(Please review, and for all-time Gilmore Girls fans, please forgive the summary at the beginning! It gets better, I promise! Enjoy!)

(I do not own the Gilmore Girls franchise, only the new characters :)

Chapter One

Lorelai Gilmore sat in the middle of her living room floor, surrounded by seating charts and pictures of flower arrangements, because she was planning her wedding. As part owner of the Dragonfly Inn, she had planned many weddings. But Lorelai had never had a wedding of her own, even though she had a daughter who was twenty- one years old named Rory (short for Lorelai). Lorelai had had Rory when she was sixteen years old with her high school boyfriend, Christopher Hayden. As the daughter of two very conservative and wealthy parents, Emily and Richard Gilmore, Lorelai was expected to marry Chris. Lorelai had her own plans. After Rory was born, Lorelai took her daughter, left her parents' home in Hartford, Connecticut and started her new life in a small, quirky town called Stars Hollow.

Stars Hollow was full of very interesting, but very loving people who cared for and accepted them. Lorelai applied and was accepted for a job as a maid at the Independence Inn. She worked for sixteen years, working her way up from turn down service to head manager. Rory grew up during that time, and she and her mom were unusually close. They were best friends first, and mother and daughter second.

When Rory was sixteen, she was accepted to a very prestigious private high school after she had applied. It was very hard to get in to Chilton but she got in due to a 4.0 grade point average. Lorelai didn't have the kind of money it would take to pay the tuition, but she wanted this for Rory, even more than Rory wanted for herself (which was quite a bit). So she reluctantly asked her parents for the money. They were happy to help but there was a catch. Emily requested that Lorelai and Rory come over to have a weekly dinner on Friday night at Richard and Emily's home. Lorelai hesitated but agreed. Rory attended Chilton and graduated Valedictorian! She also was accepted to Yale, where she was currently editor of The Yale Daily News newspaper and in her senior year.

Lorelai and her colleagues from the inn, Sookie St. James, (head chef) and Michel Gerard (who was the rather rude French concierge) started their own inn, when the Independence inn burned down. Sookie and Lorelai bought the very run down and abandoned Dragonfly Inn and after a year of construction, it opened. Shortly after opening, the inn, Lorelai discovered she had a serious romantic interest in Luke Danes, owner of Luke's diner, the girls' favorite place to eat and hang out. After two years of running the new inn and a year of dating Luke, they were engaged and the Dragonfly was very successful,

Lorelai sighed as she moved up on to her sofa. She had wanted to plan this wedding a long time ago especially since it been postponed from its original date. Lorelai and Luke had a falling out over the fact that Luke had hid a secret from her. Six months before their scheduled wedding day, Luke had found out he had a daughter named April. His old girlfriend from twelve years ago, Anna Nardini, had neglected to tell him he had a kid. He hid this information from Lorelai for two months. When Lorelai bumped into April in the diner, it all started to spiral down and they ended up separating. Something sparked between them a few weeks later and they were back together and better than ever.

Lorelai sighed with frustration as she saw the mess of wedding stuff she had piled everywhere. She grabbed the cordless phone from its dock and quickly dialed Rory's number at Yale.

"Hello?" Rory answered.

"I'm fed up with wedding stuff. You do it." Lorelai whined.

"Well, hello to you too, Mom."

"Sorry but still. I am considering just ordering pizza and having the wedding in the diner." Lorelai said as her dog, Paul Anka, jumped up onto her lap

"That would be festive." Rory replied.

"It's so tiring." Lorelai whined again.

"What do you still have to do?" Rory asked.

" Well, everything is pretty much done except getting my dress, making your dress, and whether or not April is going to be in this wedding, I have no clue."

"April, in the wedding?" Rory asked.

"Yeah, Luke was talking about it. I mean she is his daughter and if he wants her to be in the wedding, I think it would be great." Lorelai said.

"Well, if she says yes, then there will be two bridesmaids right?" Rory asked.

"Yes," Lorelai answered.

"It would be nice!" Rory tried to encourage her mother's spirits.

"I know it would, I agree." Lorelai said. "But enough about that, what are you up to?"

"Well," Rory began. "I got a call from Headmaster Charleston today."

"As in from Chilton?"

"That's the one."

'What did he want?" Lorelai was intrigued.

"He asked me if I would consider being a Chilton Alumni Student Advisor. "

"Oh, so a C.A.S.A?" Lorelai joked.

"Mom…" Rory groaned.

"I'm sorry, go on."

"It is a new program they set up to help incoming freshmen and transfer students get acquainted to the school, to show them around and have a relatively recent Chilton graduate answer any questions or concerns. I think it is a good concept and I agreed to help." Rory explained.

"I only wish that they had something like that when you were there." Lorelai answered.

"I know which is why I thought it would benefit another student who maybe doesn't have a cool mom like you to get them through it." Rory laughed.

"Oh you are hilarious." Lorelai replied.

"Well I had better go, Mom. I am supposed to be at Chilton by noon after my morning classes."

"Ok, honey, good luck!" Lorelai replied.

"Love you."

"Love you too."

The next morning, Rory arrived at her former school. She was immediately nostalgic as she walked down the hallways lined with lockers towards the office. Almost six years ago it had been when she herself had started here for the first time, although nervous, extremely determined. It was the Gilmore way.

Rory found herself down a familiar corridor and she entered the Headmaster's office. Headmaster Hanlin Charleston looked up and grinned.

"Ms. Gilmore, welcome. Please do have a seat, won't you?" he acknowledged the leather chair in front of his desk.

"Certainly." She answered, sitting down and smoothing out her skirt.

"I just wanted to say how wonderful it is you have agreed to participate in our cause. Ms. Clara Bennett is the new student I spoke of on the phone, correct?" he asked. Rory nodded.

"Yes, sir."

"Well, before I introduce her to you, maybe I should give you a little background information." Headmaster Charleston pulled out a manila folder and skimmed through it. Rory was confused.

"Ms. Bennett received a full scholarship to Chilton due to her academic achievements and various other things. She recently turned sixteen and entering our sophomore class. Unlike most of the students here, she resides at the Hartford Children's Center and has since infancy. But I have met many a student who have grown up without a family and have gone on to do great things. You and Ms. Bennett have much in common: a love of journalism, of books. She is incredibly bright, not unlike yourself and I thought maybe you could be, well, a friend to her. Show her the school and get to know her," Headmaster Charleston explained. "And I expect this to work out better than Ms. Fairchild's visit to Yale."

"Absolutely, sir, I would happy to and yes, that was a horrible incident. Won't happen again." Rory agreed and the headmaster stood up, smiling.

"If you would follow me, I asked if she would meet me outside in the hall." He led Rory out of the stuffy office. Sitting silently on the bench and reading a thick novel, was a dark haired, slender teenage girl. She looked up at them and Rory was suddenly reminded of her mother. Clara Bennett could have been a teenage Lorelai, with her long brown hair and sparkling blue eyes. She immediately stood up and put the book in her purse.

"Ms. Rory Gilmore, may I introduce Ms. Clara Bennett?" Headmaster Charleston watched as the girls shook hands.

"Nice to meet you, Clara." Rory smiled.

"Likewise, Rory." Clara smiled back.

"Well I will let you two get acquainted. If you have any questions, my door is open." He graciously bowed out, leaving the two in the deserted corridor.

"Shall we go get some lunch?" Rory asked.

"That would be great." Clara replied.

"All right then, off to the cafeteria. Actually the food is pretty good, believe it or not." Rory said and Clara chuckled. Rory led Clara back up the hall until they reached the staircase. Clara grabbed Rory by the arm before they headed down them.

"Rory, did the headmaster tell you my whole long sob story?" Clara whispered. Rory shook her head,

"Not really, he just told me the basics and we don't have to talk about if you don't want to."

"No, it's okay. I just didn't want you to feel like you had to treat me differently because of it." She answered.

"I know, don't worry." Rory assured her. "So who is your favorite eighteenth century poet?" Clara lit up.

"You're a reader?"

"And a writer, for the Yale Daily News." Rory replied.

"Wow… that is amazing!" Clara was impressed.

"I bet you are too." Rory smiled and they entered the cafeteria.

Over the course of the afternoon, the two got to know each other pretty well. Discussing Chilton was the least of their conversation; they talked about their favorite authors, places in the world and their backgrounds.

Clara was only about four months old when her sixteen-year old mother left her at the Children's Center in Hartford. Her mother deserted her with a letter, stating she couldn't her take care of her daughter any longer. As a result, Clara had lived there her entire life. She had entered the Chilton Academic Competition and won a full-ride scholarship to the school after a remarkable essay on certain authors who inspired her and whose works motivated her to aspire to her greatest potential.

The two acquaintances walked about the campus, discussing the school and class schedules of course, but they felt a bond between each other, like that of two sisters who could talk about anything.

"So, do you have a boyfriend?" Rory asked Clara, who blushed.

"Well, you could say that… I have known him my whole life. James Andrews grew up with me at…well, you know. He already graduated high school and is trying to get a job working in the area. He acts and sings, and is rather good at it. He works at the local school, helping with their drama department but he is finding that incredibly unfulfilling." Clara laughed. "What about you? Any man won the heart of Rory Gilmore?"

"Logan Huntzberger…" Rory answered dreamily. "His father owns some of the biggest newspapers in the country and is incredibly wealthy, but Logan is desperately trying to get out of his father's business. His dad has him in London now…"

"I'm sorry, Rory." Clara said, looking at the sad expression on Rory's face.

"It's okay. He'll be back soon." Rory assured herself.

All of the sudden, the school bell rang and students in blue plaid uniforms streamed out to the parking lots and the bus stop.

"Thanks for today, Rory." Clara said appreciatively; she was ready to head for the bus herself when Rory was struck with an idea.

"How would you like to come Stars Hollow with me?" Rory blurted.

"Oh, you don't have to do that." Clara said, but Rory insisted.

"I want you meet my mom and Luke."

"If you're sure…"

"I am!" Rory smiled

"I would have to talk to the lady in charge back home." Clara reminded her. Rory pulled out the keys to her car and smiled.

"Lead the way."