|“|| Damon: Just you?
Enzo: I snuck off. Didn't feel like playing scissors, paper, stone over who was going to save your life.
Damon: That's very heroic of you.
Enzo: I don't leave people behind. Not my style.
The relationship between vampires Damon Salvatore and Enzo St. John. They were both test subjects for the Augustine Society, they formed a strong bond during their years of captivity. You could say that Damon and Enzo are a mixture of good and bad. Due to many set backs in their relationship, they aren't as close as they used to be and are currently frenemies, but they still remain allies.
They are known as "Denzo" by fans.
In 1953, when Damon was captured by Dr. Whitmore, he met Enzo. Damon is thrown into a cell where Enzo is first seen, he tells Damon to "pick yourself up, soldier" before introducing himself. After telling him that they have one glass of blood per day, he tells Damon he is doing it wrong; he is living for the moment when he should be living of the future, the future when they can extract their revenge. His revenge would be "killing Whitmore's dog and mailing it to his house", asking Damon to then picture his own.
Damon and Enzo's friendship grows through their time in captivity, Enzo is seen asking Damon about his interests, revealing his own is Jaguar cars which he can take out to impress women. Damon tells him that the one woman he was trying to impress was more of a "Horse and carriage" type of girl. After Damon asks about any women he has met, Enzo tells him about Maggie, a woman he met whilst in captivity. She knew nothing about the torture of vampires however when she found out, she couldn't bear it and left. Damon suggests the relationship between a vampire and human wouldn't of worked out and it was for the best, Enzo smiles and says "he needs a more positive outlook" before Dr Whitmore walks in asking who is next.
He heads towards Damon saying he looks as if he has more energy however Enzo quickly speaks, saying he is far more energetic, sparing Damon from the torture that day. As screams are heard throughout the basement, Damon angrily paces his cell. When Enzo is returned, bloody, Damon demands to know why they are doing this to them.
After the one night of the year they are let out of the cells, a New Years Eve party Dr. Whitmore hosts to show his findings, Enzo came up with a plan for their escape. As they are given one glass of blood, if one were to have two a day, the vampire could build up their strength for the next party so they would be ready to fight. After a game of "rock, paper and scissors", Damon wins and drinks Enzo's rations for a year.
One year later, Damon is pulled out from the cage although this time, after drinking Enzo's rations is able to break the chains. He kills Dr. Whitmore and the rest of the guests at the party, however a candle is knocked over and as Damon tries to break the cage bars, he cannot due to vervain. The flames begin to take over and as Damon realizes he cannot free Enzo, he shuts off his emotions before leaving.
Throughout The Vampire Diaries
In The Cell, Damon is kidnapped by Wes Maxfield and is thrown into the same cell he was in 1953, and reveals his dark past to Elena about how he met Enzo. Elena wakes up in a laboratory, where she meets another vampire who introduces himself as Enzo.
In Fifty Shades of Grayson, Enzo and Damon were reunited for the first time since 1958. Enzo tries to kill Damon in order to obtain a antidote for desiccation from Wes. Damon refused to fight Enzo and Enzo then desiccated mid fight. Damon injects Enzo with many antidotes and one of them works. Then, Damon reaches inside Enzo's chest and tells him he had to flip off his humanity to leave him. Enzo tells Damon that he was the most important person in his life and he ruined him and that he is just a monster and always will be.
In The Devil Inside, Enzo showed up at Damon's house with Aaron in a body bag. Enzo told Damon that he had done some "soul searching" and was quick to judge him. He told Damon that he wanted to see if the Damon he remembered was still there, to show him he asked Damon if he wanted to kill Aaron. When Aaron woke up instead of killing him, Damon snapped Enzo's neck and told Aaron to leave. Later, Enzo was lying in the road when Aaron stopped. Enzo said Damon was teaching him a game. After Damon and Aaron argue that Elena was too good for Damon and that he is a monster (which Damon confirms) he bites and kills Aaron much to Enzo's delight. "There's the Damon Salvatore I remember", and they both smile over Aaron's dead body, their friendship completely renewed.
In Total Eclipse of the Heart, together they've captured Diane, who works for the Augustine and compel her to talk all she knows about Wes Maxfield. When they get all the information from her, they kill her and are trying to find Wes on their own. Using Jeremy as leverage, a locator spell is used on Wes. Damon and Enzo arrive at the place where Wes is but are ambushed by travelers who are attacking them. While the Travelers are holding Damon and Enzo down, Wes infects Damon, turning him into an Augustine Vampire. Damon then tells Enzo that if what Wes injected him with what he thinks he did they're going to have a problem. At the end of the episode, Damon finds another test subject vampire who is bleeding and then begins to feel his body elevate at the smell and sight of his blood. Damon then violently feeds on the test subject to the point where Damon rips his head off. Damon then turns to a shocked Enzo seeing they have a problem then stares at Damon who stares menacingly back at him in shock of what has happened to him.
In No Exit, their friendship is tested as Damon is now an Augustine ripper whom feeds against his own kind (Wes's latest project) Enzo doesn't doesn't abandon Damon seeing as it as his fault his best friend is an vampire killer. Enzo turns anybody they come across as vampires for the soul purpose for Damon to feed. They prepare to leave the farmhouse for New York when Damon hears the telltale chanting of Travelers outside. They open the door and find they are stuck inside—and Wes Maxfield is there. Damon is his patient zero and he wants to see how long Damon can go before he feeds on his best friend. They're trapped. Enzo is worried seeing as Damon can't go eight hours without killing. Damon assures him he's not going to feed on him. Back at the farmhouse, Enzo chains Damon to a chair (with his permission). Then Enzo calls for back-up. "I told you your pride isn't worth either of our lives," Enzo says to Damon's objections.
He calls Stefan, but Stefan isn't near his phone and Katherine answers. Enzo catches her up to speed as Damon shouts in the background for them not to come. Katherine tells him to text her the address and they'll be on their way. He tells her he's under strict orders to kill Damon if he tries to feed on her. He's kidding but it gives her an idea. At the farmhouse, Damon is worried he'll feed on them if they come. Suddenly, there's a shot. Wes shot Enzo in the shoulder to see if Damon would get hungry enough at the smell of his blood to break the chains.
Damon busts through easily and attacks Enzo. Enzo tries to remain calm and yells at Damon to stop. Finally, Damon pulls off and starts retching.
Wes tells him the Travelers raised the acidity of his blood so Damon was essentially drinking hydrochloric acid. He'll allow Enzo to leave because he wants something from him. At first, Enzo insists on staying, but Damon tells him he tried to kill him once and he'll do it again. He yells at Enzo to leave and he finally does.
In While You Were Sleeping, Enzo had been searching for a cure for Damon and gives it to both him and Elena. Enzo also implies Damon was trying to set up him and Caroline, as she likes accents.
In Resident Evil, Damon and Enzo are playing pool with each other and so Damon can get over Elena. Elena calls him, but he ignores her calls, so Caroline calls him instead. He tells her to bring a witch and come over to the house to talk about it. They both arrive and there's an awkward silence, so Enzo decides to go to the library for a drink with Caroline so Damon and Elena can talk and to give them entertainment. Enzo and Damon then go to the house where Stefan and Elena are dreaming of and they meet Markos. Markos wants to talk to Damon alone, but Enzo tries to say differently so Markos tells him he won't find out about Maggie if he doesn't stay.
In Man on Fire, Enzo finds out Damon was the one who killed Maggie, not Stefan, and he decides to turn his humanity off as a way to cope with it. Unfortunately, unbeknownst to Damon, Enzo gets Stefan to pull his heart out so he would take the blame for killing him as revenge.
Stefan and Elena continue to hide the secret of Enzo's death in What Lies Beneath until Elena tells Damon the truth of Enzo's death, to which an angry and sad Damon punched Stefan in response.
Enzo does not yet know of Damon's death in Home as Damon sacrificed himself to save everyone.
In Yellow Ledbetter, it was revealed that Enzo has been searching for a way to bring Damon back, as he was asking witches around, Enzo joins Caroline in a road trip to pay Stefan a visit, after figuring out that Stefan wasn't searching for his brother, Enzo stabbed his hand with fork saying "What kind of a coward gives up on his own brother", then they both fought, and Stefan snaps Enzo's neck. Later, Enzo finds Caroline crying in the car because of the fact that Stefan had given up, Enzo gets angry when he sees her, and went back again to Stefan and killed his girlfriend Ivy, Enzo couldn't understand why Damon promised Stefan with a eternity of misery, but after seeing him giving up on his brother, he says that he doesn't see anything in Stefan that is worth caring about "But now I get it. You're not a brother to him. Brothers don't give up. So every time I see you doing anything that looks like you've done so, every time you try to start over in a life that's nothing but a lie, I will make you pay. I will be the one to bring you the misery you deserve.", then Enzo snaps Stefan's neck.
In The More You Ignore Me, The Closer I Get, Damon is captured by Tripp and is reunited with Enzo. Enzo tells him Stefan sold him out because he killed Ivy and Damon says that will do it. Both Damon and Enzo are then saved by Stefan so they won't die their original deaths since they crossed over the magical border of Mystic Falls.
In I'd Leave My Happy Home For You, Damon invites Enzo to Alaric's bachelor party and learns from Stefan that Lily is the one who turned Enzo into a vampire. Damon confronts Enzo about it and Enzo tries to persuade his friend that he shouldn't take the cure, that he would never want to be human.
Damon and Enzo's relationship falls into a frenemy relationship when Enzo chooses to side against Damon and side with his mother and enemy, Lily Salvatore. The two continue to have somewhat antagonistic banters throughout the season.
In One Way or Another, Enzo shoots Rayna Cruz with darts and takes Rayna before Damon could get to her. Damon later call Enzo and finds out that Enzo took Rayna because Enzo was using the huntress to help Bonnie Bennett. The two have a disagreement however, with Damon saying that he needs Rayna to get his brother Stefan back.
In Somebody That I Used to Know, Damon tags along with Enzo and Bonnie in order to get into contact with Rayna Cruz. Damon and Enzo bicker along the way before Enzo lets Damon see Rayna. After Enzo and Damon interrogate Rayna, they team up with Stefan and even Alaric to kill all the vampires on Rayna's hitlist. They help Rayna in order to protect Bonnie's life.
In Kill 'Em All, Damon and Enzo are continuing their goals of killing every last vampire on Rayna Cruz's Phoenix Sword-hitlist. They soon realize that Bonnie would be found before they take out every last one of Rayna's vampires. Damon gets another man to kill Rayna's vampires while Damon and Enzo help Bonnie by complying with the Armory until they can swap Bonnie and Rayna's lives.
In Requiem for a Dream, Damon and Enzo are first seen together debating on how to handle Bonnie's newfound Supernatural Huntress powers. They work together to try and convince an unconscious Bonnie to see past the Huntress side, but this is unsuccessful. Caroline is the first to be unsuccessful and becomes marked as a result of trying to get to Bonnie. Enzo and Damon try their best to help Bonnie see reason, but they are unsuccessful too and they share the same fate as Caroline as a result of trying to help Bonnie.
In Gods and Monsters, Enzo and Damon work together in order to save Bonnie's life. Enzo thanks Damon, along with Bonnie, over the phone for all his help. This possibly helps the two to grow closer in friendship. However, at the end of the episode, Enzo with Bonnie frantically tells Damon to not go inside the Vault in the Armory's building as Damon hallucinates hearing Elena's voice. After Damon is corrupted by The Armory's Monster, Enzo finds him in the vault, and he is shortly snatched by the Monster and corrupted. They somehow escape together, and go on a killing spree throughout the east coast, killing a total of sixty people over three months.
- Enzo: "Morning, sunshine."
- Damon: "Enzo? Well, this brings back memories."
- Enzo: "I'm glad to see you found a way back, mate. 'Fraid it's going to be a short reunion, though. We're headed for Mystic Falls, known for it's bridges, quaint small-town charm, and a really big vampire bug-zapper."
- Damon: "Stefan could've told me there was a hunter in town."
- Enzo: "It probably slipped his mind because he's responsible for my return to incarceration."
- Damon: "Why would he do that?"
- Enzo: "Probably jealous of my accent. Eh, maybe he did it because I killed his new girlfriend."
- Damon: "Yeah that'll do it."
- Enzo: "See? Now that's what I call a missed opportunity. Perfect time to tell your brother you're hanging up your fangs for a pair of khakis."
- Damon: "No idea what you're talking about."
- Enzo: "Yes, you do. I might have plied Alaric with enough alcohol to slur the news into my ear."
- Damon: "Well, you are the last person who gets to criticize me for withholding information, my brother from the same mother. You ever gonna tell me Lily turned you?"
- Enzo: "Yeah, once you mastered the art of returning phone calls."
- Damon: "I've been busy."
- Enzo: "What, with the prospect of taking the cure? No point in agonizing-- you won't go through with it."
- Damon: "Says who?"
- Enzo: "You! You're selfish, Damon. Being human isn't what you really want. I mean, don't get me wrong, I like that about you. A man should be consistent. But, take it from someone who you left to burn to death in order to save your own skin-- no one changes that much. Not even under the magical influence of Elena Gilbert. Anyway, cheers, mate."
- During their time captured by The Augustine Society, Enzo was prisoner 12144 and Damon was 21051.
- They were both soldiers at some point.
- Damon fought for the Confederate Army in the American Civil War.
- Enzo fought in World War II.
- Enzo was the reason that Damon switched off his emotions in 1958 because he couldn't get him out of his cage and had to leave him behind in the fire.
- They are now best friends after Damon killed Aaron proving to Enzo that the Damon he knew back in the 1950's is still in there.
- In Season Six, Enzo is searching for a lead to get Damon and Bonnie back.
- In The More You Ignore Me, The Closer I Get, Damon and Enzo are both captured by Tripp and reunite when Damon wakes up in the van.
- The actors Ian Somerhalder and Michael Malarkey, who play Damon and Enzo, are best friends in real life.
- Enzo was turned by Damon's mother Lily.