A/N: This is just something that has been dwelling on my mind for a while. Serena and Damon just seem to be a perfect match. They both do what they want and when they want. Don't like it, don't read it. I know my work isn't perfect and somethings seems a bit superficial.

Summary: What if Serena went to Mystic Falls instead of Nightly? During 2x19 "Klaus", Serena is second cousins with Caroline, her Grandmother was a Forbes. Sheriff Forbes makes the Salvatores take her into the boarding house.

Disclaimer: I don't own anything, anything you recognize is from the CW.

I.

Serena arrived at the Salvatore's wearing the same yellow dress she had sex with Nate with. She arrived with 20 suitcases filled with her things.

Serena went to the boarding house, and rang the doorbell.

Almost only seconds latter, a dark haired man with light piercing blue eyes opened the door.

"Yes?" he asked smirking, like Chuck.

Serena rolled her eyes and pushed a lock of blonde hair back behind her ears.

"Is this the Salvatore Boarding House?" Serena asked.

Damon grinned, "Sheriff Forbes' cousin?"

Serena sighed in relief, "Yeah, I'm Serena, Serena van der Woodsen."

Damon started smirking again, "Looks like we're going to be spending a lot of time together."

Great… probably a lesser version of Chuck. Serena thought.

II.

Serena walked into The Grill wearing a short orange spaghetti strap A-line dress and a matching orange clutch. How she managed to pull it off remains the magic of Serena van der Woodsen.

Damon was sitting at the bar drinking a glass of scotch on the rocks with Alaric next to him.

"Yeah, yeah you did." Alaric said.

Scotch on the rocks? God, he really is a lesser version of Chuck.

The difference between Chuck and Damon though, was that Chuck would never wear leather. Too 70s.

"Kettle One please." Serena said placing a 100 on the table, then winking, "Keep a tab open."

The bartender smiled at her flirtingly.

Serena then noticed a cute person behind her.

"Gentlemen…" the stranger said, "Why so glum?"

"Klaus I presume." Damon said making a pained expression.

Serena then decided to butt in. "You must introduce me to your friend Damon."

"We're not friends." Damon said.

Serena pouted and looked back to Klaus while saying, "Then let me introduce myself, Serena, Serena van der Woodsen."

Klaus smiled, then attempted to compel Serena, "Make yourself useful elsewhere Serena."

Serena rolled her eyes, "Arrogant much?"

She then got a text from Gossip Girl.

Hey boys and girls. Gossip Girl here. Looks like S is still living it up in a dingy old town called Mystic Falls. Town has the highest rate of animal attacks S, remember to stay safe S, wouldn't want our favorite blonde bombshell to get mulled by a bear do we?

Xoxo

Gossip Girl

Serena then proceeded to get a text from Georgiana.

Mystic Falls, really S?

Damon lifted his eyebrow and looked perturbed by the fact Serena hadn't left yet.

Serena wasn't on vervain.

III.

The blood of a Sinner turned Saint, that's what cured a werewolf bite.

Serena turned out to be a saint that sinned.

What distinguished her from normal good girls gone bad or bad girl turned good was the fact she was unable to be compelled even when she wasn't on vervain.

IV.

They didn't know how they did it. After the sacrifice and everything going haywire, Klaus was alive granted that. The hybrid curse was broken also granted to Klaus.

When Klaus came back, he came for Serena because, apparently Serena had captured his interest. Apparently he took her virginity. (Serena was too drunk and high on drugs to remember.)

Most surprisingly, it was Elijah who saved her from his brother's grasp.

V.

They didn't know how they fell in love, they just did. They were just there for each other.

They partied together; they got drunk together, not really surprisingly though they slept together.=-[

VI.

It's surprising really, Serena mused one night they were laying in bed.

All of the ingredients Klaus needed to break the curse gathered from Mystic Falls.

The Doppelganger, a Werewolf, a Vampire, and a Witch. Not only that, all the ingredients were friends and grew up with each other.

Somehow the circle seemed to also reflect the NJBC (Nate, Chuck, Blair and her).

The Wild Child: Serena/Damon

The Jock: Nate/Tyler

The Princess: Blair/Elena

The Basket Case: Dan/Caroline

The loner/rebel: Chuck/Jeremy

VII.

One day, he just finds her packing.

"Where are you going off to?" Damon asked.

Serena looks at him, and it is then that he notices that she's crying.

"What's wrong?" He asked sounding and looking worried.

Serena just shakes her head, still crying, and brings her things downstairs on her own and leaves him.

VIII.

Damon had come to the Upper East Side in search of Serena because apparently Serena had gone in a downward spiral and nobody could find her yet.

"If anyone could find her, it's you." Caroline said on the phone.

Serena turned out to be partying it up with a red head in an underground bar in Brooklyn of all places.

The thing is that she didn't look wasted.

When he saw her, she was sitting on a bar stool with the red head surrounded by tons of guys, but she wasn't paying attention to any of them, she's been looking at him since he walked in.

Damon made his way through the crowd to her.

"Serena, why haven't you come home in days?" he asked.

Serena blushed and looked away saying, "That's not any of your business Damon."

"It is my business when you make everyone around me worry about your safety."

"Svetlana." The red head slurred. "Why don't we take your friend here to that hotel across the street and have our way with him?"

"We can't Savannah, he's too much of a party pooper." Serena said getting bubbly again.

"Party pooper or not, he has one hot bod." The read head said checking him out.

"Yeah." Serena whispered almost inaudible.

"Look," Damon said, "I'm not asking much but just go home for a night once every two days at least, stop making people worry about you."

Damon then disappeared.

IX.

"What are you doing here?" He asks, shocked that she dared show her face back in Mystic Falls.

"I wanted to clear the air with you." She says.

Damon sighs and slumps his head, "Let me guess… you can explain."

Damon then looks her back straight in the eye and says, "I don't want to listen to it."

Serena shakes her head, "No, let me explain."

Serena then takes Damon's hands and says, "My brother attempted to commit suicide."

Damon looked loss for words, a first.

X.

Serena smiled as she walked down the aisle a week latter carrying an arrangement of flowers. She's in yellow, but it's not their wedding. It was the wedding of Lily van der Woodsen and Bart Bass.

Damon smiles watching her go down from a seat close to the front.

He's sitting next to her friend, Blair, they don't exactly get along, but she thinks he's at least a step up from Brooklyn.

Apparently Blair thinks that he's keeping Serena away from them, which he is.

XI.

When they get into their first real argument, furniture fly.

"You used people like puppets. PUPPETS!" She screamed, "You don't feel anything! You're a monster, impossible to love."

"Fine if that's what you think, let's break up." Damon said throwing his glass in the fireplace.

"Fine." Serena says turning her heels and walking away, back to her bedroom.

They break up for the first time officially and avoid each other.

XII.

They don't see each other again until Elena and Stefan's wedding the next week.

Serena was sitting front row watching Damon stand next to Stefan as Stefan gave his vows.

She's about to leave after the reception, but Damon stops her.

"Wait." He says.

She does, and they stare at each other for a long time.

"I've missed you." He says.

Serena feels as if she were about to cry, "I've missed you too."

They hug.

"Let's start over, it won't be perfect, but that's the beauty of eternity. We have all the time we need." Damon says hugging her.

She says yes.

XIII.

Two years latter, Serena is walking down the aisle wearing a white dress like Grace Kelly's and Kate Middleton's.

Blair is her maid of honor, while Caroline, Elena and Bonnie are her bridesmaids. Stefan is his best man and surprisingly, Elijah, and Jeremy are his groomsmen.

XIV.

Six months latter, she's turned into a vampire. They promise to accept eternity with each other.

Serena had a long history of leaving, going, coming, and breaking hearts without even knowing or trying. But with Damon, everything is different, they understand each other. It doesn't matter if they have a fling with someone else, as long as it is them that they choose in the end. So they try and succeed in not completely screwing things up (again).

Serena is just the girl that wants to be loved and Damon is just the boy who wants to be chosen first and above all.

Serena Cecil Van der Woodsen always chooses love first and so has Damon Salvatore, it's been about time, they choose each other.

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