Damon and Elena, better known as Delena, formed the beating heart of . They had a truly epic romance, but Elena was not the only love interest that Damon Salvatore had. Charming, witty and devastatingly handsome, Damon had many romances throughout the show. Some of them were serious relationships, while others were just flings that didn't last long.
While Damon was capable of sincere affection, not all his lady loves experienced this with him. Before his villain redemption arc, Damon compelled and used people when he felt like it.
His affairs can be ranked definitively based on the quality of his relationships, how he treated his significant other and how he evolved personally at that stage in his life.
Season 8's Siren, Sybil was , mainly because of how she wormed her way into Damon's life. She had used her Siren song to make Damon harvest souls for her to feed on and send to hell, but she went deeper into his subconscious. Sybil started replacing memories of Elena and Bonnie in Damon's mind with herself so that he would stay in her control and keep doing her bidding.
Damon did manage to break free of her influence a number of times, notably when Sybil showed him Elena's necklace and even dressed like her at the Miss Mystic pageant, but she manipulated him in too many ways during other instances. The "love" or even companionship between Sybil and Damon was a product of her supernatural powers, and she transformed Damon into the worst version of himself deliberately.
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Before Caroline became a vampire and came of age, she was targeted by Damon because he saw her vulnerability. Rejected by Stefan, she saw her relationship with Damon as a victory over Elena, but in truth, Damon had been compelling and feeding on her for his own selfish needs. When he felt like she had outlived her needs, he wanted to kill her.
There was no way to cushion the blow, but Damon had used Caroline indiscriminately and dumped her when he wanted. Damon was also never held accountable for his actions, which made his future friendly relationship with Caroline even worse.
Damon had a penchant for compelling women and starting romantic relationships with them. This does not sit well with audiences to date, and they feel that . After Rose's death, Damon met Andie, Jenna's friend, and used compulsion on her for sexual gratification and to use her as a blood bag.
Their relationship actually lasted pretty long, and it seemed as though Damon had developed feelings for her. Still, it did not make him change his ways, and keeping her so close to him led to Andie's death.
She had attempted to help him find Stefan, but Stefan killed her for it. Andie was a bright young woman with a future ahead of her, which was ruined by Damon's selfishness.
Rebekah shared a romantic history with Stefan, but Damon had an intense one-night stand with her in Season 3 after facing rejection from Elena. Rebekah, too, had been told off by Matt, and she found comfort in Damon for a night. When Sage told Damon to get more information from Rebekah about White Oak trees, he got intimate with Rebekah once more to make her reveal her secrets.
Later, when she found out about Damon's treachery, Rebekah made sure to make him pay. She tortured him for his betrayal since love and romance were sensitive topics for the Original sister. They had a bittersweet relationship after this, bordering on friendship and hatred, depending on the alliances they formed to get the cure.
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With couples like Klaus and Caroline and Stefan and Elena, The Vampire Diaries was full of passionate, charming, and romantic quotes that fans loved.
Like many of his relationships, Damon treated Lexi unfairly. She had helped Stefan control his bloodlust, and when Damon had his humanity off in the 1970s, Stefan asked Lexi to meet him and help him, too. Damon pretended to have turned off his humanity switch to Lexi, confessing that it was because he loved her deeply. Unfortunately, after a night of passion, Damon showed his true colors.
He took away Lexi's daylight ring and locked her on the terrace so that she burned when the sun came up.
Damon admitted that the guilt of his actions kept him up at night sometimes, but when Lexi rolled back into town, he trapped her and staked her in one of instead of asking for her forgiveness.
It could be said that Katherine Pierce was Damon's first love. She was also the woman who betrayed him in the worst ways and had little to no remorse for it. had met Damon when she came to live at the Salvatore Boarding House, and he quickly fell for her charming ways. At first, Damon did not know that Katherine was a vampire.
Later, when he did find out, he willingly consumed Katherine's blood because he truly loved her.
Katherine didn't care much for him, since she was also compelling and romancing Stefan at the same time. It was because of Katherine that Damon got turned into a vampire and that he had intense trust issues in his relationships. Damon spent years trying to get her out of the tomb, only to find out that it had all been a lie and that Katerina Petrova had never loved him.
Rose and Damon's relationship was a heartwarming one, where he finally showed his better, kinder side to fans as well as to Rose.
Rose came into their lives as an agent for the Originals, but she and Damon grew close when she switched sides and chose to help protect Elena.
They had a short but impassioned relationship, but Rose knew better than to be fully involved with a man who loved someone else. She was aware of Damon's affection for Elena, so they chose to be friends with benefits. She truly understood Damon, but their romance came to an end after Rose was bitten by a werewolf. He had to stake her to put her out of her misery, but it was obvious that he had grown to care for Rose in their brief time together. She brought out the very best in him.
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Delena was the most shipped couple in The Vampire Diaries. These episodes depicted Delena's first kiss, first dance, and much more.Elena Gilbert was The One for Damon, and even if it took a long time, she realized that he was her soulmate, too. Elena had first dated Stefan, which was why the situation became extremely complex when she started developing feelings for Stefan's brother, Damon. She denied the reality of a future with Damon for a long time, but even Elena couldn't control the electrifying chemistry between them.
For Elena, Damon wanted to become a better person. He mended his previous self-destructive ways to be good enough for her and admitted that he wanted to be human all along. After countless hurdles and years, when Elena was put under a spell in a coffin, they got the happy ending they deserved.
The lives, loves, dangers and disasters in the town, Mystic Falls, Virginia. Creatures of unspeakable horror lurk beneath this town as a teenage girl is suddenly torn between two vampire brothers.
