Prologue

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1984-2001

September of 1984

Jess Gilmore is born in a small hospital in New York City to 16-year-old Liz Gilmore. She had left home 6 months prior when she was 12 weeks along. Now she had a baby boy in her arms and wondering how she got her life so far off track.

October of 1984

Jane Mariano gave birth to Rory Danes. She gave Luke complete custody of their daughter and left as soon as possible. That was the last time she was seen in the state of Connecticut. Luke wasn't with Jane when she signed the papers. He was in another room of the hospital with his very sick father telling him about Rory's birth. When a nurse walked in with the papers he was confused. They hadn't talked about this. This wasn't their plan. But that's what happened.

December of 1986

Luke's father was dead. Luke was 18. Rory was 2. Luke was just out of high school and had decided against college because he wanted to be close to his dad. Plus, he had Rory. She was smart for a kid her age. But as smart as she was, death wasn't an easy thing to explain to a two-year-old.

This was the year Lorelai moved to Stars Hollow. She got a job at the local inn and started going to business classes. She chose this over being a legacy student at Yale. Her parents disapproved but they saw this as a good choice in comparison to her sister Liz's life. Liz was off in New York with a two-year-old. They saw her twice a year, Christmas and Easter.

January of 1987

This was the first time Liz saw Chris since she left Hartford. This was the first time Jess met his father. It was messy at first. Liz and Chris yelled. Jess watched. Then the yelling stopped and they gave each other sympathetic looks. Apologizes were exchanged. Later that night Chris came to the apartment Liz and Jess lived it. It was late, Jess was asleep. Liz and Chris slept together. He left in the morning and she cried. This was not the last time.

March of 1987

Luke opened the diner. He had turned his father's hardware store into a diner and moved himself and Rory into the apartment upstairs. A week after opening Lorelai entered the diner. She sat down with the little girl at a table and struck up a conversation with the toddler. The two became fast friends and Lorelai came to the diner almost every day.

June of 1989

Lorelai graduated college and had been promoted to manager of the Independence Inn. After having a fancy dinner with her parents and giving Liz a call she celebrates with Sookie, Luke, and Rory. They simply just ate in Lukes. It was simple it was nice and it was recognization for the fact she did something good and didn't waste her life partying like she did her teenage years.

November of 1990

Liz starts drinking. Jess is five and doesn't get it. He simply notices his mom having more mood swings. Some days she's happy, other days she crying for Chris, and sometimes she's mad. Occasionally she'd even bring a guy home. Jess never asked questions. He was in kindergarten now and was making friends and beginning to read a lot. One of the day's Liz was sober she got him a library card.

Meanwhile, Rory was in kindergarten and begun her love of learning that she would continue to have the rest of her life. It was around this time she met her life long best friend, Lane. Lane, Lorelai, school, and most importantly, Luke, was what Rory had. And it was all she needed. Well, that and her books. Rory had started a collection of children's books. The books she had were one's most kids in second or third-grade read. However, she learned to read them and memorize hard words. She was a smart kid.

April of 1996

10-year-old Jess understood his mom was drunk all the time. He didn't like it when she was drunk so he started going out by himself. He started reading constantly. Jess learned to be street and book smart. He navigated his way around the city. But he also became more anti-social. Turns out fewer parents are inclined to let their kid hang out with someone who roams the city with no adult supervision constantly. One day Jess found his way to Washington Square Park. He saw it as an upgrade from Central Park. So he began reading there.

May of 1997

Liz went sober for a month. She held her job down, spent time with Jess, and stopped bringing guys around. Then Chris showed up. He didn't sleep with Liz. They talked and he hung out with Jess. It was refreshing for Jess. Until it was time for him to leave. For the first time in a month, Liz came back drunk. She started to yell at Chris, told him to stay or stop coming back. He didn't come back for a while and Liz was back to being Liz.

On the other hand, Rory was doing great. She studied, did all her homework, got good grades. She even offered to help Luke around the diner constantly. Luke couldn't be luckier. His daughter was the spitting image of perfection, the most put together eleven-year-old there was. She excelled at everything she did, well except physical activity. But she made up for that in research. Luke tried to get her to play sports and when she discovered she wasn't very good at it she looked up everything she needed to know in order to watch sports with Luke instead.

February of 1999

Jess skipped a full day of school for the first time. At this point, he had almost no friends and started smoking. He knew he shouldn't but in a way, it was his escape from his terrible home life. The days he went to school people stayed away from him. Then one day his name was on the news. Well, not his name, his last name. His grandfather apparently made a fancy business deal. It made kids wonder. Gilmore wasn't exactly a common name.

August of 2000

Dean arrived in Star's Hollow. Rory liked Dean. Dean liked Rory. Luke didn't like Dean. But Luke excepted Dean. Rory and Dean dated and as long as Rory was home by curfew there were no issues. Lorelai told Luke, Dean was a good first boyfriend. Then she told a horifying story about her first boyfriend that scared Luke half to death.

November of 2000

Dean said the three words. Rory wasn't ready. Then he dumped her. Luke was angry. Rory convinced him to do nothing. He refused to serve Dean, but that was better then him almost fighting Dean. Rory ignored Dean at school. She didn't go into the market he worked in. Lorelai was there when Rory needed her.

In New York, Jess was staying out all night. Getting into fights the few days he went to school. He took care of Liz though. No matter what he took care of Liz.

January of 2001

Liz called Lorelai after Jess hit her boyfriend. She called Jess out of control. Told Lorelai about him skipping school, staying out all night, and smoking. This wasn't the Jess Lorelai saw twice a year. When Liz asked Lorelai to take him she said yes. Jess came home and found his things packed in boxes. He was informed he was being kicked out and sent to the hick town his aunt lives in.

The man he hit had hit Liz. So Jess hit him back. Now he was being sent away. Jess was almost certain this was his idea. Not Liz. This guy was going to be gone by the end of the week while Jess had to live in the middle of nowhere.

Lorelai made some calls and decided to get Jess enrolled at Chilton. She went furniture shopping and cleaned out her crafts room. She called the Gilmore's and arranged for Friday night dinners. She thought it might help, he acted put together around them and from what Liz told her she thought that is what he would need.

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⏰ Last updated: Sep 08, 2021 ⏰

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