1977

Damon was having the time of his life. Enzo had left to find Maggie, the two of them are traveling the world together. But the trip was soon cut short when Enzo learned Maggie never truly loved him, she just wanted to be turned. She did care for him, just not as much as he did for her. They soon parted ways, Maggie going back to the States and Enzo continued to travel. He had promised to meet up with Damon eventually but was enjoying his freedom.

New York never slept and neither did Damon. He partied every night, drank from the locals, and just had fun. He knew Stefan had heard about his activities when he spotted Lexi watching him from across the bar he frequented. He came to the conclusion this was one of the events he could not stop but change. He waited for the older vampire to approach him, "Took you long enough. Did my brother send you? Are you here to ruin my fun?" Damon never liked Lexi but accepted that she helped Stefan at times. Although now things are different, Damon knew how to help his brother with the Ripper. It was only a matter of time before they saw each other.

Lexi leaned on the bar next to the eldest Salvatore, "Stefan voiced his concerns about you. He thinks you've gone off the deep end. I told him I would check up on you. So, here I am." Damon downed the shot of liquor before slamming the glass onto the bar, "You didn't have to. I'm fine. Just having a bit of fun with the locals. I haven't killed anybody in...too long." Lexi sighs, "Stefan was worried enough to convince me to find you." Damon took another shot, "Well, you can tell Stefan that I am fine. I don't need a babysitter." "Are you still sour about the 40s?" The older vampire asks.

Damon moved away from the bar, not even bothering to answer. Lexi follows him out onto the street. Damon turns to face her, "Look, I get why you stopped me from going with my brother. But why are you really here? As far as I'm concerned, I have not misbehaved enough to bring attention to myself, so why are you here?" Lexi shrugged, "I owed it to Stefan." "Well consider your debt paid and leave me alone," Damon whooshed away from Lexi. He didn't see her again, they never had sex, and he never trapped Lexi on the roof of the bar.

1994

This is the year Damon dreaded. It marked one of THE biggest regrets of his life, killing Gail. He could feel Fate's hand crushing his heart as he walked up the steps to the Salvatore Boarding House. Damon was going to avoid coming back to Mystic Falls for another decade, but Fate had other plans. He was supposed to be here. That does not mean the same things have to happen.

Damon had arrived on May 08, much later than last time. He hesitantly rang the bell and waited for his nephew to open the door. Soon, a young and very much alive Zach Salvatore opened the door, "May I help you?" Damon smirked, "Hey...Zach, right? I'm looking for my brother, Stefan." Zach's eyes widened at the realization that the 'unstable' brother was standing in front of him. Before Zach could say anything Stefan was at the door, "Damon? What are you doing here?" Stefan stepped past Zach and closed the door behind him.

"What? I can't come visit my little brother?" Damon tried to seem nonchalant but in reality, he wanted to grasp his brother in a hug and not let go. Here he was, Stefan was standing in front of him, alive. Stefan shook his head, "Why are you here, Damon?" Damon sighed and became serious, "I need to talk to you. Can you get our nephew to invite me inside? I promise to be on my best behavior." Stefan wasn't convinced, especially after Lexi informed of what happened in New York. He'll just have to keep an eye on his older brother.

Soon, Stefan and Damon were sitting in Stefan's room. He could tell Damon was different. Normally the elder Salvatore brother would be snarky and rude, but Damon seemed to be anxious, if anything. Damon stood and started pacing the length of the room. He would stop, look at his brother before starting to pace again. "Just spit out, Damon," Stefan was getting anxious himself watching his brother pace.

Damon ran his hand through his hair, "Back in 1953, I came back to Mystic Falls. I was here for maybe a day before Joseph Salvatore spiked my drink with Vervain. I killed him and then was injected with a stronger dose of Vervain and taken to Whitmore where I spent five years being experimented on. I had a cellmate, Enzo. Every New Year's Eve, the two of us were put on display during the celebration. In 1957, Enzo and I came up with a plan to escape. One of us would have both rations of blood throughout the year to gain enough strength for both of us to escape. On New Year's Eve 1958, I broke out of my chains, escaped the cage and killed almost everyone in attendance. A fire broke out and I had to get Enzo out before he burned to death."

Damon stopped to garner Stefan's reaction. He had gone pale and looked sick. Stefan asked, "What kind of experiments, Damon?" Damon scoffed, "Let's just say I know how long it takes to grow my eyes back with little to no blood." Stefan swallowed the rising bile and nodded his head for Damon to continue, "Now, here is where it gets complicated. In the original timeline, I did leave Enzo after switching off my humanity. I have lived this life already. I died a human in the year 2025, I was shot in the head by my wife. I was expecting to see you in the Afterlife but instead I was sent back to New Year's Eve 1958."

"Time travel? No, I don't believe you," Stefan doubted his brother's story. "Well, believe it brother. Because there are rules that I have to follow. I can only tell two people. I have told Enzo and now you. And Fate determines if certain events have to occur. I was going to stay away from here until much later, because on May 10, 1994, I killed Gail. That was what happened last time, and I am trying to prevent it this time by not coming back to Mystic Falls, but Fate wasn't having it. I can only affect the outcome."

Stefan stood in front of his brother in a threatening manner, "You will not hurt them, Damon. Gail is pregnant, she is family." Damon shook his head at his brother, "I promised you I will be on my best behavior, and I meant it. I have no intention of hurting anyone, but I'm supposed to be here. Fate, herself, brought me here." Stefan looked down, his eyes pivoting back and forth as he ran through different scenarios, "What happened last time? Tell me everything."

Damon started pacing again, "I had my emotions off since 1958. In 1977, you sent Lexi to check on me. Which was cowardly on your end, you should have been the one to help me and I resented you for it. You did the same thing this time. The main difference is I didn't flip my switch. I was still a dick, still am. Like I told her, I don't need a babysitter. Last time, I tricked her and left on the roof of a bar for her to burn in the sun. This time, I told her to get lost. Now, here I am two days before an event that was my biggest mistake and worst regret. When I want to be on the other side of the country ripping the head off a sociopath that murdered his entire family because he was a siphon.

"On May 10, his father and what's left of the Gemini Coven banished him to a prison world instead of killing him. When he gets out of said prison world, he sets off a domino that affects all of us. But since I can't leave here until the 11th, I can't kill the guy. I tried several times to turn around on my way here, but Fate wouldn't let me. So, here I am. I'm going to keep myself busy and away from Zach and Gail, so little Sarah can have both parents this time." Damon was sprawled on Stefan's bed.

Stefan cleared his throat, "Was there anything else that happened while you were here last time?" Damon propped himself onto his elbows, "I befriended Liz Forbes, then I compelled her to forget she ever met me before I attacked Gail." It was like a light bulb went off. Damon jumped off the bed and grabbed his leather jacket, "I'm going to say 'hello' to the future sheriff." Before Stefan could stop his brother, Damon whooshed out of the Boarding House. Stefan just hopes Damon will keep his word.

Later that week, Damon exhaled a sigh of relief when the 11th rolled around, and Gail was still alive. He returned to the Boarding house after meeting Liz and hanging out. Damon wanted to tell her about her future but knew he couldn't. He'll just have to watch out for her later on when he returns to Mystic Falls. He burst into Stefan's room, "Oh, little brother." He smirked when he heard the shower running. Damon whooshed into the bathroom and flushed the toilet. The girly shriek that followed had Damon dying of laughter. Stefan rinsed the soap from his eyes as he yelled, "Damon! Not funny!" Damon tried to catch his breath while still laughing, "Yes, it was."

Damon promised he would behave and not hurt anyone, that does not mean he couldn't torment his baby brother in other ways. Stefan eventually got out of the shower and got dressed. Damon had come into his little brother's room to bid him farewell, "I'm off to cause mayhem elsewhere. TTFN, that's TaTa For Now." Damon patted his brother on the back then whooshed to his car and left. Stefan couldn't help but smile and think he hasn't lost his brother.

2007

In North Carolina an obsessed Isobel Flemming approached a random vampire and was turned. Damon was nowhere near Duke University. Instead, he was in Florida soaking up the Miami sun and stalking a certain untriggered werewolf. When Katherine showed up, Mason had already left Florida on an all-expense paid trip to Hawaii courtesy of one Damon Salvatore.