Summary: futue fic- Rory became a journalist and married Jess who became an award-winning author. They livein Hartford near Emily, whohasmany health problems and is dying, though Richard died a few years before.Lorelai married Max, who still works at Chilton. They had a daughterwho they namedDiana Lorelai Medina. Diana grew up in Stars Hollow, and her boyfriend is Daniel Kim, Lane's adopted son. Now Diana is a freshman at Chilton and Tristan DuGrey is the headmaster!

Disclaimer: Everything you recognize from Gilmore Girls is Amy Sherman-Palladino's, not mine. I don't own anything else, except these ideas, of course, and Diana Lorelai Medina.

Lorelai sat at the kitchen table, eyes glued to her watch. Diana couldn't be late today. Lorelai didn't want running late on the first day of Chilton to be a family tradition.

Finally, Diana rushed downstairs wearing her Chilton uniform and matching Chilton backpack.

"Come on!" she shouted to Lorelai.

"Wait, wait. I'm not going, remember? Dad will take you. I have a meeting at the inn in…shoot! Twenty minutes!"

Lorelai ran upstairs as quickly as she could to make sure Max was ready to go. So when she opened her bedroom door to find him happily snoring, she panicked.

"Max! Max! Get up! Get up! GET UP!"

Max Medina slowly opened his eyes. He'd been having an incredibly weird dream about a talking firefly, so he was only half awake now.

"What happened? Is something wrong?"

"MAX!"

"What? What?"

"The summer's over, Honey. Welcome to reality, and right now reality is set on the first day back to school for both of you?"

"Both of us?"

"You and Diana!"

"Oh my God! I forgot!"

"No, no it's ok, she can take the bus, but you're going to be late for work!"

By this time Max had fallen back asleep.

"MAX!"

"Right, right. Okay, I'm here...what?"

Lorelai ran out of the room and down the stairs, which was particularly difficult on this so far coffee-less morning.

"Diana! Go, go. Get the bus."

"What? What bus?"

"The one to Hartford! GO! You're going to be late! Ah, and so am I!"

"What about Dad?"

"He'll catch up, just go!"

Diana ran to catch the bus. Luckily, it was just pulling up when she got to the stop. Any other day of school, she would've been late, but it was only the first day, and classes started two hours later. Unlike her sister, Rory, Diana was starting Chilton during Freshman year. After her mother's rant about how all other families have some kind of weird traditions, it was decided that the Gilmore-Medina tradition would be that everyone in the family goes to Chilton for high school. To add some dramatic effect, Lorelai made it that only girls would go to Chilton. It sounds more…well, traditional.

When Diana entered the building, she was shocked at the size of it. Only freshman roamed the halls looking for their orientation classrooms. Diana checked her schedule for the first week of school. 9:45: Freshman orientation in room 206. Much to her surprise, she found room 206 very easily. She walked into the large classroom with marble floors and beautifully carved wooden walls. Not knowing what else to do, Diana sat down to begin reading her brother-in-law's latest book: Tales of Minnesota's Underworld by Jess Mariano.

Only ten minutes later, a tall man who looked like he was in his mid-thirties, with blondish brown hair stepped into the room. Max, his tie loosened, and his hair a mess so that you could tell he rushed to get there, walked in after the other man, and stood behind the podium in the front of the room. He looked worried and sidetracked, but he smiled at Diana, cleared his throat, and sounding very professional, something completely new to Diana, addressed the Chilton freshmen.

"Good morning, students. My name is Mr. Medina. The majority of you will have me for English and Literature this coming school year. I'd like to introduce the person who will guide you through not only the rest of today's orientation, but will also guide you through all of your years here at Chilton: Headmaster DuGrey."

Max stepped back from the podium and the other man, who was apparently the Chilton headmaster, took his place. As Headmaster DuGrey began explaining the school rules, the freshman curriculum, and the importance of extracurricular activities, Diana pondered her dad's announcement.

"Headmaster DuGrey", he had said.

'DuGrey, DuGrey. I KNOW I've heard that somewhere. I KNOW it! And the headmaster, he looks…so familiar.'

"Well, yes, you can wear sneakers with your uniform. I'd recommend it in fact", said Headmaster DuGrey, answering someone's question.

Diana looked as her father, Mr. Medina, as he'd asked her to call him in school. He was very uncomfortable, almost squirming where he stood behind the headmaster. He felt Diana's stare, and looked up at her. He nodded, and in return received a blank look from his daughter.

'Well, Dad knows something. And I know that I know something, too, but what?'

The headmaster rambled on. "Anyway, what I'm saying is, we have high standards. You were accepted here, so you meet them. If for some reason you don't meet them in the future, you will be put on academic probation."

'That hair, that face, I know it! It's someone from a picture, a picture Rory showed me. I know, I KNOW!'

Max was turning green, now. Then Diana knew.

'Tristan! It's Tristan DuGrey! Tristan DuGrey that Rory was telling me about before I started at Chilton. He called her Mary, like Virgin Mary, and she rejected him, and…and Oh my God! Tristan DuGrey from the pictures, Rory's pictures. Rory's secret pictures. Those pictures she was hiding from Jess. Oh my God, it's Tristan DuGrey! Headmaster Tristan DuGrey.'