A/U: This story takes place almost 8 years after the last episode. Jess and Rory are about 32 years old throughout the story.
Jess Mariano looked out his car window as he drove. He had just passed the sign welcoming him to Stars Hollow and he felt as though he had just passed through an invisible force field as he felt a wave of memories wash over him. He hadn't really been around much. His mom, TJ, and Doula had often come to Philly to see him and he had even seen Luke a few times over the years. He really had no reason to return to Stars Hollow since that day at Truncheon when Rory had kissed him. That ultimately seemed like their ending or at least...it should have been.
About three months after her graduation at Yale, the entire family was dragged to Cape Cod for Luke and Lorelai's wedding. Jess had been given the privilege of being the best man and accepted his role with a smile. His wedding toast consisted of something like, "Finally!". Short, simple and to the point. Since he saw that kiss between himself and Rory as being their last, he wasn't as nervous to see the girl again. But when he arrived and saw her in that blue bridesmaid dress that matched her eyes, he melted and he realized that he still loved her even though he shouldn't.
At the reception they spent a lot of time talking about anything and everything. They had so much history that a book could be written. Maybe it was because they drank a little too much or laughed a little too often, but one thing led to another and the next morning they awoke in each other's arms without a care in the world. Both realized that this couldn't happen and that in mere hours the bliss of the night would fade away as reality took its place. Jess was still working on making it big with Truncheon and Rory had only started her journalistic dream three months prior. Neither had time to put the time and effort into the long overdue relationship so when Jess kissed her one last time before boarding the plane, tears fell but eventually things returned to normal.
Jess realized that though he loved her with all his heart, she deserved more than what he had to offer and that if he ever returned to Stars Hollow, he'd never be able to leave again. That was nearly 8 years ago...
Now, as Jess drove through the square, his blue VW Jetta filled with the necessities, he thought of how crazy he must be. By now she must be married with kids or something, right? She'd be crazy to want him back after all this time. But Jess Mariano hoped against hope as he parked in front of the Diner.
He looked the place over. It hadn't changed a bit. As he opened his car door, he was welcomed with a rush of cold winter air. He quickly stuffed his hands into his jacket pockets and ran inside. Once inside the diner, his eyes searched for Luke but he was nowhere to be found. He shed his jacket and scarf, hanging them on the back of his chair before sitting down. Before he could even take a second, nostalgic glance at the old place, a little boy wearing a visored beanie and a Luke-style blue flannel approached him with a pen and pad.
"What can I get ya sir?" The little boy asked hopeful, his blue-green eyes shining. Jess studied him for a moment. He was rather short and scrawny with dark shaggy brown hair peaking out beneath his beanie. He was a really good-looking kid and was definitely a Gilmore. He saw both Rory and Lorelai in this one and smiled. Jess knew that Lorelai and Luke had a son but hadn't seen any pictures since the kid was maybe a year old.
"Hey," Jess said nicely, "I think I'll have a doughnut." The little boy went to write it down before stopping abruptly.
"Are you sure? It's danish day you know. We have cherry and apple." The boy said with a Gilmore grin.
Jess chuckled. "Okay, I'll have one apple danish please." The boy looked pleased and scribbled something on his pad of paper before leaving. Jess watched as the boy climbed onto a stool and grabbed an apple danish, set it on a plate and brought it back to Jess, setting it in front of him.
Jess smiled. "Thanks. Do you know where Luke is?" The little boy smiled and nodded excitedly.
"You know Luke? You look familiar but I've never seen you around here...He's on his break, I think he might be at home. I'm here with Caesar doing my shift." He replied proudly. Jess grinned.
"Yeah, Luke is my uncle. Which would make me related to you in some way or another...I'm not sure but you can call me Uncle Jess if you'd like." Jess said kindly. He had never really gotten along with a kid this much and it almost surprised him.
"Hiya Uncle Jess. My name is Shane." The little boy smiled approvingly and tore off Jess's receipt, handing it to him. Jess took it but was surprised to see "Apple Danish, $1.25" written on the paper. Jess hadn't met very many five year olds that could write so well. Wait...was Luke's kid even five? No...seven maybe eight? Eh forget it.
"Wow, nice handwriting little man. You must take after Rory." Jess said, not really thinking much. This kid reminded him so much of his purpose here in town. He wanted to find Rory more than anything and see what her life was like now. "Do you know where she is? Does she still live in Stars Hollow?"
"Of course she lives here! She's at work right now though. Five days a week in New York City. It's really big there! She took me once and showed me her work and took me to really cool places like Washington Square Park!" Shane went on and on and just at the mention of his hometown, Jess felt as if Rory had gotten a job there because of him, maybe subconsciously.
"Hey Shane, can you do me a favor? Don't tell anyone that I'm here, okay? I really want to surprise Rory. She and I are old friends." Jess explained with a smile. Shane smiled and nodded as Jess got up and put his jacket and scarf back on.
"Bye Uncle Jess!" Shane said with a giant grin as Jess walked out. He loved meeting new people but now really wanted to tell his Mom about it. But Jess had said not to tell anyone. Maybe he would never know, Shane thought before spotting another customer. He shrugged it off with a smile before he continued helping the new customer.