When Lorelai got pregnant at 16, it wasn't with Rory. It was with her older brother, James. Lorelai and Christopher got married. Christopher followed in his father's footsteps and became a lawyer. When James was two, Rory came along. They grew up in Hartford and went to Chilton Academy. They knew that when they got older, they would have responsibilities. James would be the Gilmore Heir and Rory would be the Hayden Heiress. They were the only two children of the Hartford elite that came from two prominent Hartford families. When James graduated high school, he headed off to Princeton. He and Rory both graduated valedictorian. Rory headed to Yale.

Chapter 1

Rory Hayden was sitting in her dorm room at Yale that she shared with her best friend Stephanie Vanderbilt. They were both freshmen along with their friends Logan, Colin, Finn, Robert, Paris, Madeline and Louise. Rory and Stephanie had been best friends since they were little. Stephanie had been there for Rory when she and Tristen had broken up after he decided to go to Princeton. Dynastic plans and all that. They all knew that their lives had been planned since their birth. Rory however was different. Rory's mom wasn't like the other Hartford moms, I mean after all she had Rory when she was a teenager. This being said, all of Rory's friends thought that her mom was the cool mom. When they were in high school, Lorelai was the one that they called when they was to skip school, or even if any of them were too drunk to drive. Lorelai was the one that Stephanie called the night that she found Rory on her front porch during a really bad snow storm. That also happened to be the night that Rory and Tristen broke up.

Rory was sitting in her room working on her Philosophy notes she heard a knock on her doorframe. She looked up to see her best friend and roommate. "Hey what's up? I thought you had a late class today." Rory said.

"It got cancelled. Listen, umm we were all talking about the Yale - Princeton game coming up." Steph said, causing Rory to glare at her. "Ror, don't look at me like that. It would be a good chance for you to talk to him."

"How do you even know that he's going to be at the game?" Rory asked.

"Because I just do." Steph said. "I'm going to meet Colin and Logan at the pub, you wanna come?"

Rory POV

I needed a break. "Yeah, let's go." I said standing up and following Steph out of the dorm. "You talked to him, didn't you?"

"He called. Sounded depressed. Asked about you." Steph said.

"He has no right. He's the one that broke up with me because he didn't want to do the whole long-distance thing." I said.

"He said that he wants to talk to you. He just doesn't think that you'll answer your phone." Steph said.

"I'll think about it." I said. As we walked to the pub, I couldn't help but wonder, was he regretting our break up? I was pulled out of my thoughts when I almost walked into a door. When we walked into the pub it didn't take us long to find Logan and Colin. "Hey guys." I said as we approached the table.

"What's wrong Ror?" Logan asked me.

I glared at Steph. "Steph's been talking to Tristen." I told him.

"What?" Colin and Logan both said.

"You said that you were going to stay out of it." Colin said to Steph.

"What are you talking about Colin?" I asked. Silence. Oh my god! I couldn't believe this. I turned to Steph. "Why? Why would you do this?" I asked her.

"Because you both have been so sad, it's obvious that you miss each other." She said.

"I can't believe you." I said and turned and walked out of the pub. I headed back to the dorm. When I got to our hallway, I saw someone standing by our door. I guess they heard me coming because they turned around. Tristen. "What are you doing here?" I asked.

"I didn't think that you would answer my phone calls." Tristen said.

"Your right, I probably wouldn't have." I said. "You still didn't answer my question. What are you doing here?" I said.

"I needed to talk to you." He said.

I unlocked my door. "Come in. I don't need everyone hearing our conversation." I told him. Once we were inside, I shut the door behind him. I walked over to the coffee pot and started it. Once I started it, I kicked my shoes off and walked over to it and sat down. "So…talk." I said.

Tristen walked over and sat on the other end of the couch. "I've been talking to Steph." I glared at him. "And…she's kinda made me see that maybe I overreacted to the idea of a long-distance relationship. Ror, I miss you. I miss you like crazy."

"Stop. Don't. You can't do this." I said. I stood up and started pacing around my common room.

"Why not? Steph said you're not dating anyone. C'mon Ror, you know that we're meant to be together."

"No. We were. Past tense. You ruined all of that when you said that you couldn't do a long distance relationship. I gotta go. Steph's at the pub." I said, putting my shoes back on, grabbing my keys and walking out the door.

I made the hour drive to my childhood home in Hartford. I couldn't believe this. Steph…my best friend, had gone behind my back and conspired with my ex-boyfriend to try and get us back together. When I pulled into the driveway, I saw that the lights were still on. Hopefully, my mom was still up. I walked into the house and made my way into the living room. "Hey mom." I said sitting on the couch across from her and my dad.

"Hey kid. Did we know you were coming home tonight?" Mom asked me.

I tossed my keys on to the coffee table. "No, it was spur of the moment." I said. I noticed that my parents gave each other a look. "What?"

"Nothing, kiddo. It's just that you don't usually come home spur of the moment…or on Thursday for that matter." My dad said.

I rolled my eyes. "I just had to get out of there for a while. Okay?"

"Sure sure." Mom said. The three of us sat there in silence for a few minutes. "So, are you going to the Princeton-Yale game?" Mom asked.

"Oh god. Not you too." I said.

"Rory, I think it would be good for you." Mom said.

"Would it also be good for me to go back to my dorm, where my ex-boyfriend is probably still waiting to finish a conversation about us breaking up?" I asked.

"Tristen's at your dorm?"

I nodded. "Yep. Apparently, him and Steph were talking about me and she told him how all I did was study."

"Oh kid."

"Yeah I know." I said, and noticed the look that Mom had. It was the same look that she had that time when I told her that my period was late and that I might be pregnant. Thank god I wasn't. "Fine, I'm going. I'll meet you at Grandma's for dinner tomorrow." I said grabbing my keys and heading back to school. When I got back to my dorm, I was right. Tristen was still sitting on my couch. "Your still here?" I asked.

"Yeah. I know you. You needed time to process. You probably went home too." Tristen said. He was right he did know me.

I walked over to the couch. "Tris, I know that you're looking for some kind of answer, but I don't have it. We broke up because you didn't want a long-distance relationship, so unless you're telling me that your transferring to Yale…I really don't see a different solution." I said. I walked over to the coffee pot and poured us each a cup of coffee. I walked back over and handed him his. I sat back on the couch.

"I'm not transferring." He said.

I nodded. "Listen, it's late. You can crash on the couch." I said, and he nodded. I stood up and started towards my room. "Just give it time Tris. The future has a way of working things out." I told him before walking into my room and shutting the door.

Logan POV

When Rory stormed out of the pub, I turned to Steph and glared at her. "What?" She asked.

"You. You said that you weren't going to get involved." I said.

"I know. But I couldn't help it. They were both so sad." She said.

"Steph! You just pissed off your best friend and roommate!" I said. I gave her a minute to let that sink in.

"Oh my god!" She said.

"There it is." Colin said, and I nodded.

"What have I done?" She asked.

"You need to go talk to her. You know what happened the last time that she froze any of us out." I said, remember when Rory froze Steph and James out for a month.

***FLASHBACK - 2 YEARS AGO…CHILTON HALLWAY***

Rory and I were sitting in the cafeteria, waiting for the rest of our friends and her brother James. I couldn't help but notice that she looked sad. "Hey you okay?" I asked her.

"Not really. Tris and I broke up last night." She told me.

They had been together since freshman year. We all thought that they'd be together through high school and college and then they'd get married. "What happened?" I asked.

"He's going to Princeton. Doesn't wanna do the whole long-distance thing." She said. "I'm so stupid."

"Ror, you're not stupid. C'mon. You'll be at Yale with all of us. I'm sure there's a guy out there that's perfect for you and that'll understand you and our life." I said. I wanted to tell her I had liked since before her and Tristen had started going out, but I couldn't. At least not the day after they had broken up. I would need to give her time. Time to get over him.

"Yeah I guess." She said, looking around the cafeteria. "Where is everyone?" She asked.

"I don't know, why don't we go find them?" I asked, and she nodded.

We walked out of the cafeteria and started down the hallway towards where our lockers were and saw a group of people standing in the middle of the hallway. We walked over to see what's going on.

"Have you lost your mind?" Paris asked Steph.

"It's not that big a deal." Steph said.

"She's not gonna see it that way." Mads said.

"I'm just gonna tell her." James joined in.

Rory pushed through the crowd. "Hey what happened to you guys? We waited for you." She said. Everyone got quiet. "Guys?"

"Steph and I have been dating." James said.

"What?" Rory asked quietly.

"We've been dating."

I could see Rory's face turning red. "How…long?" She asked.

"six months." Steph said.

She turned to James. "I can't believe you." Rory said. "I need to get out of here." She said and pushed past her brother. I didn't stick around. I followed Rory. She didn't need to be alone right now.

I followed her out to the parking lot, where she was getting into her Mustang that her parents had gotten her for her birthday. "Rory." I said.

"I can't be here right now." She said.

"Okay, well I don't think that you should be alone right now." I said.

"Well, you coming or not?" She asked, and I climbed into her car. Rory drove out of the parking lot. I wasn't sure where she was going. She just kept driving.

"Where are we going?" I asked after about ten minutes.

"I don't really know. I just know that I couldn't stick around. I mean why would James do this to me? She's my best friend. Why couldn't he have dated Summer or even Paris. Why Steph?" She ranted.

"I don't know, Ror. Why do any of us like the people that I do? I guess he probably felt the same way when you started dating Tristen, didn't he?" I said.

Rory laughed. "No, James hates Tristen. He does think of you as his best friend though." She said.

Really? I found this hard to believe. I mean, yeah, James and I had been close in middle school but not so much in high school, especially since we all had started dating. "So now what?" I asked Rory as she pulled into the parking lot of China Garden.

"Now? I don't know. I mean, it's done. I just need some space. From them, from Tristen." She said.

"From me?" I asked.

She looked at me and smiled. "You? Never."

She froze them out for three weeks. The only reason that she even started talking to them again was because we all made plans together for prom.

***END FLASHBACK***

When I left the pub, I headed towards my dorm room that I shared with Colin. It was highly likely that he had Louise there. They had been almost inseparable since they started dating just before school started. I was almost to my dorm when my cell rang. I pulled my phone out of my pocket. I smiled when I saw that it was Rory. I answered. "Hey." I said.

"Hey, are you still at the pub?" She asked.

"No, I was almost to my dorm. You okay?" I said.

"I don't know. Can you come over?"

"Sure. It'll take me like five minutes."

"Okay. Come to my window." She said.

"Alright. See you soon." I said and hung up. There was only two reasons that Rory would ask me to come to her window. One: Steph had company or Two: Tristen was there and she didn't want him to see me.

I made my way over to her dorm and went around to the side where her window was. She already had it open. I climbed in. "Hey." I said, as I closed the window behind me.

She was sitting at her desk. I walked over and sat on the edge of her bed. She turned and looked at me. "Hey." She said.

"So, what's up?" I asked.

"Okay, so I get back from the pub and guess who's standing outside my door." She says.

"Let me guess…Tristen?"

"Yep. Said that he drove out her to talk to me."

"About what?" I really hoped that he hadn't come to try and win her back.

"Apparently, he wants to get back together." She said.

"Wow."

"Yeah. So, I ended up storming out and driving home to talk to my mom."

"So, what're you gonna do."

"I'm not getting back together with him. I've been trying to move on and get over him. You know that." She said.

"Yeah. Just making sure." I said.

She smiled at me. "So, how was your day?" She asked.

"It was okay. I walked into the daily news earlier and my father was there." I told her.

"Why?" She asked and then saw the look on my face. "Wait. Never mind, it's Mitchum. There is no reason." She said.

"Exactly. So, he told me that my Mom's hosting a gala for the garden society and my presence is mandatory." I said.

"Wow. Need a date? You know that your mom loves me." She said.

Hmm. That was a thought. It could actually be what I needed to tell Rory how I felt about her. "Sure. You have a dress?" I asked.

"No, but I have my black card. When is it?" She said.

"Saturday night." I said.

I hung out with Rory for a little while and she even had me look at her philosophy paper that was due the next day. When I left Rory's, I headed to my dorm. I needed to call my mom and let her know that Rory would be coming with me to the gala. This had to be a good thing, right? Rory had never actually volunteered to go with me to a party.