Y/n was 'working' for Augustine in 1953, the time she spent there she fell inlove with a vampire, Enzo. One of her subjects.

*flashback*

Y/n walked into the hallway with her notepad and a pen, her heels clicking, her lab coat her red blood splattered on it. She looked around so make sure no one was around.

"Enzo." She smiled at him.

"Y/n?" He smiled, "hello gorgeous."

"I'm gonna help you and your friend out of here." She held onto the bars.

"It's to dangerous y/n." Enzo spoke.

"It's worth it. I want to be able to hug you. Hold you. Kiss you." She smiled.

"Just be careful." He held her hands.

"Tonight when they bring you upstairs. Be ready." She smiled.

She reached in her pocket and pulled out a blood bag, handing it to him.

"And one for your friend." She smiled walking over and seeing the blue eyed man on the floor bleeding, "What's his name?"

"Damon." Enzo spoke.

"Damon. Here." She tossed the blood bag to him.

"Thank you." Damon spoke and she smiled at him.

*later*

Y/n walked into the Event, she had a pink dress with her black heals. Her hair was curled. She walked further in and saw Enzo and Damon. Enzo's eyes lit up and she walked over.

"Father. We can use me to show them what we've discovered." Y/n spoke.

"As you wish Daughter." He spoke.

They brought Enzo out and she hadn't realized how tall he was even when she was in heals.

Her father cut Enzo's hand, then y/ns. She winced and enzo was pushed back to the other guards.

"Now drink." Her father spoke.

"How much?" She questioned.

"as much as you want." He nodded.

She drank all of it and looked at Enzo and nodded.

y/n watched her father bring the guests to the celler to show them where they hold the vampires.

She opened the door to the cell Damon and Enzo were in.

"Go run." She spoke, Enzo kissed her and smiled.

"I'll be back for you." He vamp sped away.

"Damon." She stopped him.

"Thank you y/n. I'll never be able to repay you." He smiled.

"Damon you have to kill me. To make it look like you got away yourself." She spoke.

"What? No." He argued.

"It's ok." She nodded, "do it however you want."

"I'm sorry." He grabbed her and bit her neck drinking enough blood to kill her.

"Y/n!!" He turned and saw her father, he placed her body on the floor softly.

"Goodbye y/n." He kissed her forehead.

Damon killed all the whitemore except one.

*years later*

Damon was back in Augustine with Elena.

"How'd you guys get out? What helped?" Elena questioned.

"Not so much what, more so who." Damon spoke getting flashbacks of y/ns smile and her helping him, "Y/n Whitemore, she helped us get out."

"What happened to her?" She questioned and Damon stayed silent for a minute.

"I killed her." Damon sighed, "I didn't want to but she wanted to, she wanted to die at the hands of her friend than her own father. So I did it for her after Enzo left."

*after Damon was shot*

"Welcome to Augustine." Elena turned her head and saw a girl stuck to a chair.

"What's going on?" Elena spoke.

"Wes the crazy doc is going to make you watch him torture me." She looked at he ceiling.

"How long have you been here?" Elena asked.

"Almost 70 years." She sighed.

"Wait- are you y/n Whitemore?" Elena gasped.

"How do you know me?" Y/n snapped her head toward Elena.

"Damons here. He'll help us. You remember him right?" Elena questioned.

"Damon Salvatore. I haven't heard that name in a long time." Y/n smiled to herself.

*later*

Damon and Enzo were talking.

"Enzo." Damon spoke, "how?"

"Wes let me go, told me to figure out what you want for my freedom and if you don't he's gonna kill this darling Elena girl and Some other girl in there with her." Enzo spoke.

Enzo was telling his story and Damon realized Enzo had no idea what happened to y/n.

"I spent years looking for y/n. Only to find her grave stone. She killed herself. I figured it's so use lining if I couldn't be with the girl I was in love there was no point in living." Enzo spoke.

"Y/n didn't kill herself." Damon spoke.

"What?" Enzo turned.

"After you left, she asked me to do it. She didn't want to die at the hands of her father. So I killed her. Drained her of her blood until she stopped breathing." Damon sighed.

Enzo and damon were fighting while Stefan got Elena.

She woke up on a couch.

"Did you get the other girl?" Elena coughed.

"What girl?" Damon questioned.

"You didn't know?" Elena questioned.

"Know what?" Enzo stepped forward.

"Y/ns a vampire and Wes has her." Elena spoke.

"What? No I was there she's not." Enzo yelled.

"Wes kept you two apart because he knew about your love story.

Damon and Stefan got to Wes' lab as Enzo didn't believe she was alive.

Wes was about to put the syringe in y/ns chest.

"Y/n!!" She recognized Damon's voice.

"Damon!" She yelled, she hit her head into Wes' making him fall to the floor.

Two people ran down the stairs.

Her vision became blurry, and she opened them as the ties were ripped off her.

"Damon?" She spoke weakly.

"Y/n." He smiled holding her face, "oh thank god your alive."

He helped her stand up and y/n turned to see Wes about to go after the guy with Damon.

She shoved him out of the way and bit Wes' neck, She continued drinking his blood and she fell to her knees squeezing his body to get every last bit of his blood. She felt his body go limp and his head fall off.

She stood up and looked at Damon, she had blood dripping down her face and her neck.

Stefan's eyes went black and his veins were showing.

"I gotta get out of here." Stefan vamp sped out.

"Your a ripper." Damon spoke.

"Well duh I mean when I was human I was addicted to Vampire blood I became a vampire and human blood was my Weakness. When I drink from a person I can't stop." She spoke.

"Enzo would hate to see you like this. But he has to." Damon grabbed her and snapped her neck.

*later*

Y/n woke up in a familiar class room.

"Ugh I've always hated this classroom." She sat up and felt the dry blood on her face, "gross."

"1955. Classroom massacre. 37 students dead. Bodys drained of blood. Heads torn off." Damon read, "your worse than Stefan."

"Oh come on Damon! I'm a vampire! I'm free!Let's have some fun!" She smiled.

"Fine." They walked out.

They were at a Rager and y/n had already killed atleast 10 people.

Y/n kept hearing someone say her name.

"Is it just me or is someone saying your name?" Damon spoke.

" I need some air." They got outside and y/n saw Enzo.

"Enzo?" She smiled.

"Y/n." He smiled and ran to hug her, she kissed him and held onto him.

"Enzo here's your Ripper girlfriend. Have fun." Damon spoke walking away.

Y/n and Enzo held each other in their arms not letting go.

"Why did you want Damon to kill you?" Enzo questioned.

"I know you wouldn't do it." She spoke.

"Your right. I wouldn't have been able to." He smiled.

"I have waited to be reunited with you for nearly 70 years Lorenzo St.John." She smiled and finally said the words she never thought she'd be able to.

"I love you." She spoke quickly.

"You have no idea how much I love you y/n." He kissed her not caring that he could taste the blood of her victims on her lips.

Y/n and Enzo were chaos together but they loved it. Y/n was his ripper girlfriend and Enzo was her more in control boyfriend. Let's just say at he years went on Damon and Enzo spent a lot of it trying to help y/n and Stefan's ripper problem. Though they didn't fix it they found a way to live with it.