They’ve been together all summer, and Damon and Elena are very happy about it. Damon assured Elena that he would watch out for Jeremy while she was away at Whitmore. When Katherine unexpectedly appears and asks him to keep an eye out for potential threats, he agrees to do so. She calls Damon up while pretending to be Elena and fills him in on Jeremy’s troubles at school. Fortunately for Jeremy, Damon convinces the headmaster to reduce the punishment to three days. Sadly, they quickly learn that this is just a symptom of much deeper issues.

Damon

To meet Damon, Silas enters the pub posing as Stefan. While he’s there, he’s only listening to Damon’s thoughts and not contributing anything to the conversation. With the data he required in hand, he bade farewell to Damon, patted Jeremy on the back, and left for the Salvatore Boarding House. Damon tells Jeremy to secretly transport Katherine away from the scene after he and Jeremy arrive just in time. Silas must now explain to Damon in a nutshell why he resembles Stefan and reveal to Damon his actions with Stefan. Damon then decides to contact Jeremy to tell him about his about-face. In the future, Jeremy is about to die. Damon finally reaches him in time to revive him with vampire blood and a supportive embrace. And Damon keeps quiet about what occurred to Elena.

Damon’s gratitude to Liz

Damon enlists Sheriff Forbes’ aid in his search for Stefan in True Lies. After that, he’s on the phone with Elena when she runs into Silas (mistaken for Stefan) on campus. Damon attempts to reassure Elena it’s not Stefan, but Silas forces her to hang up. After hearing that Silas is with Elena in her Stefan disguise, Damon rushes to Whitmore to see Caroline. Caroline informs him about Elena’s persistent fear of being found out as Stefan’s imposter, and Damon agrees that they must go in search of Elena.

An intense embrace between Elena and Damon

Damon interrupts Elena and Jesse’s conversation by knocking Jesse out. Damon realised that Silas had used his mind control ability over Elena, so he did what he could to make Elena fight the “rage” by thinking about her concerns about Stefan. Elena then took him back to her college room, charmed him in order to bind him to a chair, and was ready for the murder. Damon later revealed to her that he had recovered Stefan’s daytime band from Silas the day before. And then Damon said that even though he is confident in their relationship, he still finds it annoying that she has clairvoyant nightmares about her ex-boyfriend. Elena kissed Damon and said she would still adore him even though they were going to save Stefan. Following that, they engaged in an intense embrace.

Damon and Elena, accompanied by Katherine, go looking for Stefan in Original Sin after both of them have a premonition about him. Elena and Damon’s trip is ruined by Katherine’s constant relationship-related teasing. Damon and Elena arrive at Jo’s tavern, the location from their dream, and leave a dozing Katherine in the vehicle.

During a visit to Jo’s pub

A bandaged Jo is located in the tavern. She tells Damon that Stefan attacked her and set fire to their apartment before Qetsiyah tossed him into a vehicle. In addition to directing them to the shack, she also reveals that she has identified the truck’s owner. Damon takes the liquid she offers him before realising it contains vervain. Nadia walks in and says that she would kill Jo if she didn’t. In the aftermath of a violent altercation with Nadia, Elena takes it upon herself to rescue Katherine from Nadia while Damon searches for Stefan. The two share one last passionate embrace before Damon warns Elena not to put her life on the line to save Katherine, saying that the latter is not even worth a single strand of Elena’s hair.

Damon in his shack

As Damon nears the shack, he sees Stefan bound and gagged on a chair. In vain, he attempts to set him free. Stefan says that Qetsiyah has returned. Qetsiyah reemerges and informs them that she plans to connect Stefan and Silas in order to neutralise Silas’s psionic abilities. Damon is sceptical, but Stefan goes along with it. She casts the magic and the enchantment’s heat starts to damage Silas’ head. It appears that Stefan has passed out. Even after Damon’s best efforts, he remains asleep. Qetsiyah tells Damon that he will come to in time and then goes on to say that his relationship with Elena is doomed. She explains how the reincarnated doppelgangers always end up together, in love, and victorious because that’s just how the world works. Damon can leave Stefan with her, she tells him, so that he can keep seeing Elena in peace. In spite of this, Damon plans to murder Qetsiyah, but she manages to put him out. As Qetsiyah departs, Elena walks in and immediately proceeds to be with Stefan, completely ignoring Damon. Damon seems to have been wounded by this.

At the Salvatore residence, Stefan is still out cold while Elena thanks Damon for being such a wonderful sibling. Damon remains silent. At the lodge, Elena inquires as to what Qetsiyah said to him. Damon informs her how she told him that he and Elena don’t stand a chance because the forces of the world are conspiring against them. Elena retorts that Qetsiyah is insane and that she will not allow Silas’ 2,000-year-old ex-girlfriend to disrupt her relationship with Silas. Damon informs Elena, “You are my existence, and no foolish notion of fate is going to keep me from loving you or being with you or making a future with you.” Elena is so moved by his words that she moves in for a kiss, but they are cut short when Stefan awakens up and insists he has never heard of either Elena or Damon.

Damon and Elena

While reading For Whom the Bell Tolls, Damon is assisting Stefan in recalling his past. Damon finds it hilarious when, during a journey with his brother, Stefan thinks that Damon is the responsible one and he is the carefree one. Damon crashes the vehicle, at which point Stefan sees he was wrong about Damon being the entertaining one. Elena pays them a call the following day at the restaurant, where she and Damon have a lengthy conversation about how to handle Stefan. Damon is paying respects to his ancestors at the Salvatore cemetery by striking the bell when he receives a text message from Jeremy asking to meet with him privately.

Damon embraces Jeremy.

Jeremy is attempting to break the news to Damon back at home that Bonnie has passed away. Damon gets the gist of what he’s getting at when he says, “No one can be called back from the grave without repercussions.” Even though Damon urges him not to, Jeremy eventually admits that Bonnie has passed away. Damon is indignant and marches furiously towards Jeremy as if he were going to strike him, but he turns around and embraces his friend instead.

While Damon is telling Elena about Bonnie’s demise, Elena contacts him to locate Stefan. When they return home, they discover Stefan has returned but is still angry that they didn’t inform him about their relationship. In an effort to restore Stefan’s recollection, Elena reveals to Damon that they urgently require Bonnie, prompting the latter to deliver the devastating news of her death. After that, Elena is inconsolable because she can’t find a suitable outfit for Bonnie’s burial, and she sobs into Damon’s shoulder, pleading with him to never make her go through that again. Damon gives her a comforting embrace to ease her anxiety. Damon comforts Elena at the burial for their mutual friend Bonnie.

Damon, at Whitmore College.

After Elena avoided him for as long as possible, Damon finally tracked her down at school in Monster’s Ball so that they could attend the Whitmore History Dance together. For one night only, students dress up as historical characters, and the college’s complete collection of relics is on show to the public. Damon has already informed Jeremy in Mystic Falls of his desire to collaborate with Silas. Because Silas is so intent on dying so that he can be with his true love, it would make sense to use his mortality to do the same for Bonnie and Elena. True harmony is prized by all of nature. Once Silas takes the remedy and gains his witchy abilities, he may be able to cast a charm that allows him to trade places with Bonnie. You can’t put your faith in Silas, and there are repercussions for misusing sorcery, even when reviving someone. Despite her protests, Jeremy informed Damon that she was on board with the plan.

Damon greeted Elena with a grin.

Damon’s discussion with Silas revealed that Qetsiyah would also be attending the masquerade gala in a Cleopatra outfit she had recently purchased. Silas relied on Damon to dispose of Stefan. Elena and Damon went to a masquerade party costumed as Anne Boleyn and Henry VIII, respectively. Damon suggested a waltz, but Elena wasn’t in the mood. She claimed that the death of Bonnie was not her responsibility, but that it was her own doing because she failed to realise the truth sooner. Neither is she going to let Megan’s murder go unnoticed. Qetsiyah apologised to Stefan by buying him a drink, which he accepted graciously. Damon said, “It’ll take a barrel,” and he and Stefan left the room. Stefan criticised Damon’s performance as a support man, and Damon replied, “Believe me, the last person to advance on her is still suffering for it.” Then Silas arrived. A simple “hello” from me. Damon slit Stefan’s throat. After Stefan’s “death,” the tether between them is severed, and Silas’s telepathic abilities return to him. Silas’s plan was to pretend to be Stefan.

Stefan eventually woke up. Damon injected him with vervain, and after explaining that he was doing it to get Bonnie back for Elena, he snapped his neck again. Stefan manipulated Damon into snapping Silas’ neck when the latter complained of a pain. “How do you feel about it, bro?” Silas was located by Damon and Elena. That Silas is no longer an option, in Elena’s opinion, is a positive thing. Damon, however, had suspicions that this was not the case. They needed him to help them find Bonnie.

Damon

Damon and Elena were having a conversation in the living room of the Salvatore mansion, where a lifeless Silas lay on the sofa. The only explanation for why Silas would give up his life for Bonnie’s is if he is a sorceress. Having the remedy is the only means to join the witching profession. The visitor who came to knock on your door was none other than Katherine. Katherine had the impression she had been brought there to prove to her that she had once again managed to avoid mortality. They’ve at last succeeded at something. So, how did you feel? This was “fantastic,” Damon exclaimed. Eventually, she understood it. She pleaded Damon not to kill her as she knew Silas would need all of her blood. Damon bit her throat. He put Katherine’s head to Silas’ lips and said, “Goodbye.” When Silas reached for her, he touched her forehead. Katharine fell to the ground. Damon then apparently became aware of something. There was a flutter in her chest. She opened her eyes. Are we in Purgatory?” she questioned.

With Damon’s aid, Elena is able to

Damon and Elena are enjoying a tender moment together on the sofa when Silas bursts in to spoil it by discussing their plans for his murder in Treat with Care. With sarcasm, Silas offers to pinky swear that he will return Bonnie to Elena before he leaves this world for good. Now is the time when everyone searches for the centre. Silas hopes that death will bring him serenity. Silas, seeing Elena as his real affection, declines to bring her along because he would be forced to gaze at her all day. When Elena starts to get irritated, Silas fires a magical crossbow bolt at her thigh. Damon takes this news badly and rushes to provide assistance.

The Two Brothers: Damon and Silas

Damon, Silas, and Jeremy take a journey to New Jersey in quest of the anchor and wind up instead in an enormous warehouse full of trash. Tessa uses Elena as bargaining chip against Damon by luring her to the lodge. She threatens to murder Elena unless Damon kills Silas before nightfall. Damon informs Jeremy that he must murder Silas to save Elena, so the agreement is off and Bonnie isn’t coming back. Damon returns to the building and is immediately surrounded by Travelers, one of whom greets him in a tongue he doesn’t understand. In a nod to the witches of Mystic Falls, they manage to render his daytime band ineffective just as Damon is about to murder Silas and them both. Amara is staggering around the building, muttering to herself, “leave me alone.” Damon tracks her down. Damon and Jeremy are having a sorrow party because they couldn’t convince Bonnie to return. Still, they reveal the episode’s major surprise to Elena and present her to Amara via Damon.

After Silas loses interest in reuniting with Bonnie in Death and the Bride, Damon seeks Qetsiyah’s advice. He approaches Qetsiyah with a request for an incantation that will establish Bonnie as the new tether to the other world. She decides to assist them because if they make that change, Amara will perish but the Other Side will continue to exist, ensuring that she can spend the remainder of eternity with Silas. Damon cynically responds, “To do the ritual, she requires blood from all three doppelgangers, Elena, Katherine, and Amara.” “The blood of a Doppelgänger, you say? They’re like doppelgangers sprouting from every orifice.”

In their relationship, Damon and Amara

While the enchantment is in progress, Silas steps in to break it. When the lights go out, Silas and Qetsiyah begin battling, and Stefan, who only wants vengeance against Silas for what he has done to him, kidnaps Amara. When Damon enters, he questions Elena about where Amara could be. She instructs him to locate Stefan instead because he wasn’t thinking clearly. Even if Silas had locked him up, it was their responsibility to release him. Damon arrives just in time to see Amara collapse to the ground. So that Qetsiyah can finish the ritual, he does everything in his power to keep her living for a few more minutes. After all their efforts, they succeed when Qetsiyah finishes the incantation just in time and Bonnie takes over as the new anchor. Stefan tells Damon and Elena at the conclusion of the show that he hoped they would be the ones to locate him and free him from the safe.

When Elena invites Damon and Stefan to her celebration in Dead Man on Campus, she phones them both. Damon attempts to reason with Stefan, but the latter is in a panic due to flashbacks of his many near-drowning experiences. It’s clear to Damon that something is awry, but Stefan won’t inform him.

Tormenting Wes is Damon’s favourite pastime.

Damon chooses to consult Dr. Maxwell later on at Elena’s urging. Damon investigates Maxfield’s laboratory specimens. He promises Maxfield that if he speaks, he’ll cure him with vampire blood after injecting him with an illness. Damon is disgusted by the fact that Dr. Maxwell is turning children into vampires for scientific study. Damon injects Maxwell with yet another vial of an unknown pathogen; this time it’s rabies. Maxfield then reveals that he was attempting to breed a new type of vampire that survives not on human but rather on vampire blood. Because of Elena’s concern for Maxfield, Damon promises not to murder him after he informs her that Jesse feeds on vampires.

Damon, in the lab, cuts his wrist to cure Maxfield of the numerous illnesses he’s inoculated him with, but Jesse bursts in, demanding explanations. After noticing Damon’s injured wrist, he launches an assault. Since Damon is a much elder vampire than Jesse, he doesn’t have to worry about being outmatched in power. Jesse chases him down the corridor and gives him a good tackling outside. When Elena comes upon them, Jesse has already defeated Damon and is feeding on him. Damon informs her that Jesse has his neck and is about to tear off his skull. When Caroline comes to investigate, Elena has already grabbed a piece of the door and stabbed Jesse to death with it. Damon informs Caroline that Elena had no option and then departs to deal with Maxfield, leaving Elena feeling terrible.

Abducted Damon

Damon does the dishes while Maxfield discreetly unties his hands and feet in the lab. It is Damon’s intention to force the entire incident out of Maxfield’s mind. The number on the blood container in the freezer jolts his recollection. Damon still recalls his own trial number from the 1950s. Maxfield has come to the conclusion that Damon was also a vampire of Augustine’s. Damon is indifferent as Maxfield escapes and dashes to the other side of the laboratory. Maxfield presses the “emergency protocols” switch, and the room fills with atomized vervain, knocking Damon to the floor. Damon awakens in an eerily familiar cage. The sight of his letters carved into the wall brings back horrific flashbacks of his time spent captive and tormented.

Captured Elena and Damon.

Damon awakens up in a cage in The Cell, where Wes Maxfield is administering a vervain injection. He explains to Damon that since he murdered their test subject (Jesse) last night, Damon will now serve as the new one. After successfully conditioning Jesse to develop a taste for vampire blood, Maxfield informs Damon that he is prepared to advance his investigation to a new level. Wes later locks up Damon and Elena in the same cage. When she comes to, Damon informs her that he’s been there before and that Whitmore tortured his victims by hacking them up into small parts every day. Approximately five years passed while he was there. When he was serving in Europe during World War II, he met Enzo, a fellow vampire who was serving in the military. Elena reveals to Damon that her father was an Augustinian who worked for Whitmore. She sobs because she can’t accept that he’s associated with the kind of people who would go so far as to sever Damon’s eyeballs. Damon approaches her, telling her he will rescue her.

Damon informs Elena that Enzo’s relationship is what allowed him to keep his humanity and keep living his previous life. The strangest part, though, is that he admits he never informed anyone, including Stefan, what occurred during his Augustinian incarceration. This means that if Stefan ever sees that they’re gone, he won’t know where to search. Damon describes his evasion tactics. Every year on December 31st, for Augustine’s New Year’s Eve celebration, the vampires are released for public display. Vervain and confinement had drained their strength. The curative abilities of vampire blood are demonstrated by Whitmore with the help of a willing participant, Mrs. Fell. When he slashes her hand, she consumes vampire blood to make it better. Enzo devises a scheme wherein one of them consumes both of their daily blood supplies for an entire year so that when they are released on New Year’s Eve the following year, one of them will be physically capable of fighting. Damon triumphs in a game of rock, paper, scissors with the gang. For his part, Damon isn’t telling Elena much beyond the fact that “it wasn’t beautiful,” but Elena is insistent on knowing the full story. He finally tells Elena because she assures him she loves him and doesn’t care what he did to get away. Damon confesses to Elena his greatest sin: he abandoned Enzo in the forest during his flight. After he wrecked the New Year’s Eve celebration by toppling over a candelabra, he attempted to liberate Enzo by smashing the cage, but the bars were vervained. Damon turned off his compassion for Enzo and abandoned him to burn in the following inferno. Elena was shocked when Damon abandoned her and Enzo.

Damon takes an arrow from Aaron’s gun.

Aaron carries his pistol to the subterranean rooms. He blames Elena for the deaths of Megan and potentially his parents. Damon interrupts and claims responsibility. Damon reveals that following Enzo’s death, he was left with no choice but to exact his vengeance on his own. He had intended to wipe out the Whitmores in one generation, save for one, raise him and his family, and then wipe out all but that family. Elena, repulsed, demands to know when the last one occurred. Sarah visited Charleston, South Carolina, not too long ago. In other words, it was a weekend getaway. After thinking about it, Elena remembers that they were dating back then. Damon is shot by Aaron, and Elena is devastated. After waking up, Damon discovers that Elena has been kidnapped by Wes and goes to check on her from her confinement.

Damon uses his last bit of power to make a hole in the stone wall in Fifty Shades of Grayson. Through the opening he reaches for the cartridge Aaron had dropped. Damon uses the cartridge to unlock the door after he has tried to access it by pounding on the latch with the boulder and kicking it.

The Slayer, and Damon

Damon comes to see Stefan and informs him they need to go get Elena, but he has no idea where she is, so they need pressure. If Damon and Stefan can’t get Elena back, then Wes gets to attempt to reconnect Aaron’s limbs and Damon instructs Aaron to contact his uncle. When Aaron arranges to meet Wes, they do so in Wes’s classroom. In Wes’s classroom, the Salvatores and Aaron discover Enzo already waiting for them. Damon attempts to rush through the small talk, but Enzo is anxious to tell him about the time he was left for dead in a fire and how he miraculously escaped. He says one of the researchers decided to spare his life. Even though Damon is eager to finally murder Aaron, the latter brings up the fact that he still has some papers Wes gave him hidden away in his bedroom. Damon is instructed to remain with Enzo while Stefan follows Wes.

Once again, Damon ignores Enzo’s guilt excursions while in class. Wes poisoned him, Enzo says, and he needs to come back for the cure. To save both Enzo and Elena, Damon proposes they join forces. As an alternative, Enzo fills him in on the fact that Wes forbade his return until Damon was no longer alive. After that, Enzo tosses him out of the window. Damon avoids a confrontation with Enzo, who continues attempting to pursue him. The toxin has weakened Enzo so much that he can no longer mount a serious assault. Damon presses him for information, but Enzo dries up before he can tell him where Elena is. To his surprise, Enzo finds himself in a laboratory. Damon explains to him that he gave him an injection of every known remedy. Damon puts his hand on Enzo’s heart and explains that in order to abandon him, he had to turn off his humanity. Damon was the most important person in Enzo’s life, but Enzo says Damon destroyed him and that Damon will always be a psychopath.

Damon returns to the Salvatore home later to find Elena immersed in her father’s diary. Megan had been mentioned in her father’s diary, which she discovered. Megan had a photo of Grayson Gilbert in her phone because he fixed her genetic heart problem. Damon isn’t shocked by Elena’s ability to find solace in the midst of unimaginable pain. When he thinks about all the awful things he’s done, he can’t fathom how Elena can keep forgiving him. She insists that she adores and embraces him because he is the one she picked. Damon says that he has made his decision and that he will let her go. After learning that he was tormented for five years, Elena begs him not to run away, saying that she, too, has done terrible things and that she will not condemn him. The two of them are arguing, and he yells at her to cease supporting him. Damon admits he is trapped in his nature but leaves Elena unchanged. Inconsolable, Elena breaks down into sobs.

Damon raises a glass to the inevitable demise of Katherine.

Damon has a hard time getting over his breakup in 500 Years of Solitude. Damon is inebriated and sad when Jeremy and Matt come across him at the Restaurant. Both of them can’t believe that Damon would abandon Elena like that. Damon pours shooters for Matt and Jeremy in the lodging house later on, to make up for everything Katherine has done to them over the years. Guests Elena, Caroline, and Bonnie enter and enjoy the toasting fun. Stefan rushes down to tell them they shouldn’t be so callous, but Damon cautions him not to let the fact that she looks like Elena detract from the fact that she’s a cunning sociopath. Her seduction of Damon and Stefan turned them into vampires and sparked a battle with the locals, which ultimately led to their deaths. However, he continues by saying that he will raise a glass to the fact that she went from being a scared girl who was rejected by her family to a courageous woman who managed to pull through. Damon pokes fun at Stefan for being so gentle with her after just one night of desire. Nadia then interrupts, saying she has figured out how to save her mom and she wants to tell her. Damon prohibits anyone from helping, so Nadia interred Matt in the safe on the property without his band.

Both Damon and Katherine

Damon plans to torture Katherine by manipulating her consciousness while waiting for Elena and Stefan to rescue her in return for Matt. Damon grabs a cushion and prepares to suffocate an incapacitated Katherine. However, Liz Forbes enters and puts a halt to that. “I blame her for all my bad behaviour. She showed me that killing could be fun and gave me the skills to do it. She destroyed my life, and there’s no way to get it back “he explains “Just look at how she’s able to keep you in check, Damon. Disprove her, “”Liz states” Damon plays with Katherine some more, but Nadia snaps his throat to halt him. Damon awakens on the floor, but he doesn’t move as Katherine explains to Nadia that she’s been greedy her whole life but now she wants to do the right thing for once. Nadia, she begs, please release me. Damon is taken aback by Katherine’s generosity.

As Damon and Stefan

After Stefan bids farewell to Katherine, he and Damon reflect on the events of the past few days. Damon now knows why Stefan treated Katherine so kindly. She was instrumental in getting Stefan out of his funk. Stefan orders him to resolve his issues with Elena. Damon agrees with Stefan that Elena is the greatest thing to happen to him in his life and admits that he can’t imagine his life without her. However, Damon believes that he is no better than Katherine and that Elena would be better off without him. He’s making an effort to be unselfish. A glance from Stefan is all it takes to persuade him to go after her again. Damon quips that Stefan should recall he was the one who persuaded him out of doing the right thing for all humanity when Damon gets Elena back and the world flips out for keeping the doppelgängers apart.

After a while, everyone congregates around the fireplace to drink whisky. Jeremy picks up on Alaric’s voice. “Where have you been hiding out? I thought you ditched us to go find some inner calm “So says Jeremy. Do you really believe I’d leave Damon in control and never turn back?” Alaric retorts. That you’re a jerk, according to Alaric, Jeremy communicates to Damon through Jeremy. Damon’s mood brightens upon seeing Rick, and the two raise a glass in his honour.

Damon is in the billiard room.

Damon has hidden Katherine’s corpse and refuses to reveal its location to Stefan in The Demon Within. Nadia is also present, having informed the Salvatore siblings of her desire to possess her mother’s body. The situation is hopeless, Damon informs her. Nadia becomes enraged and demands that Damon hand it over to her, but he swiftly declines. While Damon grills, Stefan tries to convince him to let Nadia have Katherine’s body. As they speak, Stefan is giving him encouragement regarding Elena. Soon after Caroline’s arrival, Damon begins confronting her about her animosity towards him.

Damon

At the Salvatore estate, Enzo is ready and waiting for Damon with a large corpse bag. Aaron, who is still living, is inside. He looked into Damon’s vengeance plan and concluded that the latter would want to see it through to a successful conclusion. Damon wants to make amends and win Elena back, so he kills Enzo before Aaron wakes up. I was caught off guard by that,” Aaron says. Damon takes Aaron’s vervain watch and forces him to flee town quickly. He then leaves for the celebration. Elena arrives at the gathering and immediately collapses into Damon’s arms, but Mia finishes the ritual and, in the midst of their reassuring embrace, Elena forever changes into Katherine.
Elena embraces Damon.

Damon gives an emotional plea for them to reconcile, explaining that he made a mistake in believing he could change her and that she made a mistake in thinking she couldn’t change him. Katharine will have nothing to do with it. “I’m happy to hear that I help you become a better person, but that’s a lot of weight on my shoulders. You can’t have nothing else to focus on but me.” When Katherine/Elena leaves, Damon is devastated.

Damon has succeeded in getting Aaron to leave town. An unconscious guy in the road prompts him to pull over, and he assists the man. Enzo is the guy who stands up. Damon suddenly materialises behind Aaron and explains that the reason he’s there is Elena. “That I am a demon is in her mind. Absolutely, she is correct.” After that, he gorges himself viciously on Aaron’s blood.

Damon and Enzo are shooting pool.

When Damon needs a break from thinking about Elena, he plays billiards with Enzo. After hearing about Damon and Elena, Enzo attempts to get a feel for the situation. Damon flips the tables on Enzo by inquiring about his lost gf Maggie, whom the Travelers were meant to assist him locate prior to their suicide attempt. Then, Caroline calls and tells him about the strange dreams Stefan and Elena have been having about one another. He has requested that she visit his home with a sorceress. Damon and Elena have an uncomfortable post-breakup meeting when Caroline and Elena show up at the home. From another room, Caroline and Enzo listen in on their discussion. They make an effort to behave like any other couple, but Elena’s suggestion that they become pals causes Damon to recoil in horror. The conversation then shifts to Damon’s images of Stefan. Liv’s sibling Luke, who is also a sorceress, soon interrupts them.

Luke explains that Markos, the head of the Travelers, has returned from the afterlife. He says that Stefan and Elena are being drawn to the Travelers through their dreams, but that they need more information. Damon drinks outside later that night, “listening to the cosmos chuckle at me,” he informs Elena. “There was no hope for us, Elena. This is where we were destined to be.” She reassures him that he is not dreaming and that the world has no power over anything. Her second glimpse shows her the home’s location, so she tells everyone where to locate Markos. Damon and Enzo track down Markos, who reveals that the doppelgänger prophesy is false and that the only reason doppelgängers are attracted to one another is because of an enchantment he performed 1500 years ago, when Travelers required their blood.

Damon, Enzo, and Markos all get together.

In the middle of their stroll, Markos tells Damon that the Travelers’ history begins with the creation of the longevity magic by Silas and Qetsiyah, which led to a rift in the community and the emergence of the witches who sought to keep the Travelers divided because they are stronger as a whole. The magicians’ spell prevented the group from permanently establishing itself in one location. It can be fixed by doppelganger blood. He assures Damon that they don’t mean any harm and promises to put a stop to the dreams. Damon then sees a group of travellers who have taken hosts in Mystic Falls citizens emerging from the crowd. The images end when all the Travelers cast the magic at the same time.

There is no way Damon can be Elena’s buddy.

Upon his return, Damon discovers Elena waiting for him in his chamber. She reassures him that their relationship is genuine, despite the fact that it is chaotic and complex, and that the images were just a fiction. Damon counters that they are still a poor match. When Elena insists that she needs him in her life despite their differences, Damon gets defensive and says they can’t be pals anymore. After a brief struggle, Elena manages to exit the room without breaking down.

Damon is preoccupied with the predicament with the Strangers in Man on Fire. He visits Matt and Jeremy at Tyler’s home in an attempt to steal the Traveler knife, but they can’t seem to locate it and haven’t heard from Tyler in quite some time. In a fit of rage, Damon phones Enzo and begs him to join him on a hunt for the Travelers, but Enzo declines, saying he has other commitments. Later, though, he contacts Damon and has him look into Stefan’s diaries beginning on November 8, 1960. Damon informs him that Stefan torched the entire lot. Then, Enzo discloses his plan to exact vengeance on Stefan and Elena by accusing them of murdering his one true love, Maggie. Damon talks to Caroline’s mom about Maggie’s passing and leaves a note for Caroline. After reviewing the crime scene pictures, Damon realises he has seen it before. “Truthfully, Stefan was correct; he was not the one who murdered Enzo’s girlfriend. I did, “This is what Damon reveals to Liz.

When Enzo begins to disconnect from his humanity, Damon attempts to halt him.

He rushes to Whitmore and discovers Enzo with Stefan and Elena shackled with vervain cords. On November 8, 1960, he tells them, a lady left a note at his home saying she wanted to question him. The fact that she was actually Enzo’s Maggie went completely over his head. In her quest for vengeance, she had no hope of defeating Damon. Damon had murdered her and framed Stefan for the crime out of resentment at Stefan for abandoning him during the five years he was held captive by Augustine. Damon tells Enzo that they need to work things out between themselves and not involve anyone else. Enzo admits he doesn’t want to detest Damon because then he’d have nothing left to live for. After considering his options, he decides to disconnect from mankind.

Elena receives assistance from Damon.

No decency At the moment, Enzo is feeling very upbeat. Damon recommends that Enzo come along with him, and he gives Stefan a piece of glass to break free. Enzo bites Liv and uses the shattered glass to strike Damon in the neck. When Stefan finally manages to extricate himself, he tries to drag Enzo off, but Enzo quickly escapes, grabbing Elena and running off. While Damon pursues Elena, Stefan remains behind to give blood to Liv, who has been gravely injured. In his communication to Enzo, he begs him to spare Elena’s life. He comes across Elena passed out outside of Whitmore College and brings her to her apartment. She falls to the bed, where he gently touches her face. Her consciousness begins to return just as he vampiricly escapes.

Enzo, Damon, and Stefanie

Damon promises Stefan that he will locate Enzo and make everything right when they return to the Salvatore home later. Stefan denies any responsibility for Enzo’s death and insists that he is unaware that his friend is deceased. Damon says Enzo kept him grounded in his sanity during his imprisonment by constantly telling him of how fortunate he was to have any family at all. Damon owes Enzo because Enzo persuaded him not to lose confidence in his sibling every time Damon was ready to give up on Stefan. The siblings have a drink while Enzo’s spirit looks on. “Damon, it’s too late to apologise now. You know I’m the type to hold on to a grudge forever. This is only the beginning of it, “And Enzo says.

Damon asks Luke for assistance in What Lies Beneath when he can’t locate a trace of Enzo on his own. Damon assures Stefan that locating a vampire who has turned the humanity switch and now desires his death is worthwhile, but Stefan counters that Enzo would rather not be located because he is under the influence of a concealing enchantment. Tyler enters and reports the weekly issue. After discussing the situation, they have decided that Stefan and Elena will likely be visited by the Travelers today in order to free them from the witches’ spell and allow them to permanently reside in Mystic Falls. Damon orders Tyler to talk to the Traveler inside of him in order to find Markos, tells Luke to cast an anti-locator spell in order to keep the Travelers from finding Stefan and Elena’s doppelgangers, and tells Stefan that he and Elena’s other doppelganger will be taking a trip together in order to keep them both safe.

Damon and Elena

In order to avoid the Travelers, Damon, Stefan, Elena, and Caroline resolve to take refuge in Caroline’s father’s secluded cottage. They bring Luke along so he can cast an anti-locator charm and keep them hidden from the strangers. Damon drops by while Elena is unloading to chat about the lodge and Caroline’s dad. Elena then questions Damon if he is still interested in ignoring her because he has mentioned it. The Reply of Damon “Sure. No. I can’t say.” Damon questions Elena if she is evicting him after she provides him an escape. Taking up where he left off, she says “Yeah. No. Really, I have no idea.” They grin at each other flirtatiously, but the discussion quickly becomes uncomfortable after Damon brings up Enzo. Having lied to Damon about Enzo’s murder at Stefan’s hands, Elena feels terrible remorse and leaves an explanation.

Damon, Elena, Caroline, and Stefan are having fun.

Caroline creates charades hints while Damon mixes drinks. The topic is “secrets people believe they’re getting away with,” and she’s confident that “Team Stelena” can handle it. He recognises her “judgmental little hinty intonation.” In her opinion, they are being covert. Caroline believes it has more to do with the two of them than Damon does, who thinks she became evasive when he mentioned Enzo. As night falls, the group is still acting normally, with no hint of a secret in sight. Damon then recommends playing “Never have I ever” Caroline finally breaks the ice by declaring, “Never have I ever kissed a Salvatore sibling — today.” Damon continues, “I have never misled about where Enzo is.” The evening comes to an abrupt end as Stefan and Elena fall quiet. As soon as Elena finishes her dinner, she heads straight for bed.

Elena is saved by Damon.

Enzo’s spirit, who can now contact physical objects, attempts to smother Elena while she’s in the tub as an act of vengeance. Once she’s breathing again, she calls out for Damon. He rushes over to help her and uses a cloth to cover her up. As Elena freaks out, he attempts to reassure her. Damon then contemplates the afterlife and its baffling desire to harm Elena. The truth about Enzo’s murder is finally out, she says. Damon joins Stefan and Caroline, and they realise that Enzo’s plan to murder them all was just a diversion involving Elena’s death. The Travelers can now follow them because he took Luke somewhere they can be found.

As Damon and Stefan

When Damon finds out that Enzo is deceased, he turns to Stefan and asks what he plans to do. Kill me, Stefan yells. They hear a voice from the garage and discover a scarcely living Luke before Damon can respond. Damon casts the incantation on the gas, and then Enzo pulls the plug on a lighter to fire it. When the fire starts, it spreads rapidly through the house. By assaulting them, Enzo gets to corner Stefan and Damon in the garage. Damon convinces Enzo to let go of his vengeance by pledging to bring him back, so he begs Stefan to flee with Luke. After that, Damon bolts out of the outbuilding. After returning to the Forbes house, Stefan begins to repent to Damon but is cut short by a strike from the latter. “I felt responsible to act in this manner for Enzo’s sake. However, I promise this is the final time we’ll ever talk about it “This is what Damon has to say.

In this scene, Damon leans in for a passionate embrace on Elena.

Damon packs up the vehicle later on in preparation for a relocation, and Elena comes up to talk to him about it. He brushes her off and urges her to move quickly, saying that the Travelers must be approaching. She expresses regret for concealing Enzo’s demise, but he insists he doesn’t give a damn about her fabrications. Since she doesn’t understand his behaviour, she confronts him about it. The man then reveals that he knew she had misled because she was scared that he would lose control again, but that he was able to resist the urge this time out of love for her. Elena queries, half-jokingly, if he is still angry with her. And then he adds to her perplexity by saying, “Of course I’m still angry at you because being around you drives me crazy, and not being around you drives me insane.” Damon rushes up to her after staring at her for a while and gives her an intense kiss. Elena asks in a hushed voice, “What was that for?” and he replies that he needed it because he had a really terrible day. He enters the house, leaving Elena to bask in the light for a moment before the Travelers appear and Markos snatches her away from her.

Damon puts the Wanderer through hell.

Damon has been looking frantically for Stefan and Elena for the past four days in Promised Land, since they were abducted by adventurers. Within the body of Sykes, he is cruelly tormenting a Traveler. After explaining that the Travelers need to undo the witch’s enchantment in order to calm down, he inquires as to where Markos is. Damon manages to ungag the Traveler long enough for him to tell them that they can do nothing to halt Markos. He receives a call from Stefan later on, who tells him that he and Elena have escaped the Travelers but are currently at a loss as to their whereabouts. Damon teases that Elena will kill Stefan in the eyes after he hears that Stefan has Elena out shooting rodents with him. Damon promises to track down and execute Markos and also requests that he and Elena get back home unharmed.

Damon takes over the bodies of the Travelers.

The spirit of Enzo reminds Damon, after he hangs up the phone, by stabbing him in the breast with a dagger. Damon reminds Bonnie that he has to deal with Markos, so he recommends that she ask Liv to include Enzo in her enchantment to prevent the Other Side from collapsing and save Bonnie. Damon and Jeremy depart to retrieve the actual corpses of the Travelers, which are hidden within the caverns, before Bonnie can inform her there is no such thing. Once he, Matt, and Jeremy brought back the Travelers’ comatose corpses, they began strewing them about the boarding house. Damon’s disdain for Tyler, who is bound in the cellar, prompts Caroline to charge him of being petty because of Elena. Until she finds a way to save Tyler, Caroline begs him not to oppose the guest within Tyler.

Markos and Damon get into a brawl.

Markos chooses to pay Damon a call at the lodging house after he discovers a letter from the latter in the caverns, instructing him to get in touch about the missing witch want tobes, aka the Travelers. Markos, back at the home, doesn’t seem worried about his folks. To make his point, he stabs one in the neck and tells Damon he doesn’t care if they ever regain control of their bodies. He says that Travelers can be found anywhere and everywhere, and that they are ready to sacrifice their lives for a chance at a better future. Markos adds that only Nomad magic will be left after they cast the ritual and its effects spread from Mystic Falls. Julian, hiding in the cellar while they speak, tells Damon that Markos has no idea he’s there and that he should take advantage of the situation. Damon uses an alibi to sneak downstairs and give Julian the key to the basement.

Injured Damon.

Julian launches an assault against Markos, but it’s too late; the Travelers have already begun casting their ritual, which causes Julian’s canines to vanish and Damon’s ring to become ineffective. As the witch casts her incantation, the Travelers inside the Salvatore home begin to reawaken. Suddenly, Damon receives the same type of gunshot wound to the torso that he did when he perished as a human. Markos says that because the enchantment will break down spirit magic, vampires will keep dying the way they were meant to when they were humans. Damon and Julian begin their escape from Mystic Falls by frantically rushing towards the exit. Damon, who has lived in his house for over a century, gets one last, heartbreaking glance at his neighbourhood before he moves away. Finally reaching the road, Damon calls for Jeremy to fetch him up.

In order to avoid the Travelers’ curse, Elena, Damon, Stefan, Bonnie, and Caroline have made plans to gather in Whitmore and then embark on a long journey. Elena meets Damon at the Whitmore station and gives him an intense kiss. She quotes his words from their last kiss: “I had a really bad day and I needed it” when he inquires as to why. Additionally, she says she feared she would never see him again and that she feared dying a horrible death. As they bask in their moment of pleasure, Stefan announces that he will be waiting for Caroline and Bonnie. After saying their goodbyes to Jeremy, Damon and Elena get into the vehicle and drive away.

Damon is gearing up for operation Kaboom.

Damon and Elena learn of Stefan’s passing from Caroline in the comfort of their own home. Damon is confident that Bonnie and Enzo will return because he knows that Bonnie has a plan to bring them back. Upon hearing Bonnie’s news that the Traveler who knew the spell to bring people back from the other side has been sucked into darkness, Damon sobs uncontrollably. As the reality of losing Stefan for good hits him, he begins to throw things. He even threatens Bonnie to do something. Enzo interrupts them and reveals he has found another Traveler. Damon then meets Matt and Jeremy at Whitmore to plan their Travelers massacre. Killing them all will overwhelm the anchor and with the help of a spell they will be able to bring people back from the other side.

Later, Damon tells Elena that Matt and Jeremy are going to blow up the Grill and then he tells her that someone has to set off the explosion. Elena says no and asks if he sees a future with her. He says it’s all he has seen since the moment he met her. She asks why then would he go on a suicide mission and he says it’s only half of one because if he dies, he will be brought back with the others. He tells her it’s his choice and she has to respect it. He promises her that he will make it back to her. Elena looks at him for a moment and then kisses him passionately. When they pull apart Damon says it again “I promise.”

Damon about to sacrifice his life.

While waiting for the signal from Liz, Damon sits outside of the Town’s city line and drinks a bottle of alcohol. When he gets the confirmation from Liz that the plan is on go, he sits in the driver’s seat of his car and proceeds to drive into town, but Elena gets in the passenger seat besides him. Elena says, “You said to respect your choice. Now you can respect mine.” Damon looks somewhat shocked that Elena would be willing to die with him so that they’re together rather than let Damon die alone. Seconds later the car ploughs through the Mystic Grill filled with the Travelers, Damon and Elena give each other one last longing look. Elena is about to tell Damon that she loves him but he tells her he knows. They both die ending up on the Other Side.

Bonnie reveals to Elena that Damon can’t be brought back.

Elena and Damon find Bonnie. She tells them to pass through her, find their bodies on the Other Side and come back quickly. They both nod and pass through Bonnie. Damon wakes up on the Other Side but sees Liz on the ground. He tries to help her but struggles. Alaric finds him and together they rescue Liz. He then says “Friendly advice, when you get the girl, don’t blow her up.” Damon laughs and says “Good to see you too, buddy.” Later they both go to Bonnie to pass through her and return to the land of living. Alaric goes through Bonnie and Damon pauses to find out where Elena is. Bonnie assures him that she has returned and then Damon tries to pass through her but nothing happens. They realise that Liv who was performing the spell to bring them back has stopped it making Damon unable to return.

It is time for Damon to say goodbye to Elena. He finds her crying hysterically in the crypt and she says “You lied to me”. A ghost Damon says “Even if I wanted to apologise, you couldn’t hear me, so I won’t.” He strokes her face and she appears to feel his touch but can’t see his hand. Damon then says to Elena, “You are by far the greatest thing that has ever happened to me… The fact that I got to die knowing I was loved… is the epitome of a fulfilled life… It is never going to get better than this. I peaked.” Elena distraught with grief makes one small plea to Damon, “Please, please come back to me.” Damon then says goodbye and disappears.

Bonnie and Damon’s fates are left unknown.

Later, Damon finds Bonnie and the ground begins to shake underneath them. “This place is going down isn’t it?” Damon says. She knows there are a thousand other people they’d both rather be with, but they take each other’s hand as the light gets brighter and they wait for whatever is coming. “Think it’ll hurt?” Bonnie asks. “I don’t know-” Damon says, and then he’s cut off by the bright white light. The fates of Damon and Bonnie are left unknown at the end of the episode.