Author- Archangel

Date- May 5th, 2002

Rating- PG-13, at least for now

Summary- It's the future, and when Rory and Tristan are forced to go on a trip, their children stay together.

Distribution- If you ask, go ahead

Disclaimer- not mine. Amy Sherman-Palladino and the WB's. Joshua, Julie, Chris, Caleb, Jacob, Jessica, Lori, Andy and Andrew are mine, but the last names aren't, if that makes any sense.

This story will be really confusing so I'm uploading a family history since we've last seen Tristan and a family tree to help the readers. Anyways, it's future and unforeseen problems throw Rory and Tristan, as well as their children, together.

Background:


Towards the end of Rory Gilmore's junior year, her world changed. That April, Tristan DuGrey escaped from military school unbeknownst to his parents. Rory's mother, Lorelai, having had a rough childhood herself, took sympathy on Tristan and offered him a place to stay, knowing he couldn't go home. Tristan gladly accepted and he and Rory quickly became friends. However, by the beginning of May, their relationship had changed. Tristan and Rory slept together.

At the beginning of July, Rory found out she was pregnant with twins. They were due at the end of February in her senior year. Tristan promised to help her out however he could, and when the twins, Andrew Robert and Amanda Lee Gilmore-DuGrey, were born March 3rd, 2003.

During Rory's freshman year of college (at Harvard, of course), she and Jess Mariano began a serious relationship. By the beginning of sophomore year, she and Jess were married. On June 16, 2005, their first daughter, Lorelai Marie Gilmore-Mariano, was born, carrying on the first name legacy.

Rory hadn't spoken to her best friend, Lane Kim, in over six years, so, when Lane called out of the blue in the summer of 2008, reminding Jess of a high school reunion, Rory couldn't resist going. The reunion turned out to be the worst night of her life. Her ex-boyfriend, Dean Hart, was there. Always the possessive type, he was jealous the second Rory walked in with Jess. Although he himself was married to Alyssa St. James, Sookie's niece, who was expecting their second child, his feelings for Rory had never diminished. That night, he raped her. Their son, Caleb Peter Gilmore, was born on June 15, 2009. Dean Hart is currently serving time in the state penitentiary.

Jess was perfectly understanding, acting the part of the perfect husband. However, it wasn't until May 7, 2015 when their next child, Jacob Gregory Gilmore-Mariano, was born.

A year later, Tristan reentered Rory's life. He had just been divorced, and he was having a hard time. The two got too close once again, and on September 6, 2017, their child, Katarina Julia Gilmore-DuGrey was born.

Rory and Jess had a lot of trouble with their marriage after that, but they never fell out of love. After less than a year of marriage counseling, Rory was pregnant again. On April 6, 2019, Adriana Callista Gilmore-Mariano was born.

Rory and Jess were more in love than ever and Rory was once again pregnant two years later. Tragically, Jess died on a photo shoot in Israel on September 24, 2020. When she was eight months pregnant, on February 10, 2021, Rory's friend, Brittany, took Adriana to a doctor's appointment. On the ride home, a drunk driver in the next lane hit the passenger side of the car, and Adriana died instantly. Rory never talked to Brittany again. One March 21, 2020, Rory and Jess's last child, Jessica Lynn Gilmore-Mariano, was born.


During this time, Tristan had also "moved on," in some strange sense of the words. He had gotten married at the end of his freshman year of college. However, his father called it a "necessary merger." He had married Skye Winthrop, heir to Winthrop, Inc. By marrying her, he had linked two of the most powerful families in Hartford.

By the middle of their sophomore year, Skye had produced an heir, Joshua Michael DuGrey, born on December 25, 2004, Christmas Day. Their second child, a girl, was born on April 19, 2006. Her name was Julie Melissa DuGrey. Two years later, on November 11, 2008, they had a son, Christopher Nicholas DuGrey.

Tristan and Skye were divorced less than eight years later, on March 28, 2016.