Time After Time - A Gilmore Girls Fanfic #1

Chapter 20

You're definitely missing out.

xoxo Em

With trepidation, he clicked on the attachment, not at all surprised to find a picture of nearly-naked people in a hot tub with the snow-capped mountains in the background. And there, right in the center, was a beaming Emmeline, holding a glass of red wine in the air. Not for the first time, he wondered how a self-professed party girl could command a board room full of suits or hold court during press conferences, but somehow, Emmeline Waters had a handle on it. And, most impressive of all, she looked to be having fun every step of the way.

Jess shook his head as he closed her email and began to go through the rest. Not for nothing, he liked his reclusive tendencies. Still, the image of Emmeline and her friends remained with him, nagging him with the question: When was the last time you really let loose and had fun?

After Jess finished a conference call to Penguin, having assured them that the books would be delivered on time, he turned off his computer and turned off the lights.

"Headed out?" Mark asked as Jess passed by.

"Yep. Meeting up with a friend for an early dinner," he said. "You should knock off early too."

Twenty minutes later, Jess stood just inside the entrance of Melrose Diner, scanning the place for a familiar face. When he spotted his friend Chris, he nodded and walked over to the booth in the back. Chris stood up and greeted him with a quick hug.

"What's up?" Chris said with a wide smile as he sat back down. "Long time no see."

"How are you?"

"Good. And how is Truncheon?"

After Jess relayed the goings on at the press, Chris shook his head. "Man, I do not miss it at all. Printing was stressful business."

Jess grinned. "It was nice to get my hands dirty though. Reminded me of the old days when it was just the three of us with those antiquated printing machines Larry, Curly, and Moe."

"Yes, we were a real comedy act back then," Chris said just as the waitress came by and took their orders.

"So how are Sarah and the kids? I haven't seen them in a while," Jess asked.

"I know this is a classic married guy move, but, here..." Chris held out his phone and showed off pictures of his family. "These were taken on Thanksgiving. Keep in mind that the boys are not normally that well groomed."

As Jess looked over the photos of the seemingly happy family, he couldn't help but compare it to Emmeline's photo. In the same afternoon, Jess had been presented with two wildly different lifestyles: First of the young, carefree kind; the other steeped in responsibility and adulthood. Both lives guaranteed fun—as well as promised a lot of sleepless nights—but the only difference was that, with the latter, you had the privilege of waking up to the same person for the rest of your life.

Jess leaned back and studied his friend. Chris Robinson had definitely evolved over the years from the tall, skinny guy with dreadlocks to the tall, not-as-skinny guy with the short, sensible haircut. After leaving Truncheon, Chris had gone into accounting and, while Jess might never understand why anyone would choose to work with numbers day in and day out, Chris seemed as if he wanted for nothing.

"You happy?" Jess asked.

Chris looked up at him in surprise. "Yeah. Yeah, I am," he said with a half-smile. "Work is steady and comfortable. The kids are doing really well in school, but neither one is showing any signs of being into poetry. Yet. And Sarah is..." He stopped, a pensive quality glossing over his features. "Well, she's my Sarah."

"That's really good to hear. I'm happy for you," Jess said with a smile.

"What about you?" Chris asked. "Still with that girl with the purple hair?"

Jess frowned at the mention of his ex-girlfriend, Desirae. "We broke up a while ago."

"Good. Because that girl was reaching Britney-with-an-umbrella levels of crazy."

Jess looked away, unwilling to talk about Desirae, afraid that whatever he said would make her look mentally unstable. Truth was, it had been nothing but a classic case of a relationship that had run its course. Sure, Desirae had handled the breakup badly, but who was he to judge? He used to be the king of making terrible choices. "It just wasn't meant to be," he said with a shrug.

"If that's the case, Sarah has a friend that I'd like you to meet."

"I'm actually seeing someone," Jess said, the thought of Rory warming his chest. He wondered where she was at that moment, what she was thinking. Was she reading another one of his books, accidentally stumbling onto another iteration of herself?

"Who?" Chris asked.

"Rory."

Chris' eyes grew wide. "Yale Rory? Rory, the girl you credit for all your success? Rory of that tiny little town you escaped from? Rory, the girl who chose that trust-fund jackhole over you?" Chris leaned back, shaking his head. "Yeah. Never heard of her."

Jess snorted. "So I might have talked about her a little."

Chris raised an eyebrow.

"Okay, a lot." Jess' eyes flicked around the room but for all the thoughts running through his head, he couldn't give voice to a single one.

"So you managed to win back the heart of the legendary Rory Gilmore," Chris said with something like awe in his voice.

"Yeah." Jess played with a napkin on the table, twisting its corners into points. "But she's very different from the girl she used to be."

"Well, you're not the girl you used to be either," Chris quipped.

A smile touched Jess' lips. "That's true."

Chris looked at him for a long time before finally saying, "You know, it happens more often than you may think. High school sweethearts reunite after many years and find that the spark is gone, that the relationship doesn't hold up to what they remember."

Jess shook his head. "That's not it. I mean, yeah, it's different. The feelings are definitely still there, though, but even that's different. It's more..." He stopped, his chest tightening at the thought of having Rory in his arms, in his bed, in his life. "More..."

"Say more no more," he said with a grin. "So, then, what's wrong?"

Jess looked up as image after image flipped before his eyes, of nearly-naked hot tub parties and kids with cranberry sauce smeared on their faces. "You ever get that feeling, like you're standing on a precipice and you have to either turn back to your old life or leap into the unknown?"

"Yeah," Chris said without hesitation. "Right before Sarah and I got married. And again when my first was born."

"You ever regret it?"

Chris cocked his head, one eyebrow raised. "What do you think?"

Jess nodded, letting out a breath. "I think you got everything you ever wanted."