After her flight, Elena had arrived in New York. She would've never imagined hopping on a plane for just anyone. It was always Damon. In her heart, she knew that he had been the one who filled her life with happiness again, especially after the loss of her parents. Elena grabbed a taxi to take her to Damon's apartment. Upon her arrival, a car was sitting just outside. A car that she deemed unfamiliar. It had only been a mere 24 hours since Damon's departure, and he had someone over. Elena couldn't believe this. She wasn't known to assume such things, except she couldn't help herself. She approached the door and buzzed in. She headed up to the floor where his apartment was located and knocked on the door. She waited a few brief minutes before meeting eyes with a woman. The woman who stood before her had green eyes and brown hair. "I didn't think we were expecting company." said the woman. Damon was just crossing behind the woman and stopped in his tracks, seeing Elena at his doorway.

"Well, I wasn't expecting Damon to have any guests over." Elena crossed her arms. Somehow, she felt intimidated by the woman. She silently assessed that the woman must be around Damon's age. There was something eerily familiar about her. Elena couldn't put her finger on it. "Elena, this is Isobel Flemming, your birth mother, who also happens to be a close friend of mine. She's the one who introduced me to Alaric." said Damon.

"My mother?" asked Elena. Elena was nothing more but confused now. She must've assumed wrong. "After all these years, you failed to tell me that you're still in contact with her?"

"Elena, let me explain-"

"Why did you leave Mystic Falls?" Elena interrupted. Her eyes still locked on him. Damon didn't know where to begin. He thought about this moment countless of times in his mind during his flight back to New York. It wasn't until earlier today when Isobel had decided to stop buy unexpectedly. He hadn't expected for Elena to hop on a plane and follow him. It seemed out of character. "You deserve much better than me Elena." Damon could tell that what he had said wasn't the answer she was looking for. He could see that she was hurt and even more mad at him. "I just think that... I thought that you would be happier there being with your family and friends. It would've been too much for me to ask you to move back to New York with me, and when you found out that I had asked Caroline to marry me, I thought that you wouldn't forgive me. I've done a lot of stupid things in my life, especially when Alaric passed away. I saw you before I even had the chance to get to know you. At the time, I talked with Isobel. She was the one who told me to keep my distance from you, only because she knew the kind of person I was.

"She knew me in college, and I was a different person back then. I was reckless. I allowed myself to mess around with other girls, who meant nothing to me until I met you. I screwed up when I met Caroline, when I started talking to her behind your back. I shouldn't have done that. I spoke with Jenna about us, about how I messed up. I told her I wanted to fix things with you and I, except I didn't. I just flew here, and I'm telling you that you don't need me to be a part of your life." Elena listened to what he had to say. She didn't fly all this way to see him, just to hear him tell her that she deserved better. She reached into her purse and took out the small box before handing it to him. Damon knew what was inside. He remembered the very day he had gotten it.

"Tell me why I have to go with you?" Stefan had flown to New York to see Damon. The two were driving down the street to the nearest jewelry store. The two brothers haven't seen or bonded with each other since Damon's last visit to Mystic Falls. Besides, it was good to be able to spend some time with his little brother. "You'll see." Damon smiled. Damon parked his car in front the jewelry store. The two get out of the car and enter the store. A woman approached them and asked if they needed some help. "I have a sample picture of a ring that I want to give as a gift." He had taken the picture out of his pocket and handed it to the woman. She looked at the picture and told him to wait just a few minutes. Stefan had only seen a glimpse of the picture before asking his brother about it.

"That's an engagement ring." said Stefan. "Who is it for?"

"Just someone I like." Damon didn't want to say the name. He knew about his brother's former relationship with Elena. He knew how Stefan felt about her, considering that their relationship had ended just recently. While though Damon had only met Elena this past semester, he immediately pictured a future with her.

"Did you-"

"No, I didn't. Jenna gave it to me before I flew here." said Elena. "I should go."

"Before you go, stay for dinner at least. Also, wouldn't you want to get to know your birth mother? I know you probably have some questions about your parents... your biological parents." Damon slid the box into his pant pocket. Elena couldn't deny Damon's statement about wanting to get to know her parents. She did have many questions to ask, especially why her birth parents had given her up for adoption. Elena agreed to stay, which allowed for her and Isobel to spend some time bonding. Later that evening, Isobel had bid her goodbye, leaving Elena alone with Damon in the apartment. Damon had set the dinner table, decorations and all. "I know earlier I said you don't need me in your life. It's just because I know you've been through a lot. You've always made decisions independently, regardless of what everyone tries to tell you. I know you may not listen to me because knowing you, you will tell me otherwise. You will tell me how you feel. You will tell me that your life is meaningless without me. I'm going to tell you that you could be right. Now that we're in the same room, all I keep thinking about is how empty my life is without you. As soon as I left Mystic Falls and landed here in New York, I started to realize that before meeting you, I didn't have much of a life. I ran around doing what I did in college. When I saw you enter my classroom on the first day, I saw a remarkable resemblance to Isobel. You're much more different than her of course.

"I don't regret meeting you. However, I do regret losing you. I spent so much time trying to push you away, to make you see how wrong I am for you and how you are meant to be with someone else. I wasn't deserving of your love, deserving of everything that you have to offer. I will stand here and tell you how wrong I am for you. But I will also stand and tell you how many times I am sorry for leaving you. I am sorry for hurting you the way I did. I'm sorry for not telling you the truth about Caroline and I. I am sorry for not being the best man I can be. I will keep on trying every day to make up for everything that I have done. I will show you in every possible way that I can be the man you want me to be, to not be a selfish and heartless person. I love you Elena Gilbert, and I have always loved you since the very first moment I knew I was in love with you. You have always been the very person that I want to spend my life with. No one else can compare to you, and I'm hoping that you'll forgive me. I'm hoping that you'll allow me into your life again because leaving you was the worst mistake I have ever made." Damon took her hands in his. "Before you say anything, there is something I have to ask."

"How is New York treating you?" Elena was in her dorm room Skyping with her aunt, Jenna. From time to time, she would also talk with her friends. She wasn't comfortable with telling them about Damon just yet. The two had only talked a handful of times. Mostly it was either between classes or passing. She wasn't sure if Caroline or Bonnie would inform Stefan about her seeing someone else. As much as she trusted her friends, she didn't trust them with this new information about a guy. "It's been good. I'm missing home." replied Elena. Jenna reassured her that everything will work out just fine and told her not to worry. Elena wanted to believe her aunt. Just before Elena opened her mouth to say another word, a knock sounded at the door. She knew that it couldn't have been her roommate. She told Jenna that she will talk with her later and ended the Skype call to answer the door. Once she opened the door, Elena was startled to find herself face to face with Damon. She was about to question him when he had started to speak. "Look, I don't have much time. Are you available this Saturday?" asked he. Elena said she was. Damon flashed his million dollar smile before saying that he'll stop by to pick her up around 6:30 that Saturday for dinner. Before Elena could say anything else, Damon had already turned to walk back down the hallway.

Just like that day, Elena had only nodded in reply to his answer and stayed silent. She waited patiently for him to ask his question. Today had been such an eventful day. Elena had gone over what had happened since the moment she stepped off the plane. As soon as she had arrived at his apartment, everything happened in a blur. Elena still couldn't believe that she had met her birth mother, Isobel. She went over the conversations the two of them shared and how many more questions she wanted to ask Isobel. Elena had wanted to know more about Isobel herself and about her father, John. Then she went over what Damon had been telling her, that he wasn't the right man for her. Who was he to think that she deserved better? Did she? Elena couldn't answer that. She went over the many possibilities about what her life would've been like if she ended up with Stefan, or Matt even. Though in both situations, she found it ludicrous. She couldn't try to imagine her life with either of them. She couldn't see herself raising a family with either of them, living in a house, or even growing old. As much as she had loved them for who they are, both of them were a part of her life that she had decided to leave behind in Mystic Falls.

From the very day she met Damon and had gotten to know him over the last four years, Elena had truly fallen in love with him. She imagined spending the rest of her life with him, regardless of their age difference. She looked into his eyes and knew right then in there her future with him. She imagined that they would live together, probably somewhere in the suburbs in New York. She pictured herself with a white fence, green grass, and two children just running around in the yard. She would be sitting on the porch swing with Damon. He would be sipping an ice cold beer with his arm wrapped around her shoulders. Her head would be comfortably rested in the perfect spot, the nook of his neck. Elena could picture it all with him, as her heart had chosen. "Will you-"

"Yes." Elena interrupted.

Damon chuckled, "I didn't even finish my question."

"I don't care. No matter what the question, I'll always say yes." Elena gazed up at him with her brown eyes.

"Well, I guess that means..." Damon pulled out the box Elena had handed to him. "You're saying yes to this?" Inside the small box that Jenna had kept from Elena was a beautifully crafted diamond ring. Elena hadn't been expecting the ring at all, even though she had always been curious about what was inside the box. She was only told not to open it. Even when she got home, she had immediately handed it off to Jenna because she did not want to be tempted. "Damon, it's-"

"This is my mother's ring. When she passed away, my father kept it. It was intended to be given to Stef, but unfortunately, I'm the oldest. I tried to look in jewelry stores to find a ring that would be perfect for you. It wasn't until I was cleaning out my dad's things and found the ring stowed away in my mother's jewelry box."

Elena kissed his lips. "Don't you dare buy another ring. I would be honored to wear your mother's ring."

"If she were still alive, she'd love you Elena Gilbert." Damon smiled, sliding the ring onto her finger.