Full Summary: Rory's life is perfect, until her boyfriend, Dean, breaks up with her. In an attempt to win him back, she enlists the help of Jess, her best friend. Their plan goes awry, however, when it becomes clear that her feelings for her friend, as well as his feelings for her, aren't as platonic as she thought.

A/N: First of all, credit where credit is due. The characters, and some of the scenes and bolded dialogue belong to Amy Sherman-Palladino, the incredible mastermind behind the Gilmore Girls series. The inspiration for this story came from the fan-made movie trailer, "Choices (#1)" on You Tube, made by popcan11. I've received permission to post this story, so everything's all legal and tidy. I'm really excited about this one! :D Hope you enjoy!

You know how some people brag about how wonderful their life is? They've got the looks, the job/school, the friends, the family life... everything just seems to be in the right place, and they've practically got the world in their hands.

Well, that's how my life was... until my senior year of high school.

The year started out great. I was Chilton's Student Body Vice President—after much cajoling (or demanding) from Paris, who was the President—and though I didn't have a lot of friends, the ones I had were real friends.

There was, of course, my mother, the one and only person whom I unabashedly idolized. She was my pal, my confidant, my true best friend. I couldn't picture life without her, and quite frankly, I didn't want to. It was just too painful.

Then there was Lane; she fit into the category of "Female Teen Best Friend." I could talk to her about almost anything. I went to her with most of my boy drama, though I often did tell my mother, as well, and we spent more time than I could measure in her room or mine, listening (very quietly) to all kinds of forbidden music, and talking about what was new in our lives.

And then, there was Jess. He was a new friend, compared to Lane and my mom, as he'd only been in Stars Hollow for a year. But he filled the "Male Teen Best Friend" slot perfectly. Like Lane, we had the same taste in music and books and such, but we also had some thoroughly enjoyable verbal spats that could last for hours. They never amounted to much, just some mild bickering between friends. And he never pressured me for details, when I happened to go to him when I was hurt or angry. He just listened to what I was willing to tell him, offered advice when I asked for it—which, it often turned out, was the best advice I'd get from anyone—and in general, he was just there. Sometimes that was all I really needed. And I was there for him, too, when he needed it. It was a very symbiotic friendship.

On top of these things, I was a beloved and prominent member of my town, and quite possibly the most ambitious and successful teenager that had ever lived there.

And then, there was Dean. Perfect, dependable, sweet, loving Dean. He had that tall, dark, and handsome thing going for him—standing at a rather intimidating six feet and two inches—and from the very beginning, he'd captured my interest, my breath, my heart. We didn't have a whole lot in common, but despite that, we had some good times. No, not like that, you perv. We went to a lot of movies, dinner, talking about nothing, and the odd make-out session here and there. And I was in the process of educating him, introducing him to Tolstoy and Björk and lots of other things that were big contributors to my person. I took my books, and my music, very seriously. But he seemed willing to learn, for the most part.

Everything seemed perfect, until the Stars Hollow Dance Marathon rolled around. My mom had been desperate for the "big, fancy trophy" for the last five years, and she was determined to win it this year. Her plan? Dance with me.

Joy.

Unfortunately, her logic, and her pouty, pleading smile were just too much for me to resist, so I reluctantly agreed. And now, I was really starting to regret it. We were in the lavishly decorated gym at Stars Hollow High, and I was pretty sure I'd lost all the feeling in every single one of my toes. My heels were only two inches high, for God's sake! How the hell does that work? Mom must have been dying, because her heels were way higher, and several years older. Yes, years. She bought vintage heels. And I was just waiting for the inevitable.

Glenn Miller's "In the Mood" echoed through the gym, the repeated motive lulling me into an exhausted half-slumber, while I still fought to move my feet. Mom's arm was loosely wrapped around my waist, and mine was draped over her shoulders, both of us attempting to stay upright. It was just barely working.

"Tell me a joke," she mumbled sleepily.

Really, Mom? Ugh... okay, think of a joke. Um... "Knock, knock."

To my surprise, she began giggling incessantly, swaying a bit as she did. "That's a good one," she gasped, and suddenly, I joined in her laughter. Neither of us had any idea why it was so funny, but we just couldn't stop laughing.

Then there was a snapping sound, and Mom gave a different gasp, nearly losing her footing. "You okay?" I asked.

"Oh, no!" was her reply. "My heel broke!" she announced, bending down to pick up the heel in question. "Damn, these are brand new shoes, too!"

I frowned. "They were made in 1943," I pointed out.

She gave a little pout. "Well, I just bought them Tuesday!"

"I told you not to wear vintage shoes." Ten points to me for being right.

"But the lady at the store said they hadn't been worn a lot!"

"Yeah, but not a lot in sixty years is still a lot."

Mom glanced frantically around the gym. "I gotta fix them," she said, then gasped yet again, this time excitedly. "I'll use my emergency card!" As she spoke, she reached into her cleavage—real classy—and produced the yellow ten-minute card all the dancers had been given. She started to move away. "I'll be right back."

That woke me up a bit. "No, stop! If you go, there's no way I'll be able to stand up on my own!"

"Ten minutes!"

I laid my head on her shoulder. "Nighty-night."

She sighed. "Fine." I was vaguely aware of her calling Dean over, and the next thing I knew, I was being pressed against a rock-hard chest. My mouth curled into a small, tired smile, and I snuggled closer. I could hear Mom persuading Dean to stay here, and I knew it wouldn't be long before he caved. Lorelai Gilmore was nothing if not a brilliantly persuasive individual.

After a few minutes, I opened my eyes to see how close Mom was to being done. In the process, two familiar faces caught my eye. The first was Jess, watching us both with an amused smile on his face. He hated these town shindigs, but I'd asked him to come and support me and my mom, so he had. He was a good friend.

The second face, however, I was less than pleased to see. It was Shane, Jess's flavor of the month. He had a lot of girlfriends, though none of them were serious. I'd liked most of them, though I never got too close to them, knowing she wouldn't be his girlfriend much longer. But I'd had the hardest time liking Shane. She was snotty, conceited, even more fashion-obsessed than my mother—without the flawless sense of style—and she seemed very clingy. She was always popping up unexpectedly, and fusing her lips to his. He didn't seem to mind, which was all the more frustrating and confusing. I knew Jess; I knew him better than anyone. I knew he didn't like it when girls were all over him. He liked personal space, he liked time to himself. So why was he letting her invade his bubble?

"Ugh, why did he bring her?" I muttered under my breath.

"What?"

I struggled to lift my head, looking Dean in the eye. "Jess brought Shane," I pointed out. "Why did he have to bring Shane? I can't stand that girl."

Dean sighed. "Just ignore her."

"Yeah," I mumbled, but my eyes inadvertently flitted back to them, just as Shane sat up straight, leaning over to Jess, who was lost in Ernest Hemingway. (A/N: I don't know if that's really what he's reading, but let's pretend it is, 'cause it sounds cool.)

"Oh, my God," I groaned, rolling my eyes. "I swear, she's all over him! What, is she just out of prison or something?"

"Okay, that's it!" Dean snapped, pushing me away. "I'm tired of this!"

I frowned. "What are you talking about?"

"You don't want to be with me, Rory!" he shouted. "Everyone can see it!"

"Yes, I do!" I could feel the tears threatening.

He laughed and shook his head. "No, you really don't. So you know what? I'm going to give you what you want. We're not together anymore, as of right now." And with that, he turned around, picking up his jacket and leaving the gym. I stood in silence for several minutes, staring at the place where he'd just been standing.

"Rory?" I heard someone call.

At that moment, the reality came crashing down on me. Before anyone could see my tears, I ran out of the school, toward the lake, and the bridge. I fell to my knees, not caring if I tore my pantyhose, and cried for I don't even know how long. When I felt like I had some control over myself, I scooted over on the bridge, swinging my legs over the edge. It was quiet, other than the occasional sniffle coming from myself.

I spotted movement in the corner of my eye, and glanced at the calm, reflective surface of the lake. Jess strolled across the bridge to where I sat, his hand deep in his pockets. He didn't say anything for a while, just looked at the water. Then, after a moment, he spoke.

"Dean's a jerk," he said simply. "Yelling at you like that... breaking up in front of everybody... the guy's a total jerk."

I knew he was trying to make me feel better, but it really wasn't working. "No, he's not," I sighed. "He's perfect."

"Oh, come on, Rory," Jess sat beside me. "You don't believe that, do you?"

"He's as close to perfect as anyone can be," I insisted, not looking at him. "He is... well, I guess was... so sweet."

I could almost picture Jess rolling his eyes. "'Sweet' doesn't make him perfect."

"Look, I don't want to talk about this right now," I said, standing up. My voice broke at the end of my sentence. "I'm tired, my head hurts, my feet hurt, and I just got dumped by my boyfriend of two years. I appreciate the sentiment, but right now, I just want to be alone."

Jess rose to his feet, looking at me. "Okay," he nodded. "See you later."

We turned to walk away at the same time, going opposite directions. I half-ran, half stumbled back home, figuring that my mom was still at the school. Sure enough, as I unlocked the door, it was pitch black inside. I flipped on a light in the entryway, then the kitchen, and then my bedroom.

I changed into some jeans, a black T-shirt, and a pink shrug, before going into the bathroom to do some damage control. I brushed the tangles and curls out of my hair, then wiped off the smeared mascara. When that was done, I looked at myself in the mirror. I looked awful. My eyes were all red and swollen, there was a mysterious red splotch on my left cheek, and my lips were dry and cracked. Though my hair was mostly untangled, it still looked frizzy and untamable.

Suddenly, I lost the will to stay upright. I collapsed to the floor, laying my head next to the toilet, curling up into the fetal position. A little while later, I heard the sound of the door opening, and my mother's furious footsteps going up the stairs. She must have been pretty mad at me. After a few more seconds of silent wallowing, I sat up, ready to go back into my room and lock the door. Just then, my mom appeared in the doorway, having also changed into more casual attire. The disappointment and anger was clearly etched on her features, but a split second later, they dissipated into obvious pity.

I hated being pitied. But I was pretty damn pitiable right then. I sobbed.

Without a word, she sat on the floor beside me, and guided my head to her lap. "Just cry, babe," she whispered. "Go ahead and cry."

I didn't need telling twice.

A/N: Yes? No? Hate? Love? Don't care? Tell me!