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Chapter 1: Pilot

The jet landed on the private airstrip in Hartford at 6:42pm. Rory Gilmore was sitting in her seat—seatbelt still fastened—looking through the window at the dark sky.

It's been almost three years since she moved away and almost five months since her last visit to Hartford or Stars Hollow.

Her life has definitely turned out a little differently than she thought. She had no complaints though.

She graduated from Yale, with honours, a little over three years ago. Upon her graduation, she received an offer to be an International Correspondent for CNN. This was her dream. The only detail that had her hesitating was that she would have to move to Europe because that's where the job was based. Despite the distance from everything she has ever known, Rory readily accepted.

That, however, was just the tip of the iceberg.

A few weeks before she was set to depart, her paternal Grandmother—Francine Hayden—passed away due to breast cancer. Rory wasn't too saddened by this since she was not at all close to Francine and it was not a secret that they did not 'get along', however, Francine shocked everyone by naming Rory the sole heiress to the Hayden Family Estates and fortune.

Rory couldn't believe it much less comprehend it. Francine left a video of her wishes and in that video she explained that she wanted to make amends to Rory, and that she was proud of her. Francine also apologized for her actions at that fateful dinner many years ago and thanked her son, Christopher, for helping her see how amazing Rory was.

Rory felt a little awkward after hearing about this inheritance. She felt that this was her father's birthright, not hers, but he assured her that she would do great things one day and that she deserved it. Besides, he didn't need it; he was set for life, as well as Gigi, thanks to his Grandfather.

Lorelai and Luke broke-up half-way through her senior year due to irreconcilable differences and a few months after Rory left for Europe, Christopher and Lorelai announced that they were going to get married.

In the matter of weeks Rory Gilmore, the recent Yale graduate, became Rory Gilmore-Hayden, International Correspondent, billionaire heiress and part of one big happy family.

The news converges and paparazzi were overwhelming at first and hard to deal with especially since she was trying to make a name for herself in the Journalistic Community without using her name and wealth.

Keeping a low profile made for a difficult task since she would be forced to attend society parties and DAR functions by her grandmother whenever she was in Connecticut. Apparently, it was her "duty" as a Gilmore and a Hayden to make appearances.

Even so, Rory was living her dream. She had everything. Well… almost everything; the only thing she didn't have was a serious relationship—someone to love—but that was made painfully clear by her grandmother, who constantly tried to set her up with promising bachelors with good pedigrees and excellent futures.

Emily Gilmore simply would not accept Rory's "It's not the right time to get serious" excuse. All she saw was Rory's biological clock ticking away.

The last serious relationship Rory had was with Logan Huntzberger and that was three years ago. They dated for two years (on and off and on and then off). Emily was devastated when she heard of their break-up. All her plans of that spring wedding at Cape Cod and blonde-haired/blue-eyed great-grandchildren went down the drain.

Rory had dated several eligible bachelors since Logan, though. Some of them she met through her grandmother; Emily had even (inadvertently) set her up with Bible Boy, also known as Tristan DuGray. They went out on a couple dates but came to the realization that they were really just 'good friends' material.

Nonetheless, all the men she had dated in the past three years were similar: all handsome, come from good families, prominent lawyers/doctors/businessmen/actors/journalists, even a few shipping heirs, and all men that she couldn't see herself having a future with.

"Rory?" She was brought out of her thoughts as she heard Colin McRae—her good friend since college—call her name as he stepped further into the jet.

"Colin," she unbuckled her seatbelt and stood up as he came into view, "It's great to see you!" She moved closer to engulf him in a hug, "How are you?"

Colin smiled, his arms still wrapped around her, "It's been too long, Reporter Girl." He smiled, letting her go, "I'm great. How are you? Flight alright?"

"I'm good. Flight was good." She smiled, running a hand through her long brown locks. It was good to be back in Hartford despite it all. Close to her friends and family. She missed them when she was away, but that was life. She watched Colin stand there, hands in his pockets, shifting his weight from side to side, and she smiled; he looked on edge. "Colin, are you sure you're alright? You can't seem to stand still."

"I'm fine. Don't worry about me; I've been like this for weeks now." He paused, "I'm just a little nervous about my impending nuptials. The closer it gets the more nervous I seem to get."

Rory laughed, "Colin, Colin, Colin…" She shook her head mock-disappointment and then disbelief, "I still can't believe you're getting married next week."

"Well, believe it. You are after all the maid of honor."

"True, but I am still trying to knock some sense into my best friend and your wife-to-be. You'd think that someone as intelligent and rational as Paris Gellar would know better." She joked.

"Yeah, yeah… Well you can enlighten her about the error of her ways over dinner," he looked down at his watch, "Which we are going to be late for. The car you asked for is waiting." He ushered her to get her stuff and she just laughed. Colin would never change. He would always be the neurotically punctual one of the group.

She picked up her LVCabas Mezzo bag and followed Colin off the jet. She thanked the pilot, and then the resident flight attendant for getting her trunks and suitcases into the waiting car.

"So, where are we going?" She asked once they were settled in the car and on the highway towards the city.

"Azul's," he said.

She nodded in approval, "Mexican, yum. Who's going to be there?"

"Just the gang," he paused, debating whether to list the company, but with the look of expectancy on Rory's face he decided to divulge it, "Lane and Zack are still on tour in California," Rory nodded, "So, it's just us, Paris, Steph, Finn, Tristan, and..."

"And?"

"Logan."

"Oh." She slightly paled at the mention of his name, but the darkness hid the fact.

"He just moved back from Seattle a few months ago, and he just got back from his trip to Washington yesterday, so Finn decided to invite him. Kill two birds with one stone, you know." He explained.

Rory slowly nodded, she couldn't seem to formulate actual words, never mind sentences. Her mind was furiously trying to process Colin's words.

They broke up a couple days after his sister's Wedding; it wasn't necessarily because of the events that happened at the wedding; it was just the beginning of a slippery slope.

She hasn't seen or heard from Logan since his graduation, when they said their goodbyes and he moved away to London for a full year.

It wasn't a bitter break-up, per se but it definitely hurt Rory—more than she thought was possible and more than she let the outside world believe—to watch him leave and never look back; after all, Logan was her first real love.