Reinette : Clarisse du Volde was one of the first vampires Damon ever met while he was still very human. After being injured on the battlefield in 1863, she was one of the nurses he encountered in a Confederate field hospital. He was asleep when he heard sounds that frightened him, paralyzed with fear he opened one eye to see her put a fellow soldier out of his misery because his injuries were so bad. It didn’t occur to him what she was until they met again in 1920 in Chicago. Damon was shadowing Ripper Stefan when he saw Risse again in the speakeasy owned by a witch named Gloria. It was then that Damon and Risse became friends.
Ignacio: While Damon and Enzo were hunting down offerings for the Siren Sibyl, Damon came face to face with Ignacio the first time. While it would have been easy to just snatch and compel him to be a victim, something about Ignacio made Damon let him go. Later Damon figured out why he couldn’t turn Ignacio over to the Siren. It was because Damon saw himself in the other man. This spark created by the encounter with Ignacio gave Damon that first push to actually try to break free from Sibyl’s control.
Ardent: While Enzo and Damon were captured by the Augustines, the two would actually envision themselves in other places to escape the mental torment and the physical torment of the place. In one of these mental vacations they took, they were inside Enzo’s mind when Enzo taught Damon how to play the guitar. In another mental vacation, they were in Damon’s mind where Damon showed Enzo his secret love of the writer Edgar Alan Poe. However after the Augustines cut Damon’s chest open so he could see his own heart beating, he could never read The Tell Tale Heart again and neither could Enzo.
Mary Savarese: Damon's nickname Ol' Blue comes from Mary because of his blue eyes obviously. Damon knows that Mary truly admires his car even with all the kidding aside. What Mary doesn’t know is that if something happens to him and he dies for good, he’s left her his beloved car in his will. Damon does not have a sister by blood. He’s got Stefan and an older half brother that died a long time ago. He considers Mary the closest thing to a sister he’s got.
The Fox: While Stefan and Lexi went to a Bon Jovi concert in 1987, Damon considered himself a part of the Kiss Army. Damon actually went to a Kiss concert in 1987 where he compelled himself a backstage pass. While mingling with the band, he met Eric Carr the band’s drummer at the time. The two got along so well that Damon actually flipped his humanity switch back on for the first time since 1958. There was a hunter named John Winchester that was tracking Damon down at the time because of all the terrible things he’d done at the time. Eric helped Damon escape. The two became good friends at the time with Damon promising to turn Eric if he ever wanted to live forever.
Inventor: Damon met Nikola Tesla at that speakeasy that Gloria ran in Chicago in the 1920s. Turns out that Tesla and Damon hit it off brilliantly. He even helped Damon break into Stefan’s secret apartment in Chicago when Damon was trying to get closer to his brother without being seen. Having a Ripper for a brother was lousy. Having Tesla as his first drinking buddy as a vampire made an everlasting impression on the older Salvatore brother.
Good as hell: What Caroline doesn’t know is that Damon did actually meet her in 1994 when she was a toddler. It was the day of the big solar eclipse. Stefan had compelled Liz to go away and forget them, but Damon being who he was, went to the Forbes home anyway. When he saw Caroline in her playpen, he had an attack of conscious and couldn’t do it. He knew who she was when he came back to Mystic Falls fifteen years later but didn’t say a thing. He did blame himself for the fact Katherine killed Caroline turning her into a vampire. Caroline’s blossoming into a stronger person as a vampire meant the world to him. Damon will never admit it, but he is proud of the woman she became and thinks she’s the best mom he knows
Hope: While Damon isn’t exactly fond of the Mikaelsons, he does actually like Hope. That “hint of the devil” in her eyes (as Klaus put it) also reaches through to Damon. He calls her Sprite because she’s mischievous and that amuses the hell out of him. The two of them actually hid the key to Alaric’s liquor cabinet for a whole week. Best. Prank. Ever. If anyone ever hurt Hope, then not only did they have to deal with the Mikaelsons, they’d have a very murderous Uncle Damon to deal with in the process too.
Unconditional: When Josie and Lizzie were kidnapped by Seline, Damon and Sibyl did find them, but Damon stayed close to make sure nothing happened to either kid. He just let the Sirens think he was on their side when it came to the kids, but neither one was in any sort of danger. While they were in that hotel waiting for Cade, Damon made goofy faces just to make the twins laugh. While Lizzie looked at Damon like he had three heads, Josie laughed at him. That was the day that Damon bonded with Josie. Damon also was the one whom he shared his “love” for baking over the years. He made her some of his pancakes when stopping by the School for visits. When she was old enough she actually baked him some Christmas Cookies. He considers her a niece even besides the fact that Caroline was his sister in law. It was more because she is Alaric’s daughter.
“When people see good, they expect good.”