Olivia was a 'big' girl to say the least and that was okay, because she was fine with her weight. She made peace with it. She knew that she was always going to get overlooked in favor of Rory, who was skinny.

Rory had this doll-like look about her that was definitely eye-catching in a good way.

Olivia...got looks...just not in a good way.

People look at Lorelai, then at Rory and go 'oh, so cute' and then they look at Olivia and then at Lorelai, then back at Olivia and then accusingly at Lorelai, eyes wide.

So, Olivia got used to the looks. Far used to them. She knew that she was just going to be overlooked in favor of Rory.

"Lost?" asked a man as Rory and Olivia awkwardly stood to the side.

No, we just like looking around, looking lost, Olivia thought. She can see other Chilton students looking at her, clearly thinking, Our school uniforms can get that big?

"Oh, yeah," Lorelai replied. "Uh, we're looking for the headmaster's office. The Ambroise building."

"Ah, okay," the man replied. "Well, this is it, right here. You just go inside, down the stairs, make a left, and the headmaster's office is at the end of the hall."

"Great," Lorelai said. "Thank you."

"You're welcome," the man said.

Rory grabbed Lorelai's arm and they tried to walk away, but the man extending his hand, clearly having other ideas.

"Um, I'm Ian Jack," the man said. "My daughter, Julia, goes to school here."

Lorelai shook his hand, "Hi. I'm Lorelai Gilmore. Um, these are my daughters, Rory, and Livi."

Ian looked surprised, "Your daughters? Really?" He looked at Rory then at Olivia and then at Lorelai, then back at Olivia, then back at Lorelai, looking a little baffled.

Olivia wasn't surprised. Ian was clearly thinking, What did you do to her?

Lorelai, seeing the slight judgment, put her arm around Olivia's shoulders, "Yup." She gave Olivia a slight squeeze as reassurance, "My daughters."

"Wow, that's great," Ian said. "Uh, I mean, daughters are a great thing."

"We're big fans," Lorelai said, grinning. "That's why I had twins."

"Yeah, uh, yeah," Ian replied. "So, is your husband here? I'd love to meet him."

"I'm not married," Lorelai replied.

"Ah," replied Ian.

"I'd love to meet your wife, though," Lorelai told Ian.

Ian said, "I'm divorced."

"Shame," replied Lorelai, clearly not finding that a bad thing.

"Yeah," said Ian.

Rory cut in, "Excuse me. My sister and I really gotta..."

"Right!" replied Lorelai. "We gotta go meet the big guy and I gotta, uh, get back to work."

They started heading away but Ian had other ideas, "Oh, where do you work?"

Lorelai walked back to Ian, "At an inn. The Independence Inn. I run it."

"Really?" asked Ian, taking in Lorleai's outfit.

"In a different outfit, of course," Lorelai replied.

Ian laughed, "Well, it was nice to meet you, Lorelai." He looked at Rory and Olivia, "Good luck in school, Rory, Livi. I'll tell Julia to look out for you both."

It'll be hard not to notice you. Especially you, Olivia was sure that Ian mentally added.

"Great, thanks," Rory said.

"See you," Ian added, before walking away.

Lorelai stared after Ian, smiling to herself. "What a nice, nice man."

"He wasn't that good looking," Olivia told Lorelai.

"Don't ruin it, Ollie," Rory said to her sister, "She's feeling pretty good about herself right now." To Lorelai, she added, "Aren't you?"

"Yeah," Lorelai said, still grinning rather stupidly.

"Do you want me or Ollie to get you a mirror?" asked Rory.

Lorelai stopped smiling, "I'm back. Let's go." 

They headed inside the building.

Oh, great. Stairs.

Rory asked Olivia, "What are you thinking?"

"Oh, great. Stairs," Olivia replied. She didn't want to walk down the stairs in case guys sat on the stairs to look up girls' skirts, like some guys did back at Stars Hollow High. Then again, she was safe. She was fat and no guys liked fat girls.

"I was thinking 'oh, good, more big stuff,'" Lorelai said.

"And I fit right in with the 'big stuff,'" Olivia muttered.

"You're not that big," Rory told Olivia, taking her arm in hers and heading down the stairs with her.

They passed by three skinny girls. From what Olivia had seen, she was probably the only curvy girl in this school. With some hope, she might slim down while attending Chilton.

The thing was, while Lorelai and Rory can eat a lot of food without gaining weight, it seemed like Olivia found it, putting on weight that she didn't want.

Emily and Richard had quite the surprise when they saw Olivia, because at Christmas, last year, she had been slim. She had just randomly started gaining weight and she found comfort in Sookie, who was just curvy as Olivia.

"Turn left," Rory said as they turned down a hallway and walked towards the double doors where the headmaster's office was at.

They stood outside the double doors.

"You two ready?" asked Lorelai.

"No," Rory and Olivia said in unison.

There was a moment of silence.

"You two ready?" repeated Lorelai.

"Yes," Rory said, and she and Lorelai pushed open the doors and walked into the office. They went up to the desk where the secretary was working at.

Lorelai cleared her throat, "Um, excuse me." The secretary suddenly looked up at her, making Lorelai jump back slightly in surprise. "Oh! How...wow, hi. I'm Lorelai Gilmore. These are my daughters, Lorelai and Olivia Gilmore...I named this one—" she motioned to Rory, "After me. I was the hospital all whacked out on Demerol. This one's dad—" She motioned to Olivia, "Named her after Olivia Newton-John. He had the biggest crush on Sandy, who she played in, in Grease, so he named his daughter after Olivia Newton-John, because he was a big fan – never mind. Um, but we call them Rory and Livi. It's short for Lorelai and Olivia, but they'll answer to either one, or even 'hey, you' or 'hey, stupid' depending on the—" Rory nudged Lorelai, "Uh, is the headmaster here?"

The secretary stood up, "One moment." She walked through a door that was behind Lorelai, Olivia, and Rory.

Lorelai whispered to her kids, "See? That's what happens when you go to bed with your makeup on."

The door opened and the secretary said, "Headmaster Charleston will see you now."

"Great, great," Lorelai said. "Thanks."

They went into the headmaster's office.

"Ms. Gilmore," Headmaster Charleston greeted as he shook her hand. "I'm Headmaster Charleston."

"Hi," Lorelai greeted. "Wow, it's really nice to meet—" She noticed Emily, "Mom." She spoke to the headmaster, "Um, excuse me." She went to Emily, "What are you doing here?"

Emily walked over to Rory and Olivia, "I came to wish my granddaughters luck on their first day of school."

Lorelai started, "But—"

"Rory, Livi, you two look wonderful in that uniform!" Emily told her granddaughters.

"Uh, you didn't have to come all the way out here, Mom," Lorelai told Emily.

Olivia was sure that Chilton was a five-minute drive from her grandparents' house.

"Well, this gave me a chance to make sure that Hanlin here takes good care of Rory and Livi," Emily said to Lorelai.

Lorelai looked at the headmaster, "You're Hanlin."

"Hanlin Charleston," the headmaster replied.

"Hanlin's wife and I are on the symphony fundraising committee together," Emily told Lorelai.

"Wow, that's great," Lorelai replied.

The headmaster spoke to Lorelai, "Your father and I are golf rivals. We're still fighting it out to see which one is worse."

"Oh, yes," Emily replied. "We're all old friends."

"Well, there's nothing like friends," Lorelai said. "Especially if they're old...ones."

Olivia hung her head slightly in embarrassment at that.

The headmaster spoke to Lorelai, "Well, would you like to take off your coat and have a seat?"

"Oh, no," Lorelai said, "No, I'm fine."

"I'm afraid they were a little overzealous with the furnace this morning," the headmaster said. "It's quite warm in here."

Olivia looked at the roaring fireplace. If the furnace was on overly high, why did he have a fire going? It made no sense.

"I like it warm," Lorelai replied.

"Lorelai, take off your coat and sit down," Emily chided. "You don't want Hanlin to think you're rude."

Olivia thought it was rather rude of Emily to say that.

Lorelai reluctantly took off her coat and gave an embarrassed smile at her outfit. "Laundry day."

"Hanlin, did you know that Rory has 4.0 grade average, and that Livi was on her varsity volleyball team?" asked Emily.

The thing was, Stars Hollow High was a very small school and there weren't enough students to form a junior varsity team and a varsity team.

It probably explained why their school teams sucked so much.

"I'm sure he does, Mom," Lorelai told Emily.

"They are very special girls," Emily told the headmaster. "You take good care of them."

"We'll do our best, Emily," the headmaster told Emily.

"Oh, god. Rory and Livi aren't gonna be problems. They're totally low maintenance, you know, like a Honda. You know, they're just easy, just...nice office," Lorelai said.

"Well, I don't think we should take up anymore of your precious time." Emily told the headmaster, "Hanlin, it was lovely to see you. Give Bitty our love."

 "Tell Richard I'll see him at the club Sunday," the headmaster told Emily.

Emily spoke to her granddaughters, "Have a wonderful day, Rory, Livi. I want to hear all about it." She spoke to Lorelai, "Do you need a ride or is your horse parked outside?"

Olivia tried not to smile at that jab, because it was funny, even if she didn't like the way Emily was rude to Lorelai.

When Olivia was nine, she wrote a letter to Emily, which basically went: "You are mean – mean - mean to my mom, like an evil machine." She obviously never sent it, and years later she found it in her closet when she decided to clean her room.

Lorelai spoke to the headmaster, "It's so nice to meet you." She spoke to Rory and Olivia, "Have a great day." She kissed them both on the forehead and started to head out.

"Oh, you don't want to forget your coat," the headmaster told Lorelai.

Lorelai doubled back, "Oh, no, 'cause that would be embarrassing." She grabbed her coat and walked out of the office with Emily.

After the two women left, Headmaster Charleston started going through the transcript folders.

"You're obviously bright girls," the headmaster said.

"Thank you," Rory said.

"Good grades, the teachers like you," the headmaster continued. He spoke to Rory, "Not a lot of social activities, though." He looked at Olivia, "You, on the other hand, have started the Book Club, joined the volleyball team and work part time at Antonioli's."

"Oh, well, just living in Stars Hollow is kind of a social activity, actually," Rory replied.

The headmaster looked at Rory, "Nothing in your school and town appealed to you?"

Rory said, "I work at my mother's inn after school sometimes. And I was in the German Club for a while, but there were only three of us, and then two left for the French Club after seeing Schindler's List, so..."

"And even the teacher and the other two couldn't be bothered to show up to German Club on some days," Olivia muttered.

The headmaster looked at Rory, "What are your aspirations?"

"I want to go to Harvard and study Journalism and Political Science," Rory said.

The headmaster asked, "On your way to being?"

"Christane Amanpour," Rory replied.

"Really?" asked the headmaster.

Rory answered, "Yes."

"Not Cokie Roberts?" questioned the headmaster.

"No," replied Rory.

The headmaster asked, "Not Oprah, Rosie, or one of the women from The View?"

"No," replied Rory.

"Why do you wish to be Christiane Amanpour?" asked the headmaster.

"Well, I don't wish to be her, exactly," Rory replied. "I just want to do what she does."

The headmaster asked, "Which is?"

Rory explained, "Travel, us, see the world up close, report on what's really going on, be a part of something big."

"And to be part of something big, you have to be on TV?" Headmaster Charleston asked, "Why not lead the police on a high-speed chase? That's a quicker way to achieve this goal."

Did he just tell Rory to commit a crime? thought Olivia.

"Being on TV has nothing to do with it," Rory explained. "Maybe I'll be a journalist and writes or articles about what I see. I just want to be sure that I see...something." The headmaster looked down at Rory's papers, "You'll notice the debating team's also missing from the resumé."

The headmaster looked at Olivia, "And what are your aspirations?"

"I want to own a pizzeria someday," Olivia said. "I plan on going to Yale to study business."

"On your way to being?" asked the headmaster.

"Myself," Olivia replied. "I mean, I can always be somebody, but I prefer being myself. I don't want people to like me for being a carbon copy and I want people to hate me for being honest about who I am."

"In fact, I was at a party at their house just last week where I had the most delicious lobster puffs I've ever eaten." The headmaster added, "I'm very fond of them."

"I actually like the crab cakes," Olivia said.

"None of this, however, will be of any benefit to you. Chilton has one of the highest academic standards of any school in America. You two may have been the smartest girls at Stars Hollow, but this is a different place," the headmaster explained. "The pressures are greater, the rules are stricter, and the expectations are higher. If you make it through, you will have received one of the finest educations one can get, and there should be no reason why you should not achieve all your goals. However, since you are starting late and are not used to this highly competitive atmosphere, there is a good chance you will fail. That is fine. Failure is a part of life, but not a part of Chilton. Understand?"

Olivia leaned forward a little, "We understand, and we say, 'challenge accepted'."

The headmaster passed them their folders, "Takes these to Miss James in the administration office across the hall."

They took their folders and headed out.

"God, everyone in this school walks around like they have a stick up their ass," Olivia muttered.

After filling out a form, they were given their class schedules, map, the dining room, the science hall, and the theater. They were also given the Chilton Honor Code, the school rules, and the words to the Chilton song.

They went to Mr. Medina's classroom together and found some seats.

Now, Carter Holloway wasn't interested when regular students came in, but when two new girls walked in class together, he found himself curious.

Okay, they were pretty, he wasn't going to lie. The blonde girl had long hair that she put up in a scrunchy. She was also kind of chubby, but nothing to write home about.

The girl following behind her was definitely Carter's type: nice short brown hair, tall, with doll like features, with stunning blue eyes to go with that innocent façade.

The only thing that threw off the gorgeousness of the brunette was that ugly ass backpack she was toting.

The blonde girl sat in the empty desk right in front him.

She messed around with her floral backpack that Carter could see had pins in it before taking out some pastel notebooks and a blue pastel colored pen.

She zipped up her backpack and proceeded to hang her backpack on the back of the chair by the strap.

That thankfully gave Carter a better view of the girl's floral backpack and at the pins that she put on it.

Floral backpack, pink wristwatch, and pastel notebooks...this girl was unashamedly girly, apparently.

It was...oddly refreshing to see.

Some girls tried to rebuff the 'girly-girl' outlook under the guise of 'not like other girls.' Sure, he dated girls like that, but it was tiring of dealing with, especially when those girls put other girls down.

This girl in front of him seemed different.

He peered at the pins on the girl's backpack again. So far, his favorites had to be the 'Carrie White for Prom Queen', the 'Garbage Club, live fast eat trash', 'scream team, eat bread play dead', and the 'spooky book club' with accompanying ghost pin.

He looked at the brunette girl that the blonde came in with.

Yellow backpack, looking intimidated every time Paris answers the questions Mr. Medina was asking.

The brunette kept glancing at the blonde girl, who was busy taking down notes and doodling vines along the margin of her notebook.

Something about the blonde was intriguing as she seemed lost in her own world, even though she was taking notes.

Tristan walked in and the blonde girl looked at him, but didn't seem all that interested because she went back to her notetaking.

Someone who resisted the good looks of Tristan Dugray?

Now, this girl was clearly perfect.

"Who's she?" asked Tristan, looking at the brunette girl, only having eyes for her.

Carter felt irritated at that, because the perfect girl was sitting right in front of him. He corrected Tristan, "New girls."

The bell rang and Tristan looked between the blonde and brunette. He loudly said, "Looks like we've got a couple of Marys." 

The blonde girl turned around in her seat to look at Tristan and Carter, clearly wondering what the hell that meant.

But Carter's breath caught in his throat, because the blonde girl had killer blue eyes.