"When was the last time we did this?" Stefan and Elena were seated at a table in Mystic Grill. The two of them were immersed in conversation while waiting for their orders to arrive. After four years since their breakup, it seems as though nothing had changed between the two of them. Elena had always admired Stefan's personality. He has always been genuine and a first love I'd never forget. "What? Date?" asked Stefan.

Elena shook her head, smiling softly. "No, since it was just the two of us. I mean, I would come to Mystic Falls during breaks. Yet, we'd never make any plans."

"We broke up Elena."

"I'm serious Stefan. We've known each other a long time. We dated in high school, sure. Did it ever occur to you that we would ever try again? I hardly ever saw you during my visits from college. I wasn't sure whether or not you've been avoiding me."

"I saw you when you came back after your first year from college. You were catching up with Bonnie and Caroline about college. It was over the summer. Caroline had just texted to meet her at the Grill. You guys didn't see me. Though, you looked genuinely happy. I wasn't sure if you'd want to see me then." Stefan admitted. "Besides, I'm sure Caroline must've mentioned that she and I were in a few classes at Whitmore college. Though, nothing had ever happened between—"

"You don't have to explain yourself to me Stefan." Elena interrupted. "I think you're realizing that you could be in love with Caroline. You two have gotten close over the years, especially since I was away at college. You two bonded, and I don't think that this date was actually intended for the two of us. I think you should go and talk to Caroline about how you feel about her." Stefan knew Elena was right. He couldn't argue with her. He stayed until their food arrived before parting ways. Elena had suggested that she would stay a while longer. Stefan had been her ride to Mystic Grill. She remembered the summer she came back from her first year of college. It was a few days after her small reunion with her friends when arrived with her suitcase at the apartment.

Elena had been staying for a few days at Jenna's house, only because she wanted to spend time with her family before actually going home to her apartment. She was more than grateful for Caroline. The two of them could finally be roommates. Well, that and Caroline had an extra guest bedroom. At the apartment, Caroline and Stefan were in Caroline's bedroom when a knock sounded at the door. Stefan pulls away from the kiss with furrowed eyebrows. "Were you expecting anyone?" Caroline shook her head. She knew that Bonnie was with Jeremy and Matt was working. It couldn't be her mom popping in for a visit either. She would be the one seeing her mom for a surprise visit. Stefan said she shouldn't keep the visitor waiting. Caroline nodded and emerged from her bedroom to answer the door. Stefan had only shortly followed after hearing the main door open. "You're home!" Caroline hugged her friend. "Wait, I thought you were staying at Jenna's." She quickly receded from the hug.

"This place is my home now." Elena smiled. The smile quickly faded when she saw Stefan. "Why is Stefan here?"

Before Caroline could answer, Stefan had reached over to grab a DVD from the shelf. "I came over to take the DVD Caroline borrowed."

"Which is?" Elena raised an eyebrow.

"The Shining."

"That's mine, and it's the one she borrowed in high school. Only recently did she give it back."

"And well, since this is our apartment, Stefan can return it here to us once its finished. Thanks for coming hon—Stefan." Caroline cleared her throat. "Stefan."

"See you Care—Caroline." Stefan takes the DVD and heads out the door, shutting it on the way out. Elena crossed her arms over her chest, asking Caroline if something was going on between she and Stefan. Caroline, though hesitated to answer, had stated that she and Stefan are friends. Elena wasn't sure whether to believe the statement or not. Caroline continued to insist that she wouldn't lie. Yet, Elena was still determined to find out the truth.

Once Stefan left, Elena had taken out her phone to make a call. "Damon, can you come and pick me up?" When Damon arrived, he had driven her over to the Salvatore boarding house. Stefan's car wasn't parked in the driveway. Elena assumed that he had gone over to her apartment to see Caroline. She followed Damon into the house when he offered her something to drink, specifically Bourbon. Elena had shaken her head before sitting down on the couch. Damon knew that this meant something serious and asked about what happened. Elena had told him about her dinner with Stefan and the reason why he could be at her place. "At least he was polite enough to stay for dinner. Wait, why would you go out to dinner with Stefan if you eventually told him that he should try and give Caroline a chance? After I had broken my engagement with her?" Maybe Elena needed that drink after all. She didn't exactly know where to begin or how to begin.

"I thought that maybe I'd give the two of us another chance. Then I realized that it wasn't going to work out. Why didn't you proceed on with the wedding? Why did you call it off?"

"You were there at the apartment. You knew I couldn't marry someone I barely knew or saw. It was during Winter break during your first year of college. I had arrived in Mystic Falls to see my brother. Stefan introduced me to Caroline. He was on break as well from Whitmore. Though after that initial meeting and constant text messaging, I couldn't make an effort to see her as much as I wanted because I was dating you. I had proposed to her with your image in my mind because to me, you never left New York."

"The break up was my fault."

"No, Elena. It's not your fault for deciding to go your own way. It's not your fault for deciding the best course of action at the time. The break up had to happen because I think for the two of us to grow as individuals, we had to be away from each other. Though, if we had tried to work it out, there could've been the possibility of us still being together. I fell in love with you, and I don't just mean for physical looks. While physicality counts for something, it's your personality that made me fall in love with a beautiful and strong woman." Damon smiled softly. Elena hadn't felt this reassured about her decision of possibly being with Damon. She had always pictured a future with him and no one else. "I can't stay here in Mystic Falls any longer. Even though it's my home, I've decided to leave for New York tomorrow morning."

"Tomorrow?"

"No."

"Elena, New York is my new home. It's always been since—"

"Take me with you."

"Your heart is here Elena, not in New York. Your family and friends are here. Matt seems to still be infatuated with you, which is something you need to work out with him. Mystic Falls has always been your home. If you come with me, you're leaving everyone behind."

"You just can't leave Damon. You used to live here. You knew my parents, my real parents. You knew Alaric long before I had gotten the chance to know him."

Damon couldn't believe how stubborn she was being, and yet, he understood. "Mystic Falls isn't going to be okay with me back in town. Many of the locals here know me too well, and the reason why I left is because they are the same people who knew my past. I've brought nothing but pain into your life Elena."

"I don't want to be with Matt or anyone else. Damon, you can't give up on me, on the possibility of us. I don't care about what you did your past or the people who can hold it against you. You have grown up into a man that I admire, that I saw a future with. I fell in love with you and am still in love with you. Though, it sounds like you've given up on me. We are supposed to fight for each other. We are supposed to work out our problems, not create problems. You moving to New York is a problem. While Mystic Falls has been a place that I grew up in and have family, as well as friends, my heart is where you are. So I don't know what you're fighting for because it seems like you are only fighting for yourself. And I hope that the two of you are very happy." Elena stood up and stormed out the Boarding house.

Elena was just packing up her belongings for her move to Mystic Falls. She was just on the phone with Jenna. She heard a knock at the bedroom door. "Jenna, I'll have to call you back." Damon opens the door when she hung up the phone. "What do you want Damon?" It had only been a day since the break up. She had booked her flight back for Richmond and had yet to think of who would be available to pick her up from the airport. Damon's hands were casually placed in his pockets. From the tone in her voice, he knew that he should've waited to tell her, except the consequences of waiting would result in him not seeing her again. "I know you're leaving in a week, and so, I decided to give you your graduation present now." He pulled a box out of his pocket and handed it to her. "This is for you. Just… don't open it yet. Open it as soon as you get home."

Elena sat at her desk, staring at the computer. After an eventful few weeks since her arrival back home, she couldn't exactly focus on work. During her lunch break, she made a call. "Matt, it's Elena. Meet me in the Town Square after work." Meanwhile, Stefan had driven the long 3-hour drive out to Richmond to drop off his brother at the airport. He couldn't believe that Damon was leaving, again. Though, what was unusual was the reason for his brother's leave. "It's better for us this way." said Damon. The two of them were having a conversation about what had happened between Damon and Elena. Stefan had to agree with Elena about his brother's actions. Stefan didn't like where things were heading. He was only looking out for Elena. "Elena needs you." Stefan was stopped in the parking garage of the airport. He helped his brother with the suitcases and headed inside. Damon had just checked in for his flight; and both were waiting just outside of the terminal before Damon passed security. "She's right about me Stef. I haven't been honest with her."

"You can't just leave. She already lost you once."

"It's best if she let one of us go. I don't want it to be you little brother."

Elena had gotten off work. It was a slow day. She had already wanted to go home. Matt had agreed to meet her in the Square after work. When she arrived, she saw him waiting on the bench. Matt smiled, seeing his friend approach him. The smile faded when he saw her eyes said something else. He knew something was bothering her as soon as she sat down. He could see that she had tired eyes, puffy from crying. "Elena, is everything okay?" As soon as the question had left his lips, Elena told him everything from start to finish. Once she was done explaining, Matt reached out with an arm and pulled her in for a hug. Elena had never been more than grateful for having a friend like Matt. "I don't know what to do. His flight is in a few hours and—"

"Go to him Elena." Matt interrupted.

"Damon! Wait." Damon had turned his head, seeing Elena run up to him. He was more than surprised to see her, especially after their conversation that ended on a sour note. Elena pressed her lips to his, wrapping her arms around his neck. She pulled away, gazing into his eyes. "You didn't give me a proper goodbye." she whispered. Damon saw that she had been crying. He hated leaving her in the state that she was in. It was his fault. While a part of him didn't want to leave, he had to. He reached out and touched her cheek, caressing it softly. He loved this woman, the woman who stood before him with her brown orbs gazing up at him. He could see the sadness in her eyes and how much it had hurt him to leave. "Come visit me in New York when you can, alright?" Damon smiled softly. The smile wasn't all there. "I have to go. Goodbye Elena." With his carry-on bag in tow, Damon bid his brother goodbye before heading to the security line.