If you have stalked my profile, or know me, you know that my uncle died suddenly of a heart attack last week. I've just been on a short hiatus being with my family and grieving. I'm sure everyone understands. I didn't want to post just an author's note because I had big plans for this chapter and I wasn't going to tease. Two of my favorite parts to write so far are in this chapter, so I hope you enjoy them and kudos to anyone who can figure out which ones.

I edited out a huge chuck of Rory from this chapter because it was getting uncharacteristically long and I felt that it would fit better in the next chapter, as there is plenty of description here without it. I'm pacing the story along slower that I would usually because Rory only has a week with Jess, so I really want to focus on that. Also note that Rory is leaning on marriage and she and Jess do have some morals, never mind the fact that Jess is still a bit bruised from her last departure, so I can't promise anything physical as of yet.

Phew. Sorry about the super long note. Thanks for reading and don't forget to review, as they keep me motivated! I will try to respond if I have time!

Disclaimer: I still don't own anything.

Maybe I am different, maybe I'm a fool
I wonder if it's worth it, trying to find another you

What are we heading for?
What do I dare again?
Once beaten, twice shy
And still we haven't learned

Jess wrapped his lo mein around his chopsticks as he and Rory sat on the sofa. He had changed out of his work clothes and was wearing a dark shirt and a pair of jeans. It had been too long since he had eaten out of a cardboard box while sitting in the living room. Life had just gotten away from him, he guessed. It was disheartening, but that was just the way things had to be.

"So you're getting married."

Rory almost choked on her beef teriyaki. "Ease into dinner conversation, why don't you?" she asked, dropping the rest of her teriyaki into the box.

"Sorry," he said.

"It was just blunt," she said, wiping the sauce from the corners of her mouth. "And I don't know if I'm getting married yet."

"You're wearing the ring."

"It feels weird not wearing the ring," she admitted, turning it on her finger. There was no way she was going to be able to keep eating through this chat.

Jess had sensed that she was nervous, but at least she was talking. It was really all he wanted, that and an explanation. He dipped back into the box for more lo mein before he continued. "But you love him, don't you?"

Rory pursed her lips, trying to decide what to say. This was something she would discuss with her best friend, but not her ex-boyfriend. "Yeah," she squeaked, as if it were obvious. "Of course I love him."

"Of course."

"He's great."

"I bet he is."

Rory nodded. "He is," she repeated.

"I wonder if he has a name, though." Jess stuck his chopsticks in the lo mein and swirled until the noodles tangled around the wood.

"Matthew. Matt," Rory said.

He nodded, wondering if he even wanted to know more. "How long have you and Matt been together?" he asked. He put down the carton to stop fidgeting.

"A little over three years."

A little over three years. Much longer than they had been together. He grabbed for the carton of lo mein to busy his hands again. Asking questions might have been a mistake. "That's…good," he said weakly, after realizing that she was looking at him rather expectantly.

"Yeah." She stared down at her beef teriyaki, hoping for the right answers. "Maybe we shouldn't talk about him."

"I thought that was the reason you were here," Jess said, pressing on. All or nothing. Might as well.

She paused. "Well, yeah. I guess. But…" Rory trailed off, her eyes darting from the teriyaki to Jess.

"So why shouldn't we talk then?"

"I don't know," Rory said. "This just feels awkward right now. I came here because I needed a friend that wouldn't judge me. I feel like you're judging me."

"I'm not judging you. And why couldn't you have gone to a friend that actually lived near you?" he asked suddenly.

"Because you know me!" she said. "You know me better than anyone."

Jess scoffed and tossed his lo mein on the coffee table. "You're kidding me, right? I know jack shit about you, Gilmore."

"You'd be able to tell if I was making a mistake."

"How? How would I know if you were making a mistake? I don't know you and I don't know him."

"You do too. You do too…know me." She trailed off.

Jess shook his head. "This conversation was a bad idea."

"I know it was."

Jess went back to his Chinese food and tried not to point out the awkward silence. There had been a time when there was no such thing as an awkward silence between them.

"So how's grad school?" Rory asked, hoping to start another conversation that didn't involve her potential marriage.

"It's okay," Jess said. "It's…educational."

Unable to hide it, Rory cracked a smile. She loved Jess and his vague answers. It was one of the many reasons she gravitated towards him. "Sounds great," she said.

"Yeah. It'll be nice to finally get the degree and move on. Maybe then I can have a social life. If I'm not too old by the time I finally finish with school." He smiled out of the corner of his mouth. "What about you?"

"What about me?" Rory asked, wondering why he could only talk about himself for so long before shifting the subject to her life.

"Yeah. I know you have a job and all, but have you considered going back to school?"

Had she? Yes. Rory didn't know if the money allowed, as she was still paying off her share of the Harvard loans. Financially, she wasn't even sure how Jess had jumped from Stanford to Columbia. Luke had put aside plenty of money, but it wouldn't have covered Stanford, let alone Columbia, if he were even still paying. Plus now that she was settling down, how would she be able to move to grad school as a wife and eventually a mother? Could she tell Jess that, though? "Not really." Nope.

"Just figured you would," Jess said, shrugging.

Their conversation tapered off as they finished eating dinner. It had been somewhat successful, to say the least. Rory was glad they had gotten the painful chat about Matthew out of the way while they still had the chance to further bond.

"I have to grade stuff and go to bed," Jess said, starting to pick up the trash and clear food from his coffee table.

Rory nodded and started to help him toss the empty containers. "Early morning tomorrow?" she asked.

He nodded. "Really early."

"I guess I'll probably see you in the morning then?" she asked.

"Yeah," he said. "I'll make the coffee."

She nodded her thanks. "Good night, Jess."

"Night, Rory."

"I don't understand why you can't just go on a date," Luke said.

"I have been on plenty of dates," Jess reasoned, sipping his coffee.

They were sitting in a small café near his apartment. What had started out as innocent small talk had turned into Luke jumping down his throat about the pining he wasn't doing.

"And?" Luke pressed.

"And it didn't work out," Jess said with a shrug. "I've gotten laid plenty of times, in case you were about to ask if I was getting a cat." Jess smirked, knowing the statement would either irritate or horrify Luke.

Luke did cringe, but he realized Jess had told him that mainly for the reaction. It was just fun for Jess to see him squirm. "Well, that's great," Luke said.

"Yup."

"You're twenty-two."

"Really? I didn't get that memo."

"I just mean that you should get out more," Luke said.

"No offense, but are you really the guy to give me dating advice?" Jess asked. "You never even leave the diner."

"I'm not really giving you any advice," Luke said.

"Okay, so what are you doing then? Jess asked.

"Making a point."

"So make it."

"You have spent over two years trying to get over Rory. That's longer than you were even together. If you went out and dated, maybe you would find someone else."

Jess rolled his eyes. "There's plenty of fish in the sea. Blah, blah, blah. I know the whole speech. I've gotten it before. I just don't want to date, okay? I didn't see the point before I with Rory and I don't suddenly see the point now."

"Okay. Just know that you could be passing up something by being hung up on the same person for so long," Luke warned. "It might even make you happy."

"Sure, whatever," Jess said, brushing him off again.

"Why don't you have real milk?" Rory asked, closing the refrigerator door. She had yet to ask him and was sick of eating her cereal dry in the morning.

"I'm lactose intolerant," Jess answered, briefly looking up from pouring soy milk on his cornflakes.

"Lactose intolerant?" Rory scoffed. "You are not."

Jess nodded and sloshed his corn flakes around in the bowl. "Yeah, I am."

"No. Since when?"

"I guess about six years," Jess said. "I just started having trouble digesting dairy, so my doctor harassed me about tests and here we are." He shrugged. "No big deal. I just drink soy milk and eat lactose free everything."

"What about ice cream?" Rory asked.

"Lactaid pills. It's not a permanent solution, but then I can eat some dairy products after I take them."

"Oh." Rory drank some of her coffee. It was weird, some of the things she didn't know about Jess.

"I've got to get going soon," Jess said, getting up to put his bowl in the sink. He grabbed a travel mug to pour some coffee in and did a once over of his clothes. He paused to straighten his tie and make sure his pants covered the Vans logo on the side of his sneakers. "Feel free to go in my bedroom," he said. "That's where all the good books you've been looking for are hiding."

Rory grinned. "Are you sure it isn't going to be an invasion of privacy?" she asked.

"I'm inviting you in," Jess pointed out.

"Yeah," Rory said. "I just didn't want to be where I shouldn't." She paused. "Thank you."

Ignoring her babbling, Jess breezed out of the kitchen to brush his teeth.

Rory nursed her coffee and tried to think of something else to say.

"I'll be back by five, hopefully," Jess said, emerging with his jacket already on and his messenger bag slung over his shoulder.

"Okay." She nodded mechanically and watched him shut the door as he left.

Jess Mariano had been on his fair share of dates. It had taken a year for him to fully kick dirt over his wounds, but he had buried any thoughts that led back to her. Or so he let people believe. Patrick had set him up with a girl once, but he never called her back because she was a double major in communications and international relations. When Patrick asked why, Jess shrugged and claimed she just wasn't his type.

There was one girl from his European literature class that Jess asked out for coffee. Coffee became dinner and dinner became sex. But all bets were off as soon as Jess discovered that she hated Hemingway and loved Ayn Rand.

He knew small similarities were unavoidable and not something to base a relationship on, but he still strived to find someone who was completely different.

Jess met Liza in the beginning of his senior year at Stanford. She was strong and independent, well read and well versed – a psychology major to boot. He didn't like her instantly, but she did grow on him.

They sat in class and engaged in small talk before they started dating. As it was becoming his first serious relationship since dating again, Jess tried to learn from his mistakes. He became the ideal boyfriend and felt that he was getting the same attention back. Jess even stepped up and left his toothbrush and a change of clothes at Liza's apartment.

Three months with Liza was all it took for Jess to blow the dirt off his scars. Every little thing Liza did was compared to Rory. His heart ached to even think about her. And then Liza found on Jess planned to move back east for grad school.

Oddly enough, Jess and Liza broke up merely because of her reaction to his decision of moving east and not the fact that they would be holding onto a long distance relationship. Jess wasn't even sure he could stomach another long distance relationship and the turmoil it brought ever again, but the potential move was enough for him to cut ties early.

After Jess moved east, he started dating women left and right. Part of that was just to cover up the daily pain he felt and the need to move on. No one suited him. No one complemented him. And so, he send card after card in the hopes that Rory would at least pick up the phone to say hello.

His hopes waned as he grew older. He slept with women more than he dated them and received flak from Luke because he was passing up the same opportunities he did in life. With grad school and teaching, Jess buried himself in work and barely left his apartment for anything that didn't involve education. School had become his life and he was becoming the kind of teacher he would have laughed at years ago.

Everyone always asked how he was single, being the "catch" that he was, and he always offered up a smirk or a shy smile and the explanation of being busy or that the right person hadn't come along yet.

Well, at least part of that was on base.

The right person had come along, but she had swiftly left.

Left him in the dust.

And Jess could not help but incessantly pine, the one thing he promised himself that he would never do.

At the end of the day, Jess packed up his things and headed over to the main office to pick up his mail and wait for the staff meeting to begin. It had been a long day, but his spirits were still pretty high. The day wasn't draining him at all. There had been an inquiry on when the projects would be graded, the assignment Jess had simply pushed aside due to Rory return, but that was the only thing that was weighing down on his mind.

There were still students rummaging through lockers, changing from dress shoes to sneakers, and slipping pants on under their pleated skirts, as Jess navigated through the hallway to Cindy in the main office.

He leaned casually against her desk. "So if I were to hypothetically sign up for the teacher student softball game," Jess said, "how would I go about doing that?"

Cindy grinned and pulled out one of the pens that secured her hair in the tight bun. "Well, hypothetically, you would tell me you wanted to sign up and I'd give you the list." She handed him a clipboard with the sign up sheet clasped shut against the wood. "And you'd sign your name." She winked at him. "Hypothetically, of course." She retracted the clipboard, tucked the pen back into her hair-do, and pushed her glasses back up the bridge of her nose.

Jess rolled his eyes and leaned against Cindy's desk. "You're not going to make this easy for me, are you?"

"Make what easy?" she asked in a syrupy sweet voice.

Jess rolled his eyes again. "Okay. I want to sign up for the teacher student softball game."

Grinning, Cindy grabbed the clipboard and took the pen out of her hair again. "Sign your name. I wish I could get this blood."

Jess raised an eyebrow and smirked as he accepted the pen and clipboard before adding his name to the bottom of the list and signing with a flourish. Jess was actually in the mood for small talk with Cindy, and he glanced at her expectantly as he let the clipboard hover over her desk.

"You seem like you're in a good mood today," she noted, accepting the clipboard and the smile.

"I'm okay," he said.

"Knock me dead with a feather, Mariano. I can see right through that smirk of yours." She rolled her eyes and pushed her desk chair away from the desk to tuck away the clipboard.

"Please. I'm not that transparent," he argued, dropping his bag on the floor. It was obvious he was going to be standing by Cindy's desk a bit longer before the staff meeting.

"You are. I've known you for years." She pointed a finger at him. "You got laid last night."

Jess cringed and peaked into the hallway. "Jesus. Say it louder. It's not like we're in a Catholic school or anything. I don't want my students to think I'm easy."

She laughed heartily. "Because Jess Mariano is man of virtues and morals." He smirked again. "Yeah, I didn't think so."

A thin flush spread across his cheeks. "I did not "get laid" last night," he said, using his fingers for air quotes. "I just had a conversation with an old friend. It was nice."

"Sure," Cindy said. "And the sky's blue."

"Actually, it is. Last I checked, anyway."

"Whatever," Cindy said, brushing off his statement. She looked at the clock on the opposite wall. "You're trying to hold me up, aren't you?" she asked.

"For what? The meeting?" he asked, tilting his head to view the time.

"No, lunch," she scoffed. "Of course, the meeting. Come on." She smoothed the wrinkles from her skirt and hustled Jess along, who grabbed his mail from his box as she shoved him into the conference room.

Rory was getting bored just sitting around the empty apartment. At first, she was leery about poking into Jess's private things, but she eventually creaked open his door. She was shocked at the sheer amount of books that lined his walls. Except for the space his bed, desk, and closet occupied, the entire room was full of books.

The corners of his sheets were folded over and a pair of wire-rimmed glasses lay against the top of a book on his nightstand. Jess made his bed? Jess wore glasses? Since when? Jess was right; she really didn't know anything about him.

Rory dropped into the desk chair and studied the surface. His textbook was sitting on his desk next to a binder. Carefully, Rory flipped up the lid of the book and scanned the pages. She may have been the valedictorian in high school, but Jess was definitely pulling ahead of her. Sighing, Rory shut the book and allowed her eyes to wander around the room.

It was a comfortable set up, but it was obvious that Jess didn't spend as much time in his room as he did the rest of the apartment. Rory wondered what women thought when he brought them home. Did he bring women home? He had to – this was Jess after all. The same Jess that wouldn't settle on a long-term relationship until they dated. How much had changed in his dating life compared with his every day life? Who was she to say that he wasn't in a relationship now? At this point, Jess could be sharing an underwear drawer or closet space and she wouldn't know because it wasn't something he would tell her.

It felt intrusive, and wasn't her at all, but Rory jumped out her seat and opened the dresser drawers. All of his weekend and after school clothing, save for the undershirts and boxers, were folded neatly and tucked in the drawer. Not one scrap of pink or lace. The closet was the same, but all of his button down shirts, ties, and black and khaki pants lived in there. A row of shoes ran across the lower part of the closet. There were two colors of Converse Chuck Taylors, a space where his Vans usually rested, and two pairs of dress shoes. In the back of the closet rested a black guitar case.

Rory never knew Jess to be so organized. When they were together and Jess lived at Luke's, all his clothes were just shoved in the drawers and his shoes disappeared into the abyss under his bed. Sighing, Rory shut the closet door. Snooping was not her first intention when she entered the room. She felt like such a…snoop! Trying to focus on what Jess really had in mind when letting her in his room, she neared the bookcases.

At first look, Rory couldn't figure out the organization. She was sure Jess had some system worked out, but it was something she could ignore at the moment. His vast collection of Hemingway novels sat on one shelf. All his favorites were in one place, separated from the rest of his books in the other room. Mentally marking where the books she wanted to read were located, Rory scanned the second bookcase before her eyes fell on a particular name.

Jess Mariano.

Her fingers grabbed for the book and she sat on the floor, hands shaking. It was a thin paperback volume that was covered in a layer of dust and was so pristine that she bet it had never been opened. The cover of the book stared back at her as the minutes ticked by. She couldn't bring herself to open the book, never mind start reading it.

Sticking to what was easy, Rory carefully spread open the cover and turned the first page. Her eyes caught the dedication and her breath caught in her throat.

To Rory - My inspiration for everything. Sometimes the words unsaid always make the most impact.

She read the dedication over and over again, but she still couldn't process it in her mind. A tingle ran down her spine and she shoved the little paperback into the gap in the shelf where she had taken it. Her stomach clenched as she got up and ran into his bathroom to throw up in the sink.