Ten Years Later
Jess looked up when he heard the chime in the diner door ring. Lindsay Forester had walked in. That meant the idiot Dean was in town. His eyes followed her till she sat at a table. Dean's wife was tall blonde and elegant. Every hair in place every piece of clothing beautifully tailored. She was totally devoid of jewelry except for a gold cross that adorned her neck and a simple gold wedding band.
Jess looked around. His uncle was nowhere to be seen, so it was up to him to wait on her. Jess walked over and stood wordlessly by her table. Lindsay sensing his presence looked up. After a moment's hesitation she spoke. "Coffee, black with an apple fritter." As soon as Lindsay spoke she dismissed him with her eyes.
Jess walked away fuming; she dismissed him like he was an errant roach. Life wasn't fair. It was him who should be sitting at the table and Lindsay should be waiting on him. When Jess returned with her order she was reading a legal paper of some sort. He set the coffee and pastry to her left. Lindsay didn't even acknowledge him; she kept on reading.
When Jess arrived at the counter his uncle Luke had re-appeared. "Luke I'm taking a break, I'll be back in twenty. Without waiting for a reply he took off his apron and threw it on the counter and strode out of the diner. Jess walked across the street and lit a cigarette.
Jess took a deep pull on his cigarette and let the smoke slowly drift out of his nostrils. His life wasn't supposed to be like this. He was going to conquer the world. His thoughts wandered back to when his mother married TJ. He didn't want to attend the wedding, but Luke insisted and to his surprise he had a good time. After the wedding he was going to attend to the other reason he returned to Connecticut. It was time for him and Rory to be together and leave Stars Hollow. They were both smart. The world would be their oyster.
Through his conversations with Luke he found out that Rory was still at Yale. He left Stars Hollow in the early evening and drove to New Haven. Finding the college wasn't hard. Luke told him what dorm Rory resided in. When he arrived at Rory's dorm; to his mortification the idiot Dean was standing with Rory talking. Screw Dean he decided. He joined the duo and without even acknowledging Dean's presence he spoke "Rory I need to talk to you."
Rory turned to Dean and spoke. "You need to go Dean."
Dean shrugged his shoulders and walked away wordlessly.
Rory opened her dorm door and Jess followed her in. To his delight Rory was packed up. Jess would never forget the conversation they had. It was short and to the point. "Rory you and I belong together, we've known it since the first time we met. I want to be with you. Come to New York with me."
Rory hesitated and when she spoke he couldn't believe it. "Yes Jess I'll go with you." He was on top of the world.
Jess's own loud sardonic laugh startled him. He didn't mean to laugh aloud. Jess reached into his shirt pocket and took out his pack of Salems; he wanted another cigarette. Jess thought back to his life in New York. His feeling of euphoria lasted all of eight weeks.
Job hunting did not go as well as he thought it would. He told the prospective employers how smart he was and they should hire him. All he got was you don't have a high school diploma sorry. Finally he found a job waiting tables in a diner in Queens.
Rory fared a bit better. She landed a job with the New York Times; not as a reporter, they were very unimpressed with her resume, but offered her a job as a receptionist. This wasn't quite how He envisioned life in New York, but it was doable.
Two months later his New York dreams came to a crashing halt. Rory was pregnant. They had no health insurance, and eventually she would have to quit her job. There was no way he could support a wife and child on wages and tips he made in a greasy spoon.
Jess made a call to his uncle Luke. After Jess explained his situation there was silence on the line. Finally Luke spoke. "Jess why do you have the talent to make a terrible situation worse?" Marry her and come back to Stars Hollow. I'll pay for the child and you can work off your debt to me by working at the diner."
Jess returned to Stars Hollow with his new bride on a rainy Saturday afternoon. He thought that Lorelai did not like him before, now he knew she despised him. Rory eventually went to work for her mother at the Inn. He was not allowed to set foot in the Inn, nor was he allowed to set foot in Lorelai's home.
Jess stood up and walked back to the diner. He ran into Lindsay on her way out. His bitterness was overflowing. "Lindsay."
Lindsay turned, looked at him before she spoke. "Are you talking to me?"
"Yes." He said sneeringly. "Who else would I be talking to?"
Lindsay started to turn away and leave. "You know Lindsay, you were his second choice." He had to take her smug ass down a notch.
Lindsay smiled at him. "Maybe so Jess, but I am his final choice. Isn't your first choice married to someone else now?"
Jess saw red. "Screw you Lindsay." Instead of entering the diner Jess turned and walked to the local pub. He needed a drink to calm him down. Once seated at the dark bar he ordered a shot of Ten High and a Pabst draft beer. As soon as his drinks arrived he downed the shot and slid the glass across the bar and nodded for a refill. Lindsay had hit a nerve.
Their daughter was born six months after their arrival. They named her Lynn. No particular reason; it just sounded good. Lynn Mariano. Two years after that Rory left him. They had an argument. Rory told him that she was fed up with his arrogant condescending attitude and he told her that he was tired of her fairy princess outlook on life. That was the opportunity Lorelai and her mother were waiting for. Before he could say boo; Rory was living with grandparents in Hartford. Two months later she was re-enrolled in Yale. Jess knew Richard Gilmore pulled some strings. Shortly thereafter he was served with divorce papers. Rory wanted no alimony no child support and full custody of Lynn.
So he was back where he started waiting tables in his uncle's diner. Two years after graduating Yale Rory had run into a former classmate of hers from Chilton. Jess met him a couple of times when Rory brought Lynn for his visits. The fact that Rory married a guy her grandparents approved of pissed him off. Some rich blonde idiot named Tristan married her. He hated how Tristan looked down at him.
Jess ordered another shot. He knew Luke would be pissed off at him, but he was beyond caring. While he was floundering in Stars Hollow Dean and Lindsay put each other though collage. She became a corporate Lawyer. Dean received a degree in structural engineering and worked for the Quill group in Bridgeport. They had the life he and Rory should have had. His resentment was being fueled by the liquor. He realized the dress Lindsay was wearing probably cost more than he made in a week.
Stumbling out of the bar after his sixth shot of Ten High; Jess decided he wasn't going back to work. He needed to figure out his life. While walking he saw a Black GMC Yukon. He knew it was Dean's car. In his mind the car fitted Dean's personality perfectly; big stupid and useless. Jess took out his car keys and looked around. No one was paying any attention to him; he took his key and walked the length of the vehicle scrapping his key against the highly polished side. Jess looked back; the act of vandalism against Dean made him feel better.
To Be Continued…..