A/N: Hey guys! This is my new story. Been thinking a lot about some different theories ever since AYITL came out and I have been playing with this story in my head for a while and finally it started to come together.

Hope you enjoy it!

Prologue

When Lorelai Gilmore was 16 she was in love with Christopher Hayden. 3 weeks before her cotillion, she found out that she was pregnant. They were married immediately. They moved into her parents' house while they finished school. Christopher went to Princeton and followed in his father's footsteps and Lorelai spent time with her mother learning the life of society. The distance was a strain on their marriage, but they made it work.

After college, Christopher returned to Hartford, where he bought a house for himself, Lorelai and Rory. They hired a cook, 2 maids and a nanny. When it was time for Rory to start school, she was accepted to Chilton and she immediately became best friends with Stephanie Vanderbilt.

When Rory was fifteen she found her first boyfriend. Tristin Dugrey. They spent every free moment they had with each other. Shortly after Rory turned 16, she remembered that she had a cotillion coming up. She asked Tristin if he would go with her and he agreed. It was now 3 days before Cotillion and her mom was in panic mode.

Rory walked into their house that day after school and found her mom in the dining room trying to make the final decisions for the event.

RORY POV

"Hey mom." I said as I sat down at the table. Esmeralda brought me a cup of coffee and sat it down in front of me.

"Hi hun. How was school?" She asked.

"Steph broke up with Andrew." Mom lived for the gossip at Chilton.

"What happened?"

"She found him making out with Paris during study hall." My phone beeped telling me that I had a new text. I open it. It's from Steph.

Steph: Guess who's at the coffee bean?

Rory: Orlando Bloom?

Steph: Tristin's here with Scarlett?

"What?!" I yelled.

"What's wrong?" Mom asked.

"Mom I gotta change and then I gotta meet Steph." I tell her.

"Everything ok?" She asks.

"No." I say as I run upstairs to my room to change. I throw on a pair of jeans and a shirt. Put my black boots on and grab my jacket. I grab my car keys and leave. I call Steph as I pull out of the driveway.

"Hey." She said when she answered.

"Still at the bean?" i asked.

"Yeah. They're in a booth in the back. You on the way?"

"Pulling in now." I say hanging up. I grab Tristin's jacket that he left in my car. I walk in and in the back corner in a booth Tristin and Scarlett are cuddling. I walk past Steph, straight to them and throw Tristin's jacket at him.

He looks at me. "What the hell Rory?" he says.

"We're done! I've had enough. Lose my number, don't come to my house and don't come to cotillion." I said. Then I looked at Scarlett. "He's all yours." And I walk back towards Steph. She hands me a cup of coffee. "Thanks. I need retail therapy."

We leave the coffee bean and head over to the mall. "Who's having a party tonight?" Steph asked.

"Madeline. Her parents are out of town. Wanna go together?" I say.

"Definitely."

Steph and I shop for a while and then we head back to my house to get ready for the party. When I pull into my driveway I see my dad's car. "This isn't gonna be pretty." I say. When we walk in, Esmeralda takes my bags. "Can you put these upstairs for me?" She nods.

"LORELAI LEIGH HAYDEN! " I heard my dad yell from the living room.

I looked at Steph. "Told ya." We walk into the living room. "Hey dad."

"What the hell happened?" he asked.

"He cheated dad."

"It is three days from Cotillion. Your mother is upstairs in panic mode. Your grandmothers heard about it from a member of the DAR."

"Dad! It's gonna be fine. Don't worry." I look at Steph and she heads upstairs to start getting ready. I turn back to my dad. "I will find another date for Cotillion. Gotta go." I said and i ran upstairs. When i walk into my room Steph is in my closet looking for something to wear. "Find anything yet?" I asked.

"No not yet. How'd it go?" she asked.

"Well he's pissed. Apparently one of the DAR ladies was at the bean. So of course, mom's freaking out. Gotta find a new escort for this thing." I said walking to my closet. Tristin was gonna be at this party, so I needed to look hot. I grabbed one of my short blue jean skirts and a backless tee. I threw on a pair of my jimmy Choo's and went to the bathroom. I grabbed my scrunch hair gel. When i walked back into my bedroom Steph was finishing up. "Well?"

She turned her head and looked at me. "Damn we look hot." she said.

I walk over to my closet and grab my leather jacket. "Ready?" We walk downstairs, and my dad is standing by the front door.

"No." He said.

"Mom!" My mom and my sister Gigi come running in from the dining room.

"bye girls." Mom said.

"Why can't I go?" Gigi asked.

"Because your 13." Mom told her.

And we left. When we got to Madeline's party, the party was already in full swing. We found Madeline by the bar. "Madeline." I said.

"Rory, hey." she said handing me and Steph a drink. "I wasn't sure if you were gonna come since -" She looked past me.

I turned around to see what she was looking at. Tristin and Scarlett. "Yeah well... his loss." I said turning back and taking a sip of my drink. "Now because of his stupidity I have to find a new escort for cotillion."

Madeline looks at me. "My cousin's in town. He goes to Yale. He and a couple of his friends are staying with me. My parents don't trust me. I'll go get him." She said and takes off across the room.

"I don't know about this." Steph said.

"It can't be that bad." I said.

"I hope not." A voice says from behind us. Steph and I turn around. "Hi I'm Logan."

Wow. He's gorgeous. "Hi." It's all I can say.

"Are you Rory?"

I shake my head. "Yes. She's Rory and I'm Stephanie. Rory Hayden and Stephanie Vanderbilt." Steph says.

"Hayden? Any relation to the judge?" He says.

"My grandfather." I say looking at his eyes. "On my dad's side. My mom's dad is a professor at Yale."

"Oh yeah...who?"

"Richard Gilmore. He teaches Economics."

"Yeah i know him and Emily. Their friends with my parents. My dad's name is Mitchum."

Steph and I look at each other. It's impossible. It can't be. "Huntzberger?"

He nods. "One and the same. Miss me?"

I hadn't seen him since 7th grade. His parents had sent him to boarding school. Last, I had heard he was in Switzerland. I hugged him. "When did you get back?"

"Yesterday. Dad said that I needed to quit goofing off with my friends."

"Yeah I know how that is." I say taking another sip of my drink.

"Rory...can we talk?" A voice said.

I turn to look, and I see Tristin standing beside me. "There's nothing to talk about."

He glances at Logan who looks at me. "Who's this? Your playboy of the week?" Tristin said.

"Tristin don't be an ass. Your drunk. Go home."

"We need to talk about earlier."

I finish my drink. "Okay. You wanna talk. Let's talk about the fact that you were supposed to give me a ride home and you blew me off and I had to walk the 5 miles home. Or how about the fact that you have cheated on me numerous times and then you act surprised that I break up with you when I catch you in the act. 3 days before cotillion!" I say as I feel tears start to run down my face and I turn away from him.

"I think it's time you leave." Logan says to Tristin. I feel Logan's hand on my shoulder. "Come on let me take you home."

"I have my car." I say.

"Good then I'll drive." he says taking my car keys.

Logan POV

I help Rory out to her car. I tell Collin to keep an eye on Stephanie. He was happy about that since he's always had a crush on her. We go over to the coffee bean so that she can try and sober up a little bit before I take her home. Her dad would be pissed if she came home drunk. I get her to a table before I go and order. When I come back she has her head on the table.

"Ror, you gotta drink this." I say.

She sits up and she looks at me. "How could I be so stupid?" she asks.

"You're not stupid. He is." I tell her. I hate to see her like this.

We drink four cups of coffee and catch up on the last four years. I tell her about the 7 different boarding schools that I went to and she tells me about the drama that is Hartford and Chilton.

"So, cotillion?" I say.

" yeah Tristan was supposed to go with me but obviously that's not happening." she says.

"I'll go with you." I say.

She looks up at me. "Really?"

"yeah."

"Thanks." She looks at her phone since its buzzing. "It's Steph." She says and answers it. "Hey." she listens. "Be there in 5." She hangs up and looks at me. "I should go. Steph's waiting. Come by tomorrow." She says writing her number on my coffee cup and she walks out.

I quickly put her number in my phone and then call Collin. "Hey where are you?"

"Just dropped Steph off at Rory's. Where are you?"

"The bean. Come pick me up." I say and hung up.

On the ride back to Madeline's Collin and I talked. "So, you're taking her to cotillion. Just like that." Collin said.

"Yes. Just like that." Collin glares at me as we walk into Madeline's now empty house. "Don't look at me like that." We flop onto the couch where Madeline and her friend Louise are watching a movie.

"What're you guys talking about?" Madeline asks.

"Huntz, is taking Rory to Cotillion." Collin says.

Madeline and Louise both snap their heads over to us with their mouths open.