Disclaimer: I do not own the characters from Gilmore Girls as they belong to Amy Sherman Palladino and the WB. I have borrowed the story title from an episode of almost the same name. Oh and I don't own My Best Friend's Wedding which was quoted in the summary. Really people.

Rating: PG – 13

Part: One of two.

Dedication: To everyone who encouraged this fic when they shouldn't have. You know who you are.

Author's Note: I feel like I should explain why I wrote this when I have so many fics. But I won't.

Sometimes new love comes between old friends…

-- Reality Bites

Somewhere between college and the real world, I fell in love.

Well, stumbled into love is more like it. I figure that when you love, as passionately and unrealistically as I did, you won't fall in love – you'll stumble into it. You'll stumble and trip and fall flat on your face, not really knowing how you got there in the first place.

It crept up on me, even though it had been gradually building up inside of me since I first met him. Kind of like the pile of laundry that accumulates in my mom's room sometimes and then she finds her self buried in dirty clothes when she trips over a pair of high heels that she left lying on the floor the day before. No matter how many times I tell her she'll really get hurt one day, she doesn't listen until she falls.

Huh, someone should have warned me.

This love took me by surprise and I hated it. Hated him. Flip side, same coin and all that.  I sort of did hate him in the beginning of our tumultuous…acquaintance. We never were really friends before. That came afterward - after his façade had dropped and my innocence had dimmed. Back then, if anyone told me that in the future that I would fall for him, I would have had an aneurysm or something equally pathological.

But Tristan DuGrey has a way of sneaking up on you and permanently rooting himself in your life whether you like it or not.

I was on my own, fresh out of Stars Hollow and he was back from military school in all his be-all-you-can-be glory. And he was going to attend Yale. At first, we kept our distance, trying to settle into our new lives, makes new friends and juggle all our work. But we saw each other more, shared a few freshman classes. Later, when he decided he wanted to minor in journalism we saw more of each other and he would seek me out for help in homework.

Much to my surprise, we became friends.

By junior year, he was one of my most trusted confidantes. We'd have lunch or dinner. We'd catch a movie, take walks, and spend time on the phone discussing anything and everything we could come up with. He came to Stars Hollow one Thanksgiving to meet my family. We did everything two people who were extremely close, who trusted each other and cared about each other would do. Once in awhile, I would even accompany him to his parent's house or to a party under the pretense of being his girlfriend or date.

Then, all of a sudden, I didn't want to pretend anymore.

I mean, he wasn't my type. Sure, I liked him and he was fun to hang out with but he was still…Tristan. There was still times when he'd bug the hell out of me, tease me mercilessly. There were times we'd have huge fights, hurting each other with words. I could still look at him and see the boy I knew in high school - the arrogance, the pride, the cockiness, and the smirk. That infuriating smirk.

Oh and I didn't even want to think of the women. Because there were lots. If high school was the minor leagues then college was Tristan's major league breakthrough. One would think that girls who got into Yale would be more sophisticated and smarter…more immune to his charm. Unfortunately, I had yet to meet someone who hadn't fallen under his spell. I had actually prided myself for my being the only one…until now, I guess.

Did I mention how much I hated this? 

He was the Pacey to my Joey. The Spike to my Buffy. The Patrick to my Kat, the Darcy to my Elizabeth…you get the idea. Given the way all those couples started and ended, I should have known. 

It was something straight out of a teen romance. Being a senior in one of the world's most prestigious colleges, I thought that I was past the angst and drama of first loves and relationships. I assumed that I had grown up from love triangles and running away from boys I had just kissed.

Looking back, those relationships all seemed to lack something essential. With Tristan, and the feelings that consumed me, that I was drowning in - they all seemed very, very real. It was that feeling where you looked at someone and just knew, without any reservation that they were the one.

I can remember the exact moment it hit me. I was complaining (or bitching) to my roommate (who had been studying for an exam) about the latest airhead to hang on Tristan's arm…a bimbo named Muffin or something and she got fed up, closed the textbook and fixed me with a death glare.

"Have you ever thought about why these women Tristan dates bugs you so much?" she asked, looking completely pissed. I knew from experience you didn't try to talk when Paris Gellar was that angry. But since she asked a question, I tried to answer. My mouth opened but no words came out. She sighed, grabbed the books off her desk and as she stormed out of the room she yelled, "Figure it out, Gilmore. You're a smart girl."

All of a sudden, I was Cher in Clueless realizing she was in love with Josh. Well, sans the fountain and romantic music. No, in real life, there is no soundtrack. There's just this moment where it seems like your world has shifted subtly off balance for a millisecond and then, it's just as subtly shifts back again but you're not the same anymore.

I lowered myself onto my bed, hands shaking and knees weak. I was in love with Tristan.

After that, I was a wreck. Finals were approaching, the workload was increasing, plans for the summer were being made, my mother was calling at odd times with news about my siblings' achievements and I was completely shaken up.

I denied my feelings first; hoping they were just not there. But two days after my epiphany, I ran into Tristan in the library and I couldn't fight it anymore. He greeted me with a smile, touched my arm in a gesture that was meant to be friendly like it had been a thousand times before but this time, it made me excited and dizzy and anxious all at the same time.

All my senses were in overdrive. His eyes seemed bluer, his laugh sounded sexier, he smelled of soap and cologne and my toes curled. His lips were more inviting and as he talked, I kept wondering how they would feel against mine. I kept trying to recreate our one and only kiss in high school in my head, trying to relive the sensation.

I was in love with my best friend and what did I have to show for it? One kiss, a lifetime ago at a party. A kiss that we agreed meant nothing.

Would that be the only kiss we'd ever share? I asked myself over and over again, fearing the answer was a big fat yes. Would I always feel the way I did in the library every time I saw him from now on?

Would I love him forever without him ever knowing, without us ever having a chance?

These questions were driving me insane. It was the scariest feeling for me to lose myself so completely in someone where all I could think about was what I would say when I saw him next, how I would act. I am not completely sure how I got through studying for my finals. Perhaps, I was on autopilot.

One night, during a study break, I was sitting in my dorm room and watching My Best Friend's Wedding to get my mind off of all my problems. A word to the wise: never watch a romance on screen when your own love life is in shambles. It can never end pretty. I was sitting with a box of Kleenex as I rewound the tape and watched a particular scene over and over again, crying my eyes out - the scene where Michael and Julianne are on the ferry.

"Kimmy says if you love someone you say it, you say it right then, out loud. Otherwise the moment just..." Michael tells her as the ferry passes under the bridge.

"Just passes you by," Julianne finishes as he trials off.

And there it was.

I couldn't just take this love sitting down anymore. I couldn't define my relationship with Tristan on how many times he smiled at me or laughed at my jokes or pulled me into a hug. Not anymore.

I wanted more. Needed it.

So I decided to do something about it.

"I'm going to tell him," I announced to Paris and our other roommate Raina Chambers, as we were getting ready for a party at a fraternity. Paris had met this guy and she was dragging the two of us there with her as she tried to get him to notice her. College life had loosened Paris up. Go figure.

"Tell who what?" Raina asked a little distracted with the zipper of her dress.

"Tristan," I replied calmly and looked at myself in the mirror. "I'm going to tell him how I feel. Tonight at the party. I realize it's not the most romantic of settings but I figured, what do I have to lose?"

"Uh, possibly one of your best friends," Paris pointed out, adjusting her peach bra strap underneath her pink dress.

Raina scowled at her as I felt all the blood from my face drain away. She was absolutely right. If I told him and he didn't feel the same way - we could never be friends again. Not like we were before.

"Honey," Raina drawled in her southern accent as she clipped her honey-blonde hair with a barrette. "Don't listen to her. I've been just dyin' to see you and that fine boy wise up and get together. Y'all carry on as if you're a couple, anyways. I say you tell him how you feel and let it go from there. It's a risk, dahlin, but it's worth taking."

"You're sure?"

"Paris and I tried getting our hooks in that boy and failed," she paused momentarily to grin brightly at a scowling Paris before she continued, "maybe third time's the charm."

The pep talk had been given and I walked to the frat house, a bundle of nerves. The music seemed so loud, the house seemed too crowded and the punch left a bitter taste in my mouth – I couldn't tell if it was from nerves or because it was spiked.

Then he showed up, girl dangling from his arm as he talked to his buddies. Seeing him reinforced my fear and I was ready to head for the door and leave when his eyes met mine across the room and he waved. I know it's silly, stupid and clichéd but he spotted me, grinned and for a single second, everyone else just…faded away.

"Well don't you look out of place," he teased at he approached me, taking the glass of punch out of my hand. I shuddered a little at the contact and then chided myself for being so jittery. It was just Tristan. "This stuff tastes like feet."

I laughed a little, suddenly feeling completely at ease. "Like you've ever tasted feet."

"What are you doing here, Rory?"

"I like parties," I deadpanned. He slung an arm around my shoulder. The butterflies were back. I closed my eyes as I took in the scent of his cologne and soap and before I could stop myself, I blurted out, "You smell nice."

He chuckled and squeezed my shoulder playfully. "Can't resist it anymore, huh, Gilmore? "

"Oh yeah, I'm dying to get you in bed tonight, Tristan." Which wouldn't be bad at all. In fact, my mind chooses that moment to daydream vividly about Tristan and me, in bed. I cleared my throat and tried to keep my voice as aloof as possible. "Where's the flavor of the week? What's her name, Bambi?"

"Bambi was last week," he replied, unruffled by my teasing. "Her name's Claire."

My eyebrows furrowed; he usually went after the ones named after food or something. "She sounds smart."

"That's 'cause she is," he answered with a withering look in my direction. "Pre-med."

For the first time in my life a girl that Tristan was dating intimidated me. It was disturbing and belittling and almost had tears stinging. Don't cry, don't worry and stay cool, I kept repeating too myself. I had known him longer, loved him in some way longer. It had to pay off, right?

"Sounds serious."

"We're just having fun," he replied with a nonchalant shrug. That was a good sign. Tristan and I always had loads of fun together. "She's very sweet."

Oh boy.

 Deep breath. One, two three…"Tristan, can we talk?"

"That's what we're doing, silly."

"No I mean, somewhere less…crowded. Privately," I said, placing a hand on my stomach to settle my nerves.

"I'm intrigued. Let's go see if we can find a room where people aren't screwing," he stated cheerfully and I swatted him on the arm. He led me up the stairs and Raina saw us, and gave me two thumbs up and look that said 'looks like someone's getting lucky'. I shook my head vehemently and she frowned. Tristan found a room that a drunken couple had just vacated and once we were inside, he locked the door behind him. "How much do you wanna bet that they don't remember they had sex in the morning?"

I made a face even though my back was to him. The room smelled of alcohol and stale sex and only made me sick. "I don't even wanna think about what happened in here."

"Of course not, Mary…so what did you wanna talk about?"

I turned to face him, fear a solid ball in my stomach, my pulse tripping and my heart hammering against my ribcage. It was just the two of us. The loud conversations muffled and the music only heard through the vibrations in the room. The reality of what I was about to do – the potential damage I was about to cause – hit me full force and I did the only thing one could do.

I stalled.

"How'd your finals go?" I asked lamely, wringing my hands together. Maybe telling him in the flow of normal conversation was the best way to go. How's the weather tomorrow? What ya doing this weekend? Oh I'm in love with you, by the way. Wanna go catch a movie? Hey, it could work.

He crossed the room, closing the distance between us and involuntarily, I took a step back. He didn't notice and continued to inspect the room, stopping at the mantle to look at a picture. "Ah, you know, great. As always."

"That's good."

"What?" he asked surprised and stopped in front of me. "No comeback about my arrogance. Not even a 'get over yourself, Tristan'?" He placed a hand on my forehead and looked at me worried. "Are you feeling okay?"

"Cut it out," I snap, a little on edge and he looks shocked. I give him an apologetic smile and run a hand through my hair. "Sorry."

Now he looks genuinely worried and tips my chin up between his forefinger and thumb. "What's bothering you, Ror? You know you can tell me anything."

It was the softness in his voice, the familiar look in his blue eyes and the earnestness in his words that soothed my fear, calmed my nerves. He had come to mean so much to me and I felt so much for him that I needed to just tell him. I wanted to know what it would be like when I told him and see his expression.

I took a steadying breath as I brought my gaze to his. Now or never. "I love you."