."

"What people?" she asked.

"Those 'my Coach sunglasses don't match my Fendi purse,' people," he explained in a faked posh voice.

"People with a sense of style?"

"No! The overly label conscious."

"Right," she said with a snort. "Can you find my other Christian Louboutin shoe?" She added fuel to his fire and held up a high heel.

Jess shot her a dark look.

"Please? I'm in a hurry." She bent down and began to dig for the shoe in the hall closet.

"Alright I'll check the bedroom," he said. A minute later he called out to her "I found it!"

"Thank you!" she exclaimed. "Where was it?"

"Next to your Old Navy flip flop," he told her with a smile as he handed her the shoe. He kissed her cheek.

"I wonder how my shoes got separated," she said absently.

"I don't know, but I think we need to get a bigger place." Jess had moved into a one bedroom apartment when he and Rory got back together. Living with 3 other guys was not conducive to weekend visits from his girlfriend. After she graduated she moved in with him in Philadelphia and she'd looking for a job ever since, and the two of them had been cramped in a tiny one bedroom apartment.

"As soon as I get a job," she agreed.

"Have fun stormin' the castle," he told her. It had become their way of tell each other good luck without the jinx of actually saying the words.

"You too," she said knowing he had two potential client meetings at Truncheon. She slipped on her heels, grabbed her Birkin bag and walked out the door.

The Philadelphia Inquirer was the fifth major paper that Rory had interviewed with. She'd resolutely avoided any of the Huntzberger-owned papers, but if she didn't get this job she might be forced to apply at one.

She walked into the lobby of the paper projecting an air of confidence that she didn't actually feel. "Yes, Rory Gilmore to see Tom Spaulding," she told the receptionist.

"Go ahead and have a seat Ms. Gilmore, Mr. Spaulding is just finishing up a meeting and will be with you in a moment."

Rory nodded in understanding and took a seat in one of hard leather chairs nearest the editor's door. She pulled out her portfolio, flipping through it one last time, and then made a few notes about questions to ask during the interview process. She heard the door open next to her and finished writing her sentence before she looked up.

"Rory?" She heard a familiar voice, but she couldn't quite place it.

"Yes?" she said in return finally looking up into the eyes of Mitchum Huntzberger. "Mitchum, hi."

"What are you doing here?" he asked.

Rory noticed he was standing next to a man that was in all likelihood the editor she was about to interview with. "I'm here for an interview," she told him as politely as possible. She really wanted to ask him why it mattered, but didn't want to appear rude to him in front of this editor. "What are you doing here?"

"Just checking things out," he answered vaguely. He turned to the man standing next to him, "Well I'd better get going Tom, I'll call you back later in the week, and maybe we can work out some details." The man nodded. "Rory, it was nice to see you. Give my regards to Richard and Emily."

She tried not to look incredulous as she nodded at his request. "Give my regards to your family as well." She glanced over at Tom and watched his face as Mitchum walked away. She swore she could smell sulfur, but knew better than to ask him if he could smell it as well.

It took a minute or so for Tom to pull himself back together and remember that Rory was there. While Rory waited patiently she thought about What Might Have Been, had she and Logan stayed together she'd likely already have a job, with no one wanting to upset the Huntzberger heir and all, but she knew she'd rather do it on her own, even if she was so tired of interviewing the mere thought of it made her head hurt.

"I'm sorry," Tom said suddenly. "Are you Ms. Gilmore?"

"Yes. Hi. Rory Gilmore. It's a pleasure to meet you," she said as she stuck out her hand to shake his.

"Come on into my office," he told her when he dropped her hand. He turned and walked towards the office with her following close on his heels. "So, how do you know Mitchum Huntzberger?"

"Wow, you really cut right to the chase don't you," Rory said flippantly, taken a little aback at the blunt question. She waited a beat for him to explain or withdraw the question, but he just continued to stare at her. "I went to Yale, and I interned at the Stamford Eagle Gazette with him." She hoped that answer was satisfactory, she really didn't want to talk about Logan right now.

"Oh. And you know his family?" Tom asked.

"Yes, but I'm not sure how that's relevant," she responded.

Tom shook his head as though he were clearing away dusty thoughts. "You're right it's not at all relevant. Why don't you have a seat, while I look through your portfolio again," he said.

"Thank you," she replied taking a seat across from his desk, and watching with interest as he flipped through her portfolio. He smiled occasionally as he read something that interested him, and she curiously wondered which article it was.

"You have a very impressive portfolio Ms. Gilmore. So what brings you down to Philadelphia?"

"My boyfriend," she said politely. "He's one of the owners of a small independent publishing house," she paused for a moment trying to determine whether to continue. Tom smiled encouragingly and she pressed on, "Truncheon Books."

"Why do you think you'd be an asset to the Inquirer?"

"I have a lot of experience writing… is Huntzberger Publishing Group interested in acquiring the Inquirer?" she asked out of nowhere. She knew it wasn't any of her business, but she couldn't help but ask just the same.

"Well…" Tom started slowly, likely weighing exactly what he should or could say. "I honestly don't know. Does that matter to you?"

She shrugged, trying to determine if it really did matter to her. "I guess not. I think I'd just like to know in advance if I would be working with Mitchum again."

"Well you seem to be in a better place to know that than I do," Tom told her. She looked at him curiously, obviously confused by his statement. "Well you are on a first name basis with him."

Again she shrugged, then redirected the conversation to where it was before she interrupted herself. "As I was saying, I've written a lot, I was a staff writer for the Yale Daily News for 2 years before I became the editor in chief. I also did some writing for the Stamford Eagle Gazette."

"What kind of writing are you looking to do here?" he asked.

"I really like to do all of it. Features, news, reviews, heck once I even wrote a piece on the repaving of a parking lot," she explained with a smile.

"Do you have a problem traveling?"

"No, in fact, I quite enjoy it."

"Do you have any questions for me?"

"Do you know when you expect to make a decision on the position?" she asked, surprised at her own forwardness.

"I have a few more candidates to interview, and I intend to have a decision made by the end of the week."

"Okay."

"Anything else?" he asked.

"I don't think so, thank you," she replied.

"It was a pleasure meeting you Ms. Gilmore, I'm sure I'll be speaking to you in the near future." He stood up, smiled at her and extended his hand for her to shake it.

She stood up and shook his hand, "thank you for your time Mr. Spaulding."

Her drive back to their apartment took an inordinate amount of time, thanks to a traffic accident that blocked three lanes of the road, and by the time she got home she had convinced herself that she'd never get the job at the Inquirer and it was all Mitchum's fault.

She let herself into the apartment and headed straight for the freezer. The only thing that could make her day better right now was a carton of Phish Food and great news from Jess about his day.

She was on the couch about two-thirds of the way through the carton when she heard the key click in the lock. "Hey babe," she called to him.

"Hey," he replied sullenly. "How did the interview go?"

"Nope. You first. How did your client interviews go?" She fervently hoped for good news, she needed something to celebrate.

He grabbed her Birkin Bag off the couch and threw it across the room angrily, then plopped down on the couch next to her. "Not good."

"I'm sorry, but that doesn't mean you need to throw ten thousand dollars worth of handbag across the room."

He looked at her incredulously, then at the handbag, then back at her. "Why the hell do you have a $10,000.00 purse?"

"It was a gift," she told him.

"That thing could pay our rent for 6 months!" he yelled.

"Why are you yelling? It's not like I paid ten grand for the bag."

"I can't afford to buy you a bag like that," he said weakly.

"So what? I didn't ask you to buy me a bag like that. Hell I didn't ask for this bag in the first place."

He nodded, accepting her answer for the moment. "So how was your interview?"

"Ran into Mitchum Huntzberger," she told him nonchalantly, not wanting to keep it from him, but not wanting him to overreact either.

Jess shoved his hands through his hair and sighed deeply. "Who are you?"

"Jess," she started nervously, "what are you talking about?"

"You wear designer shoes, carry a $10,000 purse and are on a first name basis with one of the worlds largest newspaper moguls."

"I'm still Rory. I can't change my past. You know that. You can't change yours either."

"I can't give you that life."

"I didn't ask you for it."

Jess stood up and began to pace the living room. Rory watched as he walked, wondering what his next move would be. He finally walked over to the door and grabbed his jacket.

"Jess, where are you going?" she asked.

"I need to think." He stormed out the door, slamming it behind him, and Rory began to think too.

AN: Alright, all the things I don't own: Gilmore Girls, Coach, Fendi, Christian Louboutin shoes, a Birkin Bag, The Princess Bride, or Ben and Jerry's.

Thoughts behind this bit: I think that Rory, post Logan the first time, learned a bit about how the other side lives. And while I don't think she'd become a total snob, I think that she probably learned to appreciate a few of the finer things in life.

Let me know what you think!

Up Next: Logan II

Then an epilogue as per requested… I just don't know how it'll turn out yet.

So I guess a poll: If Rory got back together with any of her exes – post season 7 – who would you like to see, and why?

Please read and review - S