DISCLAIMER: I do not own the Vampire Diaries (books or tv show) or the movie Never Been Kissed. I'm just a fan who wants to share some writing. ;)

Hey. This story is based off of the movie Never Been Kissed. Yes, I know Elena is OOC - very OOC in the beginning of the story, but by the end of the story she'll be the Elena we all (most of us) love. :) Also, Damon is a bit OOC too, but remember that he's also a teacher and doesn't have all the vampire-and-treated-like-shit-for-a-hundred-or-so- years angst. I'm trying my best to keep the characters in character while also playing the roles they serve in this story.

Anyway, I hope you enjoy! Oh, one last thing: I went through and edited this because incorrect grammar annoys me to no end and it's unfair for you guys to read something that doesn't make sense, haha.

Such a pretty face

It warms my soul

And your sweet blue eyes

they shine like gold

- Found You, Ross Copperman

Prologue

The excited audience only made my palms sweat more. The back of my neck itched but I stayed paralysed, holding my breath.

3:27

There's still plenty of time, I convinced myself.

2:31

The microphone in my hand shifted from one to another, creating fuzzy static to blare out the speakers.

1:21

I squeezed my eyes shut. This wasn't supposed to happen. I was supposed to enrol into high school as a 17 year old, get a story, and get out.

But of course, luck was never one my side.

0:13

I sat down at the large conference table, my hands folded neatly on the wooden surface. My hair was pulled back in a tight ponytail, not a hair out of place. I looked professional. And proud.

I was 25, the youngest copy editor at Mystic Falls News. I felt the corners of my lips starting to turn upwards, showing a smile full of pride.

"Elena!" my best friend, Caroline Forbes, sang as she sat down next to me. The meeting doesn't start for another five minutes, but Caroline and I knew that. We always come in early for meetings so we can sit beside each other and pass notes. Normally, passing notes was a big "NO!" for me, but seeing as I never get asked anything and the meeting never has anything to do with me, I thought it was perfectly fine.

Plus Caroline gets impatient if I don't read her gossip filled notes.

"Hey Care," I responded, bringing my cup of green tea up to my lips and taking a sip.

"So you'll never believe what I did last night - or, actually, who I did." A wicked gleam shined in her light blue eyes, a smug expression covering her pretty features.

"Let me guess," I said sarcastically, like I didn't know. "Tyler Lockwood."

Caroline let out a high pitch giggle. "Yes! Oh my gosh, he was absolutely fantas-"

I held up a hand. "Please, spare me the details."

Caroline pouted, playfully glaring at me. "Sorry, forgot, you've never even been kissed before."

I quickly looked around the room, making sure no one heard, before letting my eyes rest on Caroline. "Shut up!" I hissed.

But she just rolled her eyes, lifting one of her shoulders slightly, as if saying, Whoops.

"How is everyone?" came a loud voice, hushing everyone's chatter. "Never mind, don't answer. I don't care."

Kol Mikaelson was the owner of Mystic Falls News, and frankly, not the nicest. He was 47 years old, rich, and just a jerk. Although I did have to respect him quite a bit - he was well known and knew what the residents of Mystic Falls wanted to read.

He walked around the table, hands locked behind his back, completely at ease. "You know, I was at a family reunion on the weekend."

A small snicker escaped from someone, and I whipped my head around to face them. Everyone, including me, was showing the new worker pity.

"Did you just laugh while I was talking?" boomed Kol Mikaelson, his hands unlocking from behind his back and crossing over his chest.

Trevor Smith stiffened, his eyes widening. "Er, I'm sor-"

"Out!" Kol Mikaelson pointed towards the door, his face showing no justice. "You're fired."

I flinched, and so did everyone else. Trevor grabbed his things and stumbled out the door. When the door closed everyone snapped their attention back to Kol Mikaelson, and Caroline quickly stopped writing a note, knowing today was not the day to trade gossip with me.

"As I was saying before I was so rudely interrupted," said Kol, starting his pacing again. "I was at a family reunion on the weekend." He paused, as if challenging anyone to let out a snicker like Trevor had done. When silence filled the room, he continued on. "And when I was there, I discovered something."

I held my breath as he passed me, keeping my back perfectly straight.

"My grandson is allergic to peanuts!"

I made eye contact with Caroline, our expressions mirroring each other.

What the hell?

"And that's when I realized, do we actually know ours kids? Our grandchildren? They're gone 6 or 7 hours a day at school, then out right afterwards. And I thought to myself, 'What do parents who read the Mystic Falls News want to know?'" He lifted a hand up, making a, someone answer me gesture.

I slowly raised my hand. His eyes landed on me and my heart raced.

Wrong answer and I'm out the door, just like Trevor.

"What…" I gulped, wiping my wet palms on my long grey skirt. "What their kids are doing most of the day…?"

He nodded sharply, his gaze never leaving me. "Exactly. Which is why you are going to enrol into high school and find that out, Elena Gilbert."

Me. Going undercover. Reporter.

I nodded quickly, nodded too long. Caroline squeezed my knee, congratulating me.

"And I want a story. A good one. If not…" Kol smirked, his eyes amused. "If not, you are fired. Meeting over."

"I'm going undercover Jer!" I squealed into my phone. "Me! A reporter undercover!"

"What are you going undercover as?" my brother asked. I could hear him struggling over the phone and knew he was at the Mystic Grill, working.

"A high school student!"

I heard something drop and Jeremy curse. "'Lena, that's great and all…. But do you remember what high school was like? And what they called you?"

I faltered. I wasn't exactly popular in high school. Hell, I was the loser in high school. Frizzy hair, huge glasses, braces, baggy clothing. You name it.

And the name.

Insane Elaine.

It started when the most popular boy in school came up to me. His other friends were laughing, and I knew it was a prank, but the minute his blue eyes looked at me, I knew I didn't care.

His name was Matt Donovan, and I had only been planning our wedding since grade 3, when he moved into Mystic Falls.

His sloppy grin made my breath catch. He extended a hand, saying, "I'm Matt Donovan. You?"

It was grade 10. Of course I knew who he was. He knew that. But I was awestruck, lost in his beauty.

"Elena Gilbert," I breathed out.

His eyebrows scrunched in confusion, which I found completely adorable. "Sorry? Elaine Hilbert?"

I shook my head, but before I could say anything, Jeremy, my younger, popular brother came up to us. "I like to call her Insane Elaine," he said, grinning.

Obviously, he was joking, and I shoved him playfully, but before I could object, Matt was walking off, laughing and telling his friends.

Insane Elaine. That's who I was known as from then on.

"Insane Elaine," I mumbled breathlessly, my heart racing for a whole other reason now.

"I know," Jeremy said sadly. "I was the one who made it up."

I ran to my bathroom, pressed speaker on the phone, and turned on the sink, spraying cold water all over my face. "I can't do this," I whispered, staring at my reflection.

Or, actually, my grade 10 self stared back, haunting me.

"Yes, you can!" Jeremy insisted. "I just want you to remember that it won't be easy."

I nodded, though I knew he couldn't see. "Right," I said, my voice cracking. I cleared my throat, then saying louder, and in a stronger voice, "Right."

It was Monday morning, first day of school. I had woken up at 5:30, and did everything Caroline had instructed me to do.

Before I left, though, I stared down at the checklist.

Curl ends of hair to create soft look? (Check - though research on curler burns!)

Apply makeup? (Check, though with some difficulty - remind Caroline to give me another lesson.)

Wear Caroline approved clothes that she picked out? (Yes - well, sort of. Added some accessories of my own on!)

Brushed teeth? (Uh, yes. And flossed.)

Perfume? (Hope no one else chokes on the scent like I did! Strong stuff!)

Check school bag? (Not sure why I have two extra pairs of jeans, though I'll trust Caroline that I need it.)

I felt like another person as I shoved the checklist into my backpack, heading out to my car. When I slammed my car door shut, my fluffy white scarf got caught.

"Shit," I muttered, tugging on it. The sound of ripping froze me, though, and I slowly looked down at my scarf.

And loved it.

The jagged edge gave the scarf character. It made it unique.

When I arrived at the high school, Mystic Falls High, I pushed every bad memory away.

I wasn't "Elaine Insane", the biggest loser of the school.

I wasn't Elena Gilbert, youngest Copyeditor at Mystic Falls News.

No, I was Elena - er, last name? I quickly pulled out my fake ID I had my friend, Alaric Saltzman, make for me. Holt.

Elena Holt.

I like it.

I opened my car door confidently, my eyes only glancing at the small scrap of scarf that fell free from the door for a second before lifting my head high.

I readjusted my neon pink belt that I added to accessorize the outfit Caroline had picked out for me, my matching pair of sunglasses making me feel like a celebrity.

I walked to the front of the school, mistaking the odd looks I was getting for admiration.

So I smiled back.

After I got my schedule, I headed to my first class, English. Mystic Falls High was still the same from when I was younger. I wasn't great at acting, so I hoped the look of confusion covering my face looked real.

When I reached the English classroom, I saw that it was empty except for two other students sitting down. I sat down in the middle row, excitement taking over me.

I'm undercover! I'm UNDERCOVER!

In less then a minute the classroom was filled with students. I heard someone clear their throat and looked up.

The girl had dark hair, much like mine, except it was curled. Her dark brown eyes glared at me and her lip glossed mouth twisted in disgust. The girl beside her had a slender hand placed on her jutted hip, her long blonde hair twisted into some complicated up do.

"Yes?" I asked, trying to keep my voice steady. I may be 25, and they may be 17, but damn, they looked intimidating.

"You're sitting in my spot," the dark hair girl said, like it was the most obvious thing ever.

"Oh! I'm sorry, I didn't realize the seats were assigned." I stood up quickly, allowing the girl to sit down.

"They're not." She smirked up at me, showing flawless white teeth. Gulping, I looked around the room, looking for an empty spot. I darted towards the one in the front row beside a dark skinned girl.

"Just ignore them," the girl said to me with an eye roll. "They think they own this school."

"Who… who are they?"

"Katherine Pierce and Rebekah Michaels," the girl responded. "And I'm Bonnie Bennett."

I shook hands with her, grinning. "So where's the teacher? Mr… Salvatore?"

Bonnie pointed towards the man by the door. "There."

My eyebrows rose in surprise. That's a teacher? Damn.

"His full name is Damon Salvatore," Bonnie whispered to me. "He's hot, I know."

I looked back at her. "Hot? That's an understatement. Since when do teacher's look like that?"

Bonnie giggled. "True."

Damon Salvatore walked to the center of the classroom, his blue eyes scanning the room while he ran a hand through his dark hair. "It seems like we're just missing one person today," he said, causing everyone to be quiet.

Just then someone opened the door. He had light brown hair and from what I could tell from where I sat, green eyes.

And he looked nothing like my high school crush Matt Donovan, but I couldn't help but think he did look like Matt Donovan.

Sure, Matt had blonde hair with blue eyes and this guy has brown hair and green eyes, but there was something about them. They both shared the same confident, mysterious look that made girls go crazy whenever they glanced your way.

"So nice of you to join us, Stefan," Damon Salvatore said.

Stefan just grinned in reply before sitting down beside Katherine.

"That's Stefan Salvatore," Bonnie whispered to me.

"Salvatore?" I mouthed backed.

"They're cousins." After that, Bonnie turned around to face the front of the classroom.

"Elena Holt, welcome to Mystic Falls High," Damon Salvatore said, smiling. "I'm Mr. Salvatore, but just call me Damon."

I nodded, because that's the only thing I could manage to do.

Then Damon started the English lesson. I knew everything, of course. All the answers. Of course I did, I'm 25 and a writer.

Not 17.

But I had to admit, it was nice being 17 again.

I hope you guys enjoyed reading my TVD version of Never Been Kissed. It's a nice, funny movie that I definitely recommend.