So this is an MP3 shuffle for Rory and Jess, my favorite Gilmore Girl couple! I had the hardest time writing this because my new computer had Word Starter 2010 and I originally started this in Word 2003 and 2010 won't even acknowledge my documents, let alone let me edit them, so luckily I was able to upload and finish the story here! Yay! But I still have to figure that Word thing out :( I'll figure it out eventually, but in the mean time, Happy Holidays!

I Wish- Omarion

Jess had been in love with Rory Gilmore since they were in high school. He immediately found himself charmed by her quirks and thirst for knowledge, and love of literature. He should've known he had fallen for her the second he laid eyes on her from the way his heart took off. And he wished he hadn't fallen.

Rory was with Dean. He was the town's wholesome boy, the best on the hockey team and a grocery bagger at the local market. Jess was the town's black sheep, the juvenile. No one knew what Rory saw in Jess; hell, neither did Jess. But she wanted him as a friend. She worked to make him feel included and made a permanent place for him in her heart. As a friend. He wasn't mad. How could he be? At least he had Rory Gilmore in his life.

This Time- Jonathan Rhys Meyers (from the August Rush Soundtrack)

Rory walked along the streets, debating whether to go to the place she'd came to Philly to go in the first place. To see him. She breathed in the cold air, and exhaled, ignoring her breath's visibility. She'd walked up to that door many times since she'd gotten there a few hours ago, but could never gather the courage to knock on his door. She rounded the corner again and looked up at his building across the street, the streetlights creating a glare on all the windows.

Rory looked at the entrance, wandering off in her thoughts. What if she didn't go to him? What if she left and never came back? Would she be happier without Jess or would she regret it? Rory turned, about to walk away but then turned back and headed across the street.

Colorful- Rocco Deluca & The Burden

"This is the best thing I've ever tasted," Rory said with a heavenly roll of her eyes, "I don't know why I didn't think of this before. Pickles! Dipped in chocolate!"

Jess frowned at the mere thought, never mind the fact he was watching his pregnant wife eat it. Lorelai even looked disgusted.

"Oh, babe. You really are pregnant."

"As if the baby bump wasn't obvious enough," Jess chuckled.

"It could just be a food baby," Rory pointed out.

"Or our baby overweight because she's filled with food."

"I have to eat for five Jess," Rory pointed out and Jess' head shot up from his book.

"Two portions for me, two for our baby, and then leftovers in case we want more. We have big appetites."

Every Time We Say Goodbye- Ray Charles and Betty Carter

Rory laid her head on Jess' chest and closed her eyes, inhaling his scent. She was surprised her mother actually allowed him to stay over, bedroom door open of course. Tomorrow morning she'd be off to Yale, and Jess would still be here. It wasn't that far away, but still, she was going to miss Jess. She'd already been away from him the entire summer, and though she had fun traveling through Europe with her mom, she really missed Jess.

She was content lying in his arms, him pressing soft kisses to her forehead and her hair. He never once asked her to stay, and she secretly kind of wanted him to. Instead, Jess pushed her to go. He told her she was destined for something big, and he wasn't going to hold her back.

She closed her eyes and breathed him in again, smiling to herself. She'd have to steal one of his shirts or something, because she was going to miss the smell of burgers, books, and something that was just uniquely Jess.

The Best of Me- Mya feat. Jadakiss

Rory blushed at the way she was being looked at. 'This has to stop. I have a boyfriend! Dean! Cute, tall, handsome, Dean'

And she'd told Jess this countless times, yet he still shamelessly flirted with her, even doing so in front of her boyfriend who did not take kindly to it.

She knew it was wrong and she felt guilty for even considering it, but she wondered what it would be like to be with Jess. She and Jess both liked books and music. They kind of had same sense of humor too. Jess was smart, witty, mysterious and intriguing, having a bad boy finesse about him. She was kind of drawn to it… and him.

'No! I can't let him mess with my head…'

"More coffee, Rory Gilmore?"

Rory smiled shyly, blushing and nodding.

What Took You So Long- Emma Bunton

"You should've just told me."

Jess turned around to find his ex-girlfriend. Bright blue eyes, the brightest blue he'd ever seen, staring back into his brown ones. He turned back to the lake.

"How did you know I was here?" he asked.

Rory scoffed, "People in this town talk. That's should be one of the main things you remember about this town"

Jess smirked and nodded, not bothering to look over to her when she took a seat on the dock beside him.

"I would've understood had you told me, Jess. We could've worked it out or something."

"I wasn't sure what I wanted back then," he admitted, "I was confused and hurt and-"

"I would've been there for you, Jess. I would've helped."

"I know you would've," he said, finally looking at her, "but… I thought you deserved someone who wasn't as screwed up as me. You deserve so much better."

Put That Woman First- Jaheim

Jess hated watching Rory go through what she was with his so called best friend. He remembered when he'd first introduced them. It was a mistake to do so, probably the second biggest one he'd ever made. The first being he never admitted how he felt. And Logan seized the opportunity. Jess couldn't really complain. He told Logan straight out that he didn't like Rory that way, which was a lie.

Rory was currently sitting on his and Logan's living room couch, crying her eyes out. Logan, had cheated on her with an entire wedding party of bridesmaids when they had taken a "break". Jess walked over and sat beside her.

"This is my fault," he mumbled.

Rory's with dark greyish blue eyes looked to him.

"Had I-" he looked off and shook his head.

"Had you what?" Rory asked.

Jess looked at her, "This is," he chuckled, "horrible timing. But had I told you how I felt to begin with… maybe you would've been with me instead."

Bach/Break- Jonathan Rhys Meyers (from the August Rush Soundtrack)

When Jess came back to Stars Hollow, he'd shocked everyone. He was successful; an author/publisher who co-owned a book store that had gotten a lot of attention as of late. Everything seemed to be coming back together for him, pieces all falling into place, but he knew there was one piece he'd have to place himself. He just had to find her, hence his reason for being back in Stars Hollow. Rory Gilmore.

He knew Stars Hollow. People talked, and word spread quicker than wildfire. All he had to do was listen and he'd find her. And she'd find him.

He walked through the streets of Stars Hollow on his first night back and smiled when he found her, sitting on a bench looking back at him.

Gotta Make It- Trey Songz feat. Twista

"This isn't a break up, Rory. This is me saying that we're going to be together. I just want to be worthy of you first. I'm going to be successful, and I'm going to come back to you, and we're going to be together. I'm going to be something for you, Lorelai Gilmore."

He looked at her picture every day. Knowing she was the reward of all his hard work made him work even harder. It pained him having to let go of Rory, but it was the push he needed. He was going to be somebody for her. That's why he worked his way up in that newspaper, eventually writing articles by day and his book by night. She was why he made sure every part of his book was perfect. Rory was why he made it to number one on the bestseller lists. Had Rory not been the goal, he'd probably have never gone to school and did the things he did. But he knew he had to make it, for Rory.

And to see her smiling back at him, her hand in his as they walked down the aisle, he knew it was all worth it.

We'll Be A Dream- We the Kings feat. Demi Lovato

Jess had waited years for this moment; to find his childhood friend again. He remembered everything about her as if she was standing in front of him. He could see those blue eyes clearly, that sweet smile, and her familiar scent of the various candies and coffee. He grinned when he noticed her grinning back at him.

Rory couldn't fight the grin on her face from seeing Jess again. She had missed him. She missed hearing his voice, seeing his brown eyes glow with mischief or intrigue as they scanned over the words of one of the many books they read together. She missed the grin too, and every other facial expression. She was happy to see him back in Stars Hollow.