The first semester of college was nearing its end. It was the week before Winter Break, and most of the students on campus had decided to depart early. Despite the sparseness in his classroom, Damon still managed to conclude his last lecture to the class. "I'm deeply saddened that this is our last day together. While though finals are around the corner, I'm glad I've gotten to know all of you this semester. Good luck on your finals, and enjoy your Winter Break." Everyone had gathered their stuff and left the classroom. As usual, Elena was one of the last to leave. She heard her name called out by Damon. She turned towards his direction to hear what he had to say. "Do you have any plans for the break?"

"I'm going home to Mystic Falls to see my family."

Damon nods, "Have a safe trip. I mean, I know there's finals."

"Thanks. I will." she smiled. "Is there—" Damon didn't realize what he was doing until it happened. He had found himself approaching her and press his lips to hers. He had been wanting to kiss her for some time and was unsure of the right moment to do so. He reached up and caressed her soft skin before pulling away. Elena gazed up at him and asked, "What was that for?"

"Just making sure you'd come back to me." Damon's eyes gazed into hers while softly smiling down at her. Elena smiled softly, promising that she will try to go back to New York before break ends.

Damon had retreated back into the Salvatore boarding house after Elena had driven away. "What do you have to talk with her about?" asked Stefan. His arms were crossed over his chest. The door had been left slightly ajar, allowing for him to overhear the exchange of words between his brother and ex. "You heard that?" Damon sighed. "I should've told you about Elena years ago. I didn't know you two had history."

"She doesn't love me anymore."

"Then you should've seen the way she looked at me that day." Stefan was confused by this statement. What more was there about Damon's secret relationship with Elena? Despite knowing that they have met in New York, there was something about the tone in Damon's voice that alluded to something else. Stefan questioned his brother about what 'day' he meant. "The day of her graduation." replied Damon.

Elena had received a text from Caroline to meet she, Matt, Bonnie, and Jeremy at Mystic Grill. It seemed like ages since Elena had seen her brother. The two of them have always been close, despite the news of being adopted. Elena still has yet to get in contact with her birth parents. For the time being, she wasn't exactly interested in wanting to get to know them. Though she knew that she had to muster up some courage to eventually meet them face to face. The right time wasn't now. Caroline was impatient of Elena's late arrival. Elena walked through the entrance of Mystic Grill. "Hey guys. Sorry, I'm late." She sat down at the table with her friends.

"About time." said Caroline.

"I was held up." Elena briefly stated, exchanging quick glances with Bonnie. Matt inquired about where she was by asking if she was at the Salvatore boarding house with Stefan. Caroline had asked if she was getting back together with him. "You know as well as I do why it didn't work out between him and I."

"Because you moved to NYU." stated Bonnie.

"Why did you want us to meet you here Caroline?" Jeremy, out of the group, did not want to be included in hearing about Caroline's big news. Bonnie hypothesized by asking Caroline if she was pregnant. Caroline didn't take Bonnie's sarcasm very well. "I'm not a slut." replied Caroline.

"You said that in high school." teased Matt.

"Shut up. That's not the big news." She spat.

"What's the big news?" Elena wanted to get down to the bottom of this. She was sure that Damon was expecting a call from her later today about where to meet tonight. Caroline showed off her engagement ring by holding out her left hand towards her friends and announced that she was engaged. Elena and Bonnie squealed, congratulating their friend on the engagement. The three girls had stood up and hugged each other. Matt and Jeremy both rolled their eyes after muttering a quick congratulatory greeting to Caroline about the news. Elena was asked to be the Maid of Honor with Bonnie as the bridesmaid. "Who's the lucky guy?" asked Matt.

There was a minute of silence before Caroline had replied. "Damon Salvatore."

Her first Winter Break back in Mystic Falls. It was such a relief for Elena to see her family again. She arrived in front of the house, smiling upon her arrival. She paid the cab driver and brought with her the suitcase up to the front door. "Jenna, I'm home!" she called out. Her voice echoed throughout the house after entering. She closed the door behind her, only want to take a warm and relaxing bath before settling into her own bed.

"We're in the kitchen!" Jenna called out. Elena wondered where Jeremy had been since she had thought about seeing him upon her return back into town. She figured he must be out with his friends. There hasn't been recent updates about him and Bonnie. Elena kept her suitcase near the foot of the stairs and headed into the kitchen. We? She furrowed her eyebrows in confusion. What exactly did she mean? Elena entered the kitchen when she locked eyes with—"This is Damon, a friend of Alaric's back during the college days." Damon reached his hand out towards my direction.

"Nice to meet you." Elena reached out to shake her hand, repeating similar words back to him. Damon hadn't mentioned knowing Alaric to her, and so, this was the first time she had heard of this news. Jenna asked Elena about her first semester at college. Elena didn't feel like going into too much detail. "Make some new friends?" Jenna turned her attention towards her. Guess she did, in a sense. Elena thought while quickly exchanging glances with Damon before mentioning she needed to head upstairs to shower. She asked Jenna about the Christmas party. Jenna said it will be held at the Lockwood Mansion. Elena was relieved. At least she would be able to see her friends before heading back to New York as soon as the break ends. She exited the room and headed upstairs.

The Lockwood Mansion hadn't changed since the last time the Gilberts have visited. Elena remembered her last visit, which was their high school graduation party. It was Christmas Eve. Jenna, Jeremy, Damon, and Elena arrived together. Jenna had obviously brought food (meatloaf) to contribute to the already growing buffet table. Carol, Mayor Richard Lockwood's wife, had graciously answered the door. Though, it seemed like she had seen Damon before. "Damon, what a nice surprise." Her eyes sent a different message than the painted smile.

"Maybe I shouldn't have shown up unannounced." Damon let out a light chuckle.

"You're always welcome. This town is your home." Carol stepped aside, allowing for the four of them to enter the house. Jenna was led away by Carol to set down the tray of meatloaf. Jeremy said he'd go and find Bonnie. Damon and Elena were left alone. "How did you know Alaric?" Elena turned and faced him.

"Let's not talk about this here. You should go and find your friends." Damon suggested before parting ways with her. Since then, they hadn't crossed paths until Elena had gone outside to sit down on one of the patio chairs.

"May I sit?" Damon motioned towards the empty chair to my left. Elena nodded as he took his seat. Seeing him dressed the way he is, it was different than how he was typically dressed at the college. Elena had always thought of him as attractive, regardless of how he had chosen to dress. "I was at his funeral. I've known Alaric when he and… Isobel were in college."

"I wasn't aware you guys were close." Damon had begun to explain to Elena that he met Alaric through Isobel. He and Alaric were constantly going out for drinks, firstly as acquaintances until quickly becoming friends. Then a couple of years later, Alaric moved to Mystic Falls. Elena remembered when he moved here. It was during Elena's Junior year at Mystic Falls High School. Alaric hadn't discussed with her about his past, especially the details on Isobel. "Jenna must've gotten my contact number and sent me an invitation to attend the funeral. Isobel was there." said he.

"Isobel attended the funeral?"

"Your mom didn't want to meet you just yet. She said that there will be a time for you two to meet. However, not right now." Elena nodded, listening to him. As much as she wanted to say otherwise, Elena and Isobel meeting when the time is right would be the best option. She smiled softly before leaning in and pressing a light kiss on his lips.