|“||Now this is what I've missed: two people connecting... It's lonely on the Other Side... and I swear being invisible will drive you mad. The way you couldn't see me standing in front of you, or feel my breath on your cheek as I whispered all the ways that I wished for you to suffer.||”|
Throughout The Vampire Diaries Series
In Dangerous Liaisons, Elena first saw Kol at the ball the Originals threw for the town when they were reunited but neither interacted directly; Elena being too busy with her meeting with Esther and Kol too involved with trying to kill Matt Donovan.
In Heart of Darkness, Damon and Elena went to Colorado to pick up Jeremy only to discover that Kol had beaten them there. He intercepted them at a batting cage where he attacked Damon. Later, when Elena and Damon went to Mary Porter's house to learn which Original started their bloodline, Kol again, was already a step ahead of them. He had killed Mary to keep the identity of their Original sire hidden and then continued his assault on them, beating Damon. When Elena tried to flee, Kol got in her way telling her that Klaus had said she was off limits but he would ignore that if need be. He pushed her down hard before finishing his beating of Damon and then departing, leaving Elena rattled.
In After School Special, when Rebekah had taken Elena hostage in the high school to learn more about the cure, she saw Kol arrive with Professor Shane in tow. Kol looked at Elena and just laughingly chastised his sister for being worse than Klaus.
In A View To A Kill, Elena had decided that the most efficient and safest way to grow Jeremy's Hunter's Mark would be for him to kill Kol. So she began her plan to bring him down, wanting to lure him into a trap where Bonnie would use her powers to hold him off while Jeremy dealt the killing blow. She called Kol up, requesting a meeting but Kol wanted it to be on his terms, arriving at her front door seconds later. He told her that the only way they would be speaking would be if she invited him in but Elena was cautious, telling him that she'd only let him in if he let Jeremy go. He agreed and was invited inside but not before Elena had noticed the White Oak Stake in the inside of his jacket.
Kol and Elena spoke casually, Kol going so far as to play a video game Jeremy had been playing minutes earlier. Elena began trying to fix them drinks, questioning what Kol had done wrong to deserve being daggered a century ago. Kol took offense, saying he didn't do anything and it was simply his brother's cruelty that made him wind up in a coffin for one hundred years. Elena then brought up Silas and Kol explained who the immortal was and what would happen if he was awakened. When Elena asked why he believed so much in Silas, Kol described how he used to hang out with witches and that they also feared Silas, and though Elena tried to keep stalling for time for Jeremy to come back with Bonnie, Kol left, leaving an omen that some things are better left buried.
When Jeremy got back home, Kol returned, telling them he'd thought about Elena's truce offer but had decided against it. Elena and Jeremy ran into the house but Kol pursued. They did their best to fight back with stakes and wooden bullets but he kept on coming, impaling Elena with a piece of the wooden staircase in their house. It took a few minutes but Elena pulled the wood from her gut, managing to save her brother using full speed just in time from Kol chopping off his limbs. She jabbed the Original's knife into his side, pressing him up against the counter while Jeremy sprayed him with vervain. This gave Elena enough time to get the white oak stake from Kol's jacket and give it to Jeremy who stabbed him with it. Elena watched as Kol went up in flames, screaming and tumbling through the house to his death, but not before Klaus had got there to bear witness to his younger brother's death, swearing vengeance on Elena.
In The Walking Dead, after Bonnie had temporarily brought down the veil to The Other Side , Kol crossed over to Mystic Falls, wanting to kill Elena for the part she played in his death. He found her at Jeremy's grave, telling her that The Other Side was isolating to the point of madness but in that isolation, was able to think of countless ways to make Elena suffer. He beat her down and strangled her until she begged for him to kill her to which he happily tried to oblige. However, Jeremy had also come from The Other Side and attacked Kol. The distraction gave Stefan the chance to snap Kol's neck and put a temporary end to Kol's rampage.
In Graduation, Kol had been trapped by Bonnie's magical barriers and when Elena went looking for Bonnie, she accidentally discovered Kol. Kol assaulted her, happy to be getting another chance at vengeance but before he could much harm, the veil to The Other Side was sealed, taking Kol along with it and saving Elena from his wrath.
- Curiously, Elena had Kol's phone number in her contact list even after his death.
- Kol: "Now this is what I've missed: two people connecting... It's lonely on the Other Side... and I swear being invisible will drive you mad. The way you couldn't see me standing in front of you, or feel my breath on your cheek as I whispered all the ways that I wished for you to suffer."
- [He grabs her by the throat and lifts her as she struggles to breathe.]
- Kol: "But alas - now you can."
- Elena: "Go ahead, Kol - kill me. You'd be doing me a favor."
- Kol: [whispering] "As you wish, darling."