Rory & Riley

Disclaimer: I do not own Gilmore Girls. (With the exception of all 7 seasons on DVD.) I only own Riley.

Notes: Season 4 & beyond AU. Everything from seasons 1-3 still happened with the exception of Rory's relationship with Christopher. Christopher still got involved with Sherry and had Gigi. In this story, Lorelai had twins, Rory and her twin brother Riley (who is older by 10 minutes). After they were born, with Lorelai and Christopher not wanting to get married, everyone decided it would be best for each teenager and their parents to only be responsible for one baby so Christopher and his parents would raise Christopher Riley Hayden while the Gilmore's raised Lorelai Leigh "Rory" Gilmore. Lorelai of course eventually found her way to Stars Hollow to raise Rory away from Hartford Society and Christopher tired of his parents pressuring him to still attend Princeton took off to Boston to raise Riley on his own. Each child grew up in the image of their respective parent with zero knowledge of each other or their other parent. Also, in some chapters I borrowed dialogue directly from the episodes.

Background on Christopher Riley Hayden: He is basically the male equivalent of his twin sister. He is a lover of all things pop culture, a good book, and a really good cup of coffee. But he also got his parents rebelliousness and has on occasion got into trouble which resulted in a brief stay in military school.

Chapter 1: "Hi, I'm Riley!"

3 AM! Rory Gilmore couldn't sleep. She looked at the clock on her nightstand and couldn't believe the time, 3 AM! She had to be up in four hours to get ready for her first class and had gotten no sleep. She was exhausted after the party her roommate, Paris Geller, forced her to open the door for, not to mention irritated by the Olsen Twin wannabes her grandmother was trying to force down her throat. But despite all of that she could not get her body to just let her go to sleep. Figuring she was fighting a losing battle Rory decided to move to the common room she shared with her suite-mates to watch a movie, hoping she may eventually succumb to exhaustion on the sofa.

She was just about to start the movie when a light snore coming from outside her dorm caught her attention. Rory opened the door to discover a sight she never expected to see. Oh my gosh. He's naked! I wonder if he's okay. How long has he been out here?

Tapping the sleeping, naked guy on the shoulder with the tie from her robe, he woke up.

"I'm naked," he stated.

"Yes," Rory replied.

"I'm naked, I'm on the floor, and you're a girl, so I must be…" he said.

"On the wrong floor," she finished.

"I should probably find my room and my clothes. What building is this?" he asked.

"Durfee," Rory told him, "Which building is your room in?"


As he started to get up Rory stopped him, "hold on," she said and handed him her robe to put on.

Reaching out a hand to her he said, "Hi! I'm Riley."


As he walked away Rory surprised herself, "Hey, I couldn't sleep so I was just about to start a movie and have some coffee. Do you wanna join me? It might help the hangover. I've also got some sweats you can put on so you don't have to walk back to your dorm like that."

"What movie," Riley asked.


"One of my favorites. Coffee sounds good, too."

After handing Riley his coffee, Rory took a seat next to him on the sofa. "This is really good," he said.

"Not as good as Luke's," Rory replied.

"Who's Luke?"

"My mom's boyfriend. He owns a diner in Stars Hollow, where I grew up. He's basically like my dad since mine has never been around. They've had a thing for each other for as long as I can remember, but neither of them ever admitted it until my high school graduation. I included Luke in my "thank you's" for getting me where I am in my speech and I guess my mom finally realized not only how important he was to me, but her as well that she kissed him on the spot and they've been together ever since."

"Wow," he said, "take a breath already."

"Sorry. I have a tendency to ramble. I get it from my mom," she said.

"That's cool. So somewhere in that rant of yours I believe I learned you were raised by single mother and were valedictorian of your class. So besides a love of coffee and an appreciation for one of the greatest movies of all time, it seems we have a couple more things in common. I too, was raised by a single parent, but by my dad. And I have no idea who my mom is. She has never been around either. I was also class valedictorian."

"Okay, so you like to ramble, too. Good to know," Rory laughed, "where are you from?"

"Boston," he said, "but I've gone to school in North Carolina for the past two years. I graduated from Oak Ridge Military Academy."

"Military school? Was that by choice or were you exiled there?" Rory asked.

"A little of both, I guess. My dad's never had any significant relationships. It's always been the two of us against the world, but freshman year he met Sherry and a year later, along came Gigi."


"She's my half-sister; it's short for Georgia. Sherry's great and I love Gigi. I love seeing my dad so happy and growing up an only child to a single parent, I'd wanted a family. When I was little I dreamt about what my mother was like and my little sister, too. Cause for some reason my dreams always included a little sister. I would protect her from bullies, boyfriends, bad dreams. And in turn she would help me sneak out of the house if I wanted to go out and dad said no. When Sherry and Gigi came along I finally got the family I always wanted. Part of me was happy. I love them both and I'll protect Gigi with my life, but the other part of me resented the fact that Gigi was going to grow up the way I had always wanted, with two loving parents. So I started sneaking out more, going to parties, and coming home drunk I kept my grades up, so dad didn't have too many complaints, but in the end we decided Boston wasn't the right place for me. I wanted to go, but my dad decided on Oak Ridge. In the end it all worked out, though. I learned not to resent the things I didn't have, but appreciate all the things I did have and I made some good friends there. I actually met my roommate there. He had been exiled there by his father after some stupid things he and his friends had done. We were bunk-mates and eventually became the best of friends."

Rory wasn't really sure what to say. She definitely understood what he meant by resenting the things he didn't have. She felt the same way. Yeah, she loved her mom and Luke has always been the father figure in her life, but part of her still wondered who her father was and what it would be like to have him in her life. She also wished she wasn't an only child. As her best friend as well as her mother, Lorelai Gilmore has always been like a sister to Rory, too and so has her best friend Lane Kim, but she has always dreamt of having an older brother; the kind of brother who would look out for her and protect her like the older brothers did in a lot of movies and television shows she watched.

"You know I met my roommate in high school, too." Rory finally said, "I wouldn't exactly call her my best friend though. We're more friend-ish. We have a really strong tendency to push each others buttons, but at the same time we push each other to be the best. We work well together. It took awhile to get there, though."

"What do you mean," Riley asked?

"She used to hate me and for no other reason other than she was threatened by me."

"Why was she threatened by you?"

"I transferred to Chilton Academy in Hartford from Stars Hollow High sophomore year. It was the best place for me to get the education I needed to get me into Harvard."

"Wait, Harvard?" Riley stopped her.

"Yeah that was always the plan. I got into Harvard as well as Princeton and Yale, of course, but in the end Yale had the most "pros" so it won."

"I'm sorry, "the most pros." What's that?" Riley asked.

"It had the most "pro's" on my "pro/con" lists for each school. I make all my important life decisions with them. So anyway, back to Paris, that's my roommate's name, she was the top of the class and was going to be the editor of the school paper. She also had plans to go to Harvard as well and here I was the new girl coming in a month into the school year with glowing recommendations, top grades of my own, and a desire to be the next Christiane Amanpour. She hated to be challenged and felt I was one so she immediately hated me," Rory told him, "Of course, it also didn't help that the boy she had liked since first grade and had no interest in dating her took a weird liking to me."

"A weird liking?" Riley asked. "Tristan liked to annoy me. From day one he dubbed me the school's "Mary" and was relentless in his attempts to get me to go out with him. He was the "King of Chilton" no girl would dare turn him down, but I did so he made it his mission to get me to agree and since Paris liked him she hated me."

"Are sure he didn't really like you and not as a conquest or anything, maybe he actually liked you, but just didn't know how to show it," he asked?

"I guess it's possible. I never got a chance to find out, though. He, like you was sent to military school at the beginning of junior year. He made some bad choices with his friends. They did some stupid stuff and his dad pulled him out of school; on the night when he and I were supposed to perform as Romeo and Juliet, actually. I wound up having to perform with Paris as Romeo and believe me she does not kiss as good as Tristan. But, on the upside, at least after he was gone Paris didn't hate me as much so we were able to work on becoming friends," she said.

"So did you ever have feelings for Tristan? I mean, you did just say he was a good kisser." Riley asked.

"I don't know, maybe. There were times when we would have some decent conversations and he wasn't being his usual obnoxious self. The night he left school he told me he would have kissed me goodbye, but my boyfriend was there. A part of me was glad he didn't because nothing good could have come from him kissing me. My boyfriend would have beat the crap out of him and most likely broken up with me. Plus he was leaving so even if I liked him, it wasn't like it could go anywhere."

"What about the other part," he asked?"


"You said a part of you was glad he didn't kiss you. Was there a part of you that wished he did?"

"Yeah, I guess there was. We had kissed once at this party the year before and I wondered what it would be like to kiss him again. That night his girlfriend had just broken up with him, in front of the entire party by the way. I went to the party to avoid my feelings over having just broken up with my boyfriend at the time, Dean. We broke up the day before on our three month anniversary after he told me he loved me and I didn't say it back."

"Wow that sucks."

Rory laughed, "That's exactly was Tristan said. Anyway, I was bored with the party, but my friend that came with me was dancing with this guy she met so when I went to find a quiet room that I could read in I came across Tristan sitting at this piano. He looked so sad. I still hated him for the whole Mary thing and everything else, but somehow I found myself trying to cheer him up. We talked for a few minutes. He apologized for having been a jerk to me all year and the next thing I knew he was kissing me and I was kissing him back. And then I was running out of the room in tears.

When I found Tristan at school a few days later I told him I cried because I hadn't wallowed over Dean, yet. That was true, but in reality I cried because it was an amazing kiss. It was better than any kiss I had shared with Dean and it scared me. With that one kiss I felt more for him than I felt for Dean or every imagined feeling for anyone, but I was scared that I would just be 'one of the many' that I ended up telling him it didn't mean anything."

"That must have been some kiss." Riley said.

"It was," she replied, "and if I'm being really honest with myself it was the best kiss I've ever had. Before and since then, nothing and no one has compared. But, it's not like it really matters now. I haven't seen or heard from Tristan since he was sent away to military school and I doubt I'll ever see him again. I guess he was destined to be 'the one that got away' instead of 'the one'."

Chilton, Tristan, Mary? Riley couldn't help but wonder if this girl in front of him; the one whose dorm he just happened to pass out in front was the very girl who since he had known him had owned his best friend's heart. He couldn't believe it, after all the stories Tristan had told him about the girl that got away, never in a million years did he expect to not only come face to face with her, but discover that she had those same feelings. Oh, it was shaping up to be a great semester. Now he just had to find the right way to reintroduce them to each other.

They continued their conversation well into the early morning hours, completely forgetting about starting the movie, but instead just enjoying getting to know each other. Rory told him more about her relationship with Dean, then her relationship with Jess and what she knew about her other suitemates, Janet and Tanna. Riley told her about his ex-girlfriend, Sarah. They dated their first two years of high school until her family moved to California. Since then, he's gone on dates, but hasn't had a long term relationship.

They talked about their likes, dislikes, hometowns, friends, and their relationship with their parents. Neither could believe that anyone could be as close to their parents as they were. They also discovered they were both English majors and plan to join the school paper. As the sun started to come up Rory looked at the time, seeing that it was nearing 7 o'clock she knew it was time to say goodbye so she could get ready for her 8 o'clock class.

"So," she started, "as much as I hate to kick you out. I've got to get ready. I have my first class in an hour."

"No problem. Me too. What class?" Riley asked.

"English 10: A study of Jane Austen. She's my favorite author so I'm really excited about this class and I can't be late," she said.

"I don't blame you. I'm in that class, too. I love Jane Austen. I don't love her as much as Hemingway, but she is a brilliant author," Riley said.

"Ugh, what is it with guys and Hemingway. I just can't get into his stuff. I've tried, but he just puts me to sleep. So I guess I'll see you in class, then," Rory replied.

"I guess you will. See you later, Rory."

"Louis, I think this is the beginning of a beautiful friendship!"