Rory turned away from the sunlight streaming into her bedroom, a smile plastered to her face. Though she tried to get back to sleep, it was no use. All she could think about was Jess. While they hadn't gone as far as she would have liked, the previous night had been amazing - she'd never felt so connected to anyone before.

After ten minutes of tossing and turning, she finally got out of bed and padded over to the mirror. She didn't look any different, but she felt it. For the first time in a long time, she felt at peace. Subsequently she took a shower and dressed, then she went downstairs to the kitchen where she found her mother standing at the kitchen sink rinsing out a coffee mug and humming "Girls Just Wanna Have Fun."

"Hey," Rory said as she made a beeline for the cabinets above Lorelei's head. Even though she was already wired, she still craved her coffee.

Lorelei turned, giving her a smile, "Sleep well last night?"

"Wonderfully," Rory said as she spun around the kitchen like a ballerina. She knew she looked silly but she couldn't help it.

"Why are you so happy?"

"No reason."

"Uh huh. So I guess you wouldn't be interested in going to Luke's for coffee."

"On the contrary."

After grabbing their jackets and bags, Rory and Lorelei headed outside. The brightness of the sun blinded Rory as she and her mom made their way down the street. The air outside was cool and comfortable. Everything looked green, vibrant, alive. So much so that she couldn't help smiling at everyone she met. As they made their way across the town square, her heart began pounding furiously – anticipation and excitement at the thought of seeing Jess.

"Hey Taylor," she said as she and Lorelei passed Doose's Market.

The second they were out of earshot, Lorelei turned to her wide-eyed and said, "Oh my god, you're high, aren't you? Answer me, damn you! Because whatever it is, it must be primo stuff."

Rory smiled without saying a word as they continued on to Luke's. Upon entering the diner, she saw him standing behind the counter pacing, muttering to himself. Quickly she scanned the place looking for Jess, but he was nowhere to be seen. He must be upstairs.

"Hey Luke," Lorelei said walking up to the counter and sitting down.

"Oh hi Lorelei," he said distractedly.

"Something wrong?"

"It's Jess; he's gone."

"What," Rory said, stopping where she stood, glued to the floor.

"He left last night to go stay with his dad in California."

Suddenly she felt nauseous and unable to breathe. Jess was gone and he hadn't even bothered to say goodbye.

"I … I," she began.

"Rory, are you okay?" Lorelei asked standing up.

"No," she said then bolted from the diner. She ran - across the square, past Kirk, past Miss Patty, past Babette - until she reached a clump of bushes where she instantly threw up.

xxxxxxxxxxxx

Ten Years Later

"Don't forget your two o'clock with Anthony Bourdain," Andrea Swan said as she and Rory made their way to latter's office.

"I won't. And Andrea, Wednesday I'm having lunch with Gore Vidal. Please put that on my calendar. Thanks."

"No problem," Andrea said as she tried keeping up with her boss. Andrea Swan had been her assistant for a little over a year and Rory liked her. She was smart, hardworking, dependable, and easy to get along with. She was pretty too though one wouldn't notice it straight away because of her long blonde hair pulled back in a severe ponytail and her blue eyes hidden behind horn-rimmed glasses. "Your grandmother called," Andrea continued. "She wants to confirm Friday dinner. Also, here's that manuscript Tom wants you to edit."

"What's the book about?" Rory asked. Her boss Tom Ferguson had been badgering her for weeks about a hot new manuscript he wanted her to read. She hadn't wanted to do it so she hadn't asked too many questions about it. "It's a modern On the Road. Apparently, the guy who wrote it has lived all over the world – Thailand, Kenya, Central America, you name it. He's written a book about his travels," Andrea said handing Rory the pages.

"Thanks," she said as she stepped into her office, closing the door behind her.

This was not the life she'd imagined for herself. Working at Simon & Schuster was fine. She liked guiding new writers, helping them develop their talent but she'd dreamed of being the next Christiane Amanpour, reporting from hotspots around the world – Afghanistan, the Middle East, Africa. But after a year of traveling with the Obama campaign, she'd accepted an editorial assistant position at Random House, then she'd been promoted to assistant editor, and now she was an editor at Simon & Schuster. What happened? How had her dreams just slipped away?

She picked up the manuscript Andrea had given her and grabbing her cup of coffee, leaned back in her chair and began reading it.

Four hours later, she was so caught up in a story about aboriginal tribes in the Amazon Rainforest that she hadn't heard Andrea knocking at the door.

"Rory," her assistant said hesitantly.

"Yes," she said looking up.

"You need to leave now if you want to make it on time to your two o'clock with Anthony Bourdain."

"Thanks," Rory said then began gathering her things. "I lost track of the time."

"The manuscript?"

"Uh huh."

"It's absolutely exciting, isn't it? I sneaked a peak. I hope you don't mind."

"Not at all."

"I wonder what he looks like, the guy who wrote it," Andrea said dreamily. "I bet he's handsome and rugged. You know, like Gerard Butler."

Rory had been wondering the same thing. This guy sounded exciting. Plus, he was living the life she'd dreamed of and then some. Still … a life like that couldn't be conducive to a relationship.

"See you in two hours."

"Thanks."

xxxxxxxxxxxx

After lunch in the taxi on the way back to work, Rory pulled out the text again. She definitely wanted to give this author a call. He had a way with words and had seen so much. As she dug in her bag for her cell phone, she flipped to the first page of the document.

Her heart stopped.

It can't be, she thought as she dropped her phone back into her bag.

The second the cab stopped in front of her office, Rory hopped out and rushed into the building. Once safely ensconced in her office, she took a deep breath. With a trembling hand, she dialed the telephone number written on the manuscript and waited. The phone rang once, twice, finally on the third ring someone picked up.

"Hello?" a male voice said on the other end of the line.

Oh my god, it's him. Panicking, she almost dropped the phone.

"Hello?" he said again. "Hello?"

"Hello. My name is Rory Gilmore; may I speak with Jess Mariano please?"

"Rory Gilmore?" he asked bewildered.

"Yes. I'm an editor at Simon & Schuster. I'm calling about his manuscript Life Lessons, Life Travels.

"This is Jess Mariano."

"Hello Mr. Mariano," she said then cleared her throat. "Tom Ferguson from our office gave me your manuscript. We're really excited about it; you have some amazing stories here."

"Thanks."

"I was hoping we could meet for lunch to talk about it."

"That sounds great."

"Wonderful. How about tomorrow at the Gramercy Tavern? One o'clock?"

"Sure."

"Great. I'll see you then Mr. Mariano. Goodbye."

"Bye."

Quickly she hung up the phone. Though she was sitting down, she felt weak in the knees. What had she just done?

xxxxxxxxxxxxx

Sitting at a table in the middle of the restaurant Rory fidgeted as she kept glancing toward the door. The Gramercy Tavern was crowded as usual. With its walls lined with Robert Kushner murals and plush, thick carpeting, it was becoming more than just another New York restaurant but an institution.

She'd arrived early for two reasons: 1. It was in her nature to be on time and 2. She wanted to see him first so that she could prepare herself. For what she didn't know.

A flood of questions engulfed her. What did he look like now? Was he married? Did he have children? Did he ever think about her? Silly girl, she chided herself at that last thought.

Upon glancing at the door for the umpteenth time, she suddenly found herself unable to breathe.

He looked older. His hair was slightly longer and his face was peppered with scruff, but it was him. She watched transfixed as he boldly strode up to the maitre d'. A few seconds later, they both maneuvered their way to where she sat … waiting.

"Rory?" Jess said staring at her in disbelief. "It is you."

For a second her mind went blank, so lost was she in the wholeness of him. But just as quickly she snapped out of it. "Jess," she said extending her hand. He took it, shaking it as he sat down across the table from her.

Minutes passed without either saying a word. Unable to stand it any longer, Rory cleared her throat.

"As I mentioned over the phone, Tom Ferguson, one of our senior editors, has been raving about your manuscript for weeks."

"What did you think of it?" he asked, his eyes boring into her.

"I loved it," she said blushing, the intensity of his stare too much for her to bear.

"Good," he said looking away. He picked up a menu and began looking it over.

After they'd ordered, she sat back in her chair and smiled to herself. It was juvenile, but she couldn't help being pleased that Jess was pleased that she'd liked his manuscript. "So," she said breaking the silence that had crept up between them again.

"So," Jess repeated smiling at her. "What have you been up?"

"Nothing much."

"I find that hard to believe."

"Well," she said gathering her thoughts. "After graduating from Yale, I spent a year covering the Obama campaign. I worked at Random House for a few years and now I'm an editor at Simon & Schuster."

"I see," he said then took a swig of his scotch.

"See what?" she asked uneasily. Out of all the guys she'd ever dated, Jess was the one who seemed to have the uncanny ability to see through to her core.

"Nothing," he said shaking his head. "How's Lorelei?"

"She's fine. A few years ago, Town & Country did a write-up on the Dragonfly and it's been doing amazing business ever since."

"Ummmm. So, are you seeing someone?"

She sputtered, almost choking on the water she'd been drinking. Thankfully, it hadn't shot out of her mouth and onto her clothes. "Excuse me?" she said coughing.

"I asked if you were seeing someone," he said a mischievous grin on his face.

Rory didn't know why she was acting like this. Of course, inevitably, the question would have come up. And it was a simple straightforward question. Are you seeing someone? Are. You. Seeing. Someone?

"Why don't we talk about your manuscript? Everyone loves it. But …." She flushed crimson knowing how contradictory what she was about to say would sound. "Tom Ferguson would like you to rewrite the passages on the genocide in Africa. He fears they may be too graphic for a mass audience."

"Absolutely not."

"What."

"I'm not rewriting those pages. The victims of those atrocities deserve to have the truth told. You can't whitewash something like that."

Rory shifted in her chair. Of course he was right, but Tom wouldn't like it. The truth wasn't always an easy sell. She sighed. "I'll talk to him."

"Thanks," Jess said leaning back in his chair, staring at her silently again.

"What?" she said a little unhinged.

"Are you happy?"

"Am I happy?"

"Yes, it's a simple question."

She scoffed. There was nothing simple about it at all. People drove themselves mad in pursuit of happiness. "Why do you ask?"

"I need to know."

"Why? We haven't seen or talked to each other in ten years Jess. Why do you give a damn if I'm happy?"

"Because I still care about you. There hasn't been a day that I haven't thought about you."

"I find that hard to believe. Don't forget, I read your manuscript and you go into quite a bit of detail about a certain bargirl, Mandy is it, in Thailand."

It was Jess's turn to turn red but he kept his composure. "That's neither here nor there. I hate to see you so unhappy."

"What are you talking about? I am happy," Rory said emphatically. "My career is on track. Logan and I just bought a brownstone in Tribeca."

"Logan!"

"Yes, you met him that one time you came home for a visit."

"I remember him," Jess said, his body stiffening, his jaw tight. "I remember he was an asshole."

"Jess!"

"Seriously. How can you still be with that guy? Is he the reason you're not a reporter like you'd dreamed."

"I was a reporter; editing was a natural progression."

"You were going to see the world."

"I have seen the world. Logan and I …."

He cut her off.

"Logan and I," he mimicked, "have seen what? London, Paris, Cabo, Africa on safari. I'm talking about the real world, not what they show you in the travel brochures."

"I don't have to justify my life to you Jess," Rory said gathering her things.

"No you don't," he said quietly. "It's just that your life makes me sad."

Rory froze. Sad! He thought her life was sad. She stood without saying another word and walked out of the restaurant.

xxxxxxxxxxxxxxxxx

As she sat in the backseat of the taxi on the way home, Rory couldn't help replaying the conversation she'd had with Jess. She had a good life. Simon & Schuster was a decent place to work and Logan's company was doing well. Sure, all her dreams hadn't come true, but dreams change. People change. She wasn't a kid anymore.

Exhausted, she climbed out of the cab then up the front steps to her brownstone. She could hear Sinatra playing over the intercom sound system the second she opened the door. That could only mean one thing: Logan was entertaining clients that night. She prayed she wouldn't have to come along.

"Logan," she called out, heading toward the kitchen.

She stopped in the doorway and watched as he leaned against the granite counter that ran the length of the room, talking on his cell phone.

He was handsome – tall, blonde, powerful, athletic. He looked the part of that which he was – the quintessential wealthy New England Ivy League boy from a good family. She imagined any number of grandmothers getting on their knees and thanking God should he come through their granddaughters' doors.

Quite simply, he was everything Jess wasn't.

"Hi," she said entering the room, just as he'd finished his call.

"Hey you," he said closing the distance between them, stopping in front of her and kissing her on the check. "How was your day?"

"Fine," she lied seeing no point in telling him about Jess.

"That's great. Look, I need you to do something for me," he said placing his hands on her forearms.

She tensed. She knew what was coming. She also knew she couldn't handle it, not tonight.

"No."

"Rory, these clients could put us over the top. I just need you to put a little something together."

"Logan, I just got home and besides there isn't enough time. Can't you just take them out somewhere?"

He sighed, giving her a look of dismay. "C'mon," he said enveloping her in his arms and leaning his head against hers. "I wouldn't ask if it wasn't important."

Rory sighed. Hosting parties and going to functions was part and parcel of being a corporate wife (though technically they weren't even married); still, it was taxing – the dressing up, the sucking up, the need to be "on."

Instantly Jess's words echoed in her head: "Are you happy?"

"Please," Logan said rubbing her back. "Pretty please," he said as he pulled back, giving her his most pitiful look.

"Logan," she began.

"Thanks babe, I appreciate it. We make an awesome team," he said then kissed her on the cheek.

"But …."

She never finished the sentence. He was halfway down the hall before she could get the words out.