Do you ever look back on your life and realize that at every crossroad, you picked the wrong direction?

You took the longer way around because you were convinced it was shorter, you chose to major in something that you could never possibly make a career out of, you chose the wrong girl…

Yeah, Damon had never felt that way...or at least that's what he tried to drill into his thick skull.

He was finally at the point in his life where everything fell into place-wife, kids, a big house with a white picket fence-Damon had checked off everything on the list. And he was happy.

"Damon! We have a situation!" Andie yelled.

She was upstairs giving a bath to their daughter, or at least attempting to. He made his way up the stairs and caught their naked two year old red handed as she ran into him naked with soap dripping down from her wet curls to their carpet.

"Now, where do you think you are going, young lady?" He said. Damon tried to be stern with her, but her bright blue eyes were making it hard to stay mad at her.

He marched his daughter back to the bathtub where his wife was waiting for him, her shirt completely soaked from being in the splash zone.

"Thanks."

Andie put their daughter back into the bathtub, and Damon gave her a light kiss on the cheek before descending back down the stairs. He went into his home office and shut the door behind him.

Yeah, Damon was happy with the way his life had turned out. It was moments like this with his wife and child that made him remember how lucky he was-so many others never even got the chance to live a life as fulfilling as his.

He pulled out a key from his pocket and unlocked a drawer in his desk. His hand blindly searched underneath a stack of manila folders for...his hand wrapped around the tiny box.

Damon brought out the tiny velvet box and slowly opened its lid. He stared at its contents-it was his mother's ring, a large oval diamond that sat on a simple silver band. He gingerly took it out of its prison and held it between his fingers, letting the memories flood his mind.

Seven years ago…..

"Damon, I need you to promise me something."

His mother weakly tried to prop herself up as she laid in a hospital bed. He took her hand and squeezed it before meeting her icy blue eyes that matched his.

With wobbly fingers, she slid off her wedding ring and put it in his empty hand. "I want you to give this to the love of your life, whoever she may be."

A tear slid down her cheek. "I'm not going to be there on your wedding day, but with this ring, you'll have a piece of me there with you."

"Mom, you're always going to be with me. No matter what." Damon told her.

His mother nodded her head, and she pulled him into a hug. "Just promise me."

"I promise." He whispered.

Present Day

Damon wished that his mother could see him now with her daughter-in-law and grandchild. He knew that she would be happy for him, but he couldn't help but feel that she would be a little disappointed.

Against her wishes, her ring sat on the bottom of a locked drawer in his office. This was the first time that it had seen the light of day since…

The memory of her haunted him everywhere Damon looked. She was in his morning coffee-black with two packets of sugar just like she liked it. She was the flash of the long, brown ponytail that swung as a runner ran down the street. She was his mother's ring that sat in his desk drawer.

He had always planned on giving it to her before...well, before it was over. It didn't feel right to him sitting on anyone else's finger-including his own wife's.

Damon put the ring back in its box and tucked it back into the bottom of the drawer. He twisted the key in the lock and relocked the drawer and the memory of her.

"Liam, I can't do this anymore."

He nodded his head and walked out of her apartment, shutting the door a little too hard on his way out.

Elena sighed and walked over to her liquor cabinet usually remained untouched. She usually preferred a glass of wine, but at the moment, bourbon suited her just fine.

She poured herself a glass of a bottle that he bought for her years ago. Elena ignored the pain of that realization with the burn of the dark liquid down her throat.

Her breakup with Liam marked her fifth failed relationship in the span of four years. What had she done in a past life to give her such bad luck in this one?

She downed the rest of her glass and let the buzz overtake her mind. With every new relationship Elena entered, the tiny voice in the back of her head told her that something wasn't right. Sometimes it took longer, but with Liam, the voice only waited two months to remind her.

This time, the voice had been so specific that it shocked her-he isn't Damon.

The pain of losing Damon consumed her at that moment in a way that it hadn't in years. The little pieces of her heart that she had worked so hard to stitch back together, unraveled, leaving the pieces scattered around her.

Elena remembered hearing the news that he was engaged three and a half years ago, exactly six months after they had broken up. His brother, Stefan, had told her the news, his eyes downcast. It had felt like someone had taken a knife and used her heart as throwing practice.

She hoped that he was happy-she truly did. As selfish as she wanted to be, Elena knew that she couldn't. To hell with her happiness if he had his.

She poured herself another drink, and the faint buzz in her mind became stronger. Did he ever think about her? Did he feel even an ounce of the pain that she felt?

Elena knew that speculating would only make the pain worse, but she couldn't help it. But there was one thing in her drunken mind that she knew for sure-she needed to let him go.

I'm still working on the next chapter for Dream a Little Dream of Me, but I've been stuck in a loop of watching Nian edits and the inspiration hit for this story. I respect Ian and Nina with their respective relationships, but it's hard not to feel like they made a massive mistake. I'm sure that a lot of you have also noticed that Ian has seemed more cold and distant since their split, and it seems like Nina hasn't had a super serious relationship ever since. We'll never know truly how they feel about each other, or if the rumor that they ended their relationship because Nina wasn't ready for marriage is true, but I think that it is undeniable how much more chemistry they had with each other than with their other partners. Thanks for coming to my Ted Talk :) I would love to hear your opinions on the subject