Emily leaned against the many gray lockers that littered the crowded hallways of Mystic Falls High School with her twin sister and best friend. Stefan spoke up to the two girls, "Damon hasn't said a word to me. Every time I try to talk to him, he shuts me down," Stefan explained.

"Do you think he's still trying to find Katherine?" Emily questioned Stefan. She hoped Damon would give up on Katherine so she wouldn't come to Mystic Falls and burn the small city to the ground with her destruction.

Stefan glanced over at Emily, "I don't know." Stefan paused before explaining, "he waited 145 years only to find out that Katherine could not care less. I mean, it's gotta hurt, right?"

Emily shrugged her shoulders before smirking, "and it couldn't have happened to a nicer guy." Emily glanced over at Elena when she heard her chuckle. She smiled over at her younger sister before giving Elena a high-five.

Stefan chuckled at the two sisters before looking at his girlfriend, "you have every right to be upset with him." Stefan glanced over at Emily before asking, "have you guys thought about what you are going to do?"

"About what?" Elena questioned before continuing, "Isobel, our vampire birth mother, who's related to our vampire ancestor Katherine, who screwed over your vampire brother?" Elena shrugged, "nah, I haven't thought about it at all."

Emily smirked, "Damn, Elena. I'm loving the attitude," Emily joked while looking over at her sister.

Stefan chuckled, "I'm sorry I brought it up."

Elena sighed, "it'd just be nice if we could get through one day without having to deal with any of it. No vampire mother or brother."

"Amen," Emily praised her sister. She couldn't remember the last time she had a vampire and drama free day.

Stefan rose an eyebrow at the two girls, "no vampires at all?"

Emily sighed loud and dramatically, "I guess you can stay, if you must," Emily joked.

Stefan smiled at the older Gilbert while Elena rolled her eyes at her sister before answering her boyfriend. "No vampires but you. I just want to get us back to normal stuff like school and homework and," Elena gasped, "here's a thought, fun."

"Ooh," Stefan smiled, "that sounds good to me. When do we start?" The two girls chuckled before following Stefan down the busy hallway.


The two girls were standing by Stefan's locker while he was placing books inside, when suddenly a happy Caroline popped up next to the two sisters. Emily chuckled lowly when Elena jumped in fright when the blonde showed up. Emily was used to Caroline popping out of nowhere since she was her best friend.

"I'm thinking nothing huge, just a dinner at the Grill, maybe a late movie," Caroline exclaimed as soon as she close enough for the trio to hear her.

"You mean like a double date?" Stefan spoke up while he was looking through his book bag.

Caroline shrugged, "two pair out on a Friday night, couple. Yeah. a double date," Caroline smiled at Stefan and Elena.

"Do you think that's a good idea?" Elena asked quietly.

Emily smirked over at her sister, "it could be fun."

Caroline smiled brightly at Emily before turning back to Elena, "yeah, listen to your sister. We all haven't gone out together before and I don't want it to be uncomfortable for us." Caroline paused before continuing, "look, the couple dynamics have changed and there's been a little awkwardness between you, Matt, and me and I just think it's important that we get over it."

Elena shook her head, "I don't know."

"I think that sounds like a great idea," Stefan spoke up from behind Elena.

"You do?" Elena questioned her boyfriend in shock.

Stefan nodded his head, "yeah. A nice evening out with friends. Sounds fun," Stefan whispered, "as in 'fun.'"

Emily chuckled at Elena awkward expression and the smiling Caroline. "A double date it is," Elena smiled over at Caroline.

"Okay!" Caroline smiled before her smile dropped and turned towards her best friend, "oh! Emily do you want to join us?"

Emily shook her head and chuckled, "oh, no, no. I don't want to be the fifth wheel. I have a date with my couch and some yummy chocolate ice cream." Emily smiled at the blonde, "you guys have fun."

Caroline smiled at her best friend before turning to the couple, "so, we will see you tonight," before strutting down the hallways of Mystic Falls High School.

Emily glanced over at her sister, who was raising one of her eyebrows at Emily. She rolled her eyes, "what? I'm having a vampire free day too."

Elena shook her head and chuckled at her twin sister, after a moment, Stefan also joined in the laughter. Emily rolled her eyes at the two and made her way through the hallways and towards class with the couple following behind while still laughing at the older Gilbert.


After Elena had left with Stefan and the house was quiet, Emily made her way towards the kitchen in her black sweatpants with a red sweater. She opened the freezer, and smiled when she saw her chocolate ice cream. Emily grabbed the ice cream and spoon from the drawer before making her way to the living room.

Emily sat down in the middle of couch and picked up the remote control and began to flick through the many channels, trying to find a good movie. Before Emily could find a movie, someone spoke up from behind her, "what are you doing?" the voice spoke with humor.

Emily glanced over her shoulder and saw that it was her aunt Jenna. Emily pointed towards her chocolate ice cream, "having a date with this yummy goodness."

Jenna rolled her eyes, "why aren't you out having fun on a Friday night?"

"Elena's having a double date with Stefan, Matt, and Caroline," Emily explained.

Jenna grabbed the ice cream from Emily's hand and before she could complain, Jenna quickly spoke, "nope. You aren't staying here on a Friday night. We're going out to the Grill and we are going to have fun."

Emily sighed, "fine," and she stood up and walked towards the door to slip on some shoes.

Jenna rolled her eyes, "no, no. we are going to do this the right way." Jenna smirked before grabbing her niece's hand and pulled her upstairs towards Emily's room.

Emily looked at her aunt in confusion when Jenna ran towards her closet and began to look through her clothes. "What are you doing?" Emily questioned Jenna.

Jenna stopped her movement, glanced over at her niece, and smiled, "I'm dressing you up," Jenna stated like it was obvious.

Emily rolled her eyes, but decided to let Jenna continue looking for an outfit. She didn't mind having Jenna dressing her up. Emily used to always dress in Jenna clothes when she first got interested in fashion.

"This is the one!" Jenna yelped in happiness before pulling out a dress and pushing it right into Emily's arms. She didn't have time to look at the dress before Jenna was pushing her across the room and towards the bathroom, "go put it on," Jenna commanded before closing the door.

Emily shook her head and quickly slipped on the dress. She looked into the mirror to see what dress Jenna gave her and saw that it was an off the shoulder black and floral dress. Emily shrugged, she was happy with the dress. It was really cute. Emily knew that she and Jenna always had the same style.

Emily walked back to her room just in time to see Jenna sat down black open-toed heels, a pair of earrings, a rose gold ring, and a black purse on her bed. Emily chuckled and spoke, "you're really going all out, aren't you?"

Jenna looked up her niece with a smile, "you look amazing. And yes I'm going all out, we're going to have a blast tonight! Now hurry up! I'll be downstairs."

Emily chuckled before slipping on the black heels and carefully placing her earrings and ring on. She glanced into her mirror to make sure her outfit was perfect before grabbing her bag from her bed and making her way down stairs.


Emily and Jenna quickly made their way into the crowded Mystic Grill when Jenna saw someone that she didn't think would come back to the small town. "Kelly? Kelly Donovan?" Jenna called out. Emily looked to where her aunt was looking, and sure enough, Kelly Donovan was at the bar with none other than Damon Salvatore. Emily groaned quietly, there goes her one day of no vampires. But Emily decided to humor Jenna for the night. Jenna deserved to have night off of having to take care of three teenagers.

Kelly turned around to see who called her name and smiled when she saw the strawberry blonde. She quickly jumped off the bar stole before pulling the women in a hug and exclaimed happily, "Jen!"

Once Jenna pulled away from the hug, she commented with a bright smile, "I heard you were back in town." Jenna looked over to the man that was sitting next to Kelly, who happened to be Damon, "she used to babysit me."

"And then, I used to party with her," Kelly also told Damon with a smile.

Emily leaned against the bar and smirked, "ooh, Jenna used to a party girl, do tell."

Jenna chuckled and pointed towards Kelly, "this woman is crazy."

"Not as crazy as you," Kelly smirked at Jenna before winking over at Emily.

Jenna shook her head, "I'm not anymore."

"Well sit," Kelly commanded, "drink!"

Jenna shook her head once again and wrapped an arm over Emily's shoulder, "I shouldn't. I'm more responsible now. Haven't you heard?"

Kelly sat back on her stool and spoke, "well, take a night off, it's good for the soul."

Emily nodded and looked over at her aunt, "yeah, come on, Jenna." Emily smirked, "you said we're going to have fun."

Jenna stared at her niece for a moment before finally agreeing, "fine, fine." Jenna pointed at Emily, "but you are not drinking."

Emily groaned, "aw, you're no fun, Jenna," she scowled her aunt.

Jenna shrugged lightly before sitting on the bar stool next to Kelly and grabbed one of the shots that the bartender poured. Jenna bumped her glass with Kelly and Damon's glass before mumbling, "this is not going to end well."

Damon smirked, "can't wait," before the three adults shot back the hard liquor that was in the shot glass.


Emily watched in humor while the three adults continued to shoot back multiple shots of amber liquor. She noticed that Jenna was starting to get a little tipsy, Emily decided to take advantage of that. "Hey, Jenna," Emily called out and waited for Jenna's glassy eyes to focus on her before continuing, "do think I could have some?" Emily asked sweetly.

Jenna smiled at her niece and threw her arm over Emily's shoulder, "I don't see why not," Jenna exclaimed before pushing a small glass towards her oldest niece. Jenna then turned towards the man with the baby blue eyes and commanded, "don't be grumpy. It can't be that bad."

Damon's blue eyes focused on the glass in his hand and mumbled, "you'd be surprised. My primary reason for existence has abandoned me and after today's events the remains of the shaky ground that I walk on are about to go kaboom." Damon paused before turning his mood around and smirking over at Kelly, "let's get hammered."

"Let's," Kelly smirked before the three adults bumped their glasses together. But before they took a sip, Jenna drunkenly turned to her niece with wide eyes, "well, get in here! You're drinking with us now!"

Emily met Damon's blue eyes that was smirking at her. Emily shrugged, brought her glass up and bumped the three glasses that were raised before all four of them downed the rough alcohol.

But Jenna suddenly tucked her head down and whispered as quietly as she could, "quick,hide. We're not here."

Kelly lowered her head next to Jenna's before whispering, "why? Where'd we go?"

"Children under our care. Five o'clock. That is not good," Jenna quickly whispered while shaking her head.

Emily rolled her eyes before turning around, she quickly spotted Elena and Caroline standing while Matt and Stefan were seated at a booth. Emily shrugged, she didn't realize that they had been here the whole time. Emily turned back to her aunt and whisper, "do you know I'm one of those children that you take care of?"

Jenna padded Emily's head drunkenly, "but you are fun. So you don't count."

Emily smiled at her aunt, "thank you… I think," Emily mumbled. Jenna chuckled at her niece before pushing another glass towards Emily and pouring the three more glasses for the other two people and herself. Damon smirked over at the green eyed girl before the four downed another shot.


Emily had lost count of how many shots that she had, but she knew for one thing, that she was having a blast with her aunt, her friend's mother, and the vampire that killed her birth mother. The alcohol was blocking out her anger towards the older Salvatore, she just wanted to have fun and relax.

Emily and Jenna bumped two glasses together before downing another shot of alcohol. They both turned to Kelly and Damon when they went quiet and saw that they were extremely close together.

"So, the thing about cherries, you have to…" Damon began whispering towards Kelly.

But before Damon could continue, Kelly placed her finger towards Damon's lips and pulled out a cherry stem that was tied in a knot.

Damon smiled at Kelly and mumbled, "oh my goodness," before placing his pink lips onto Kelly and taking the cherry stem from her mouth. "That's amazing, you were fast," Damon praised Kelly.

Emily glanced over at Jenna, who's eyes were wide in shock. Emily chuckled lowly and spoke up, "that would be our queue."

"You're giving up already?" Kelly asked while continuing to stare into Damon's blue eyes.

"I need to put this one to bed," Jenna spoke with a slur.

Emily rolled her eyes at her aunt, "I think you got that backwards drunky," Emily chuckled at her aunt before grabbing her purse from the bar and looping her arms with Jenna's and guided her out of Mystic Grill.

"See you guys!" Jenna yelled out to the couple at the bar.

Emily walked down the stairs of the entrance of the Grill and waited carelessly for Jenna. Emily chuckled when she saw Jenna trip on the last step, causing Jenna to break one of her heels. "Ouch! Damn it!" Jenna yelped.

"Need some help?" A strong voice spoke up, causing Emily to jump to look up to see a man in front of them.

"Stupid shoe," Jenna mumbled while chuckling at herself.

"Lift up your other foot," the man commanded with a smile. Jenna listened to the man who broke the other heel so Jenna could walk. The man stood up and handed Jenna her broken heel, "here you go."

"Thanks, I think," Jenna chuckled at the man.

The man glanced at the strawberry blonde and the brunette that was watching the two, "was that Damon Salvatore you were with?"

Emily wasn't drunk, but she was a little tipsy so she answered the strange man with a smirk, "the one and only." Emily rose an eyebrow, "you know him?"

"We go way back," the man nodded. "He still live out by Miller Lane?"

Emily shook her head in confusion, "he lives in the old Salvatore boarding house by Wickery Bridge," Emily corrected the man.

"He's still inside if you want to go say hi," Jenna jumped up.

The man shook his head while looking into Jenna eyes, "I prefer to stay here and talk to you."

Emily smirked when Jenna froze in her spot. "Oh, nice," Jenna mumbled quietly with a smile. "Very smooth with the shoe and the flirt." Jenna paused while glancing over at the smirking Emily, "but, I'm a little drunk and a guy plus drunk me equals very bad things."

The man moved closer to Jenna and stared into Jenna's eyes, "I'm pretty sure you'd like it."

Jenna stared at the man, which caused Emily to begin to get a little nervous but she calmed down once Jenna busted out laughing. "Sorry. That was a seriously lame pick up," Jenna apologized.

Even with not a steady mind, Emily didn't like how the man was staring at Jenna, so she quickly walked over to Jenna and linked her arms with her aunt. "We should be going," Emily spoke towards the man before dragging her laughing aunt away from the strange man.


It took Emily double the time it would usually take to walk home from the Grill with the giggling Jenna hanging off her arms. Emily slowly opened the door and pulled Jenna through the entrance, who yelled loudly, "Jeremy!"

Jeremy quickly ran towards the stairs from the kitchen. "Jenna!" Jeremy looked at his sister confused, "hey, what's up?"

"Regret," Jenna mumbled onto Emily's shoulder.

Emily chuckled and told her brother, "she's drunk. I'm going to get her bed. Good night, love you Jer."

Jeremy rolled his eyes playfully before telling his sister, "good night and love you too."

Emily gave Jeremy one last smile before holding onto Jenna's arm and carefully walked her up the stairs. Jenna groaned once they made it up the stairs before leaning against Emily's shoulder. Emily chuckled at her aunt but spoke softly, "we're almost there."

Emily walked as slowly as she could, so Jenna wouldn't trip over her broken heels. Emily carefully helped Jenna lay on her bed before pulling her broken heels off and tossing them in the corner of her room. She pulled the covers up to Jenna's waist, Emily was about to walk out of the room but Jenna called out to her.

"Emmie," Jenna mumbled.

Emily sat down on the edge Jenna's bed and questioned quietly, "yeah, Jenna?"

"Thank you for hanging out with me tonight," Jenna mumbled out sleepily. "You make a fun drinking partner." Jenna chuckled softly, "but you aren't aloud to drink anymore."

Emily smirked, "whatever you say, Jenna."

Emily was about to stand up when Jenna mumbled quietly, "I miss my sister."

Emily's face saddened at Jenna's comment. Emily sat back down on the edge Jenna's bed and grabbed her hand, "you do a great job at raising us. Mom would be proud of the adult you have become." Emily gave Jenna a smile, "you deserved to have fun today." Emily bent over Jenna and gave her head a kiss, "get some sleep, Jenna. You're going to have a huge headache in the morning."

Emily quietly closed Jenna's bedroom door after shutting off her lights. She made her way towards her bedroom and quickly put on some sweatpants and a t-shirt before slumping into her bed. Besides having to hang out with Damon for the night, Emily decided the day was a success from all the drama and vampires. She was glad that she listened to Jenna and went out tonight. Emily never really had the chance to hang out with her aunt in a while, so it was fun to act carefree with Jenna. Hopefully Jenna won't remember anything that happened tonight, so Emily wouldn't get in trouble for drinking, even though Jenna was the one to give her the alcohol. Emily closed her eyes with a happy sigh, tonight was one of the fun nights she has had in a long time.