After eight seasons of drama, tension, and even a sleeping curse, Damon and Elena finally get their happily ever after in the finale of The Vampire Diaries. Their love was messy and epic – and sometimes the love triangle made it seem totally impossible – but it was worth it to see them end the show together, happy and human.
Even though it wasn't until season four that the pair actually got together, episodes where Elena is still with Stefan are critical to their storyline. Any Delena-centric rewatch covers the key beats of their relationship – through the highs and the lows.
Damon and Elena don't get off to the best start. Stefan warns his new girlfriend of his brother from the day they first meet, and Elena is (rightfully) horrified by the way Damon treats Caroline.
However, this all changes in "Bloodlines". After saving Elena from a car wreck, Damon takes Elena along on a road trip to Georgia where they bond in the bar and first start to get to know each other for real. It's very much a friendship at this point, but this was the turning point for the two, marking the first time Elena really starts to like Damon's personality.
With the exception of one flashback scene, Damon and Elena spend the entirety of "The Departed" apart. Rushed out of town by Matt, Elena is finally forced to choose between Damon and Stefan. She ultimately chooses the latter, but is forced off Wickery Bridge and killed before they reunite.
It doesn't sound like a recipe for a Delena episode, but the setup makes it critical. Elena notes that she may have made a different choice if she'd met Damon first, only for a flashback to reveal that they did and Damon compelled her to forget. For fans eagerly waiting for the pair to unite, this was the first real sign they might actually be endgame.
Season three opens with Damon and Elena in the midst of their summer-long search for Stefan after he left town with Klaus. This doesn't sound like a recipe for romantic development, but this intense period of time alone together has changed them. Their bond is tighter, and Damon is suddenly one of the people Elena trusts most.
This episode is full of strong scenes, like when Damon returns Elena's necklace as a birthday gift. But it's the retrospective meaning that makes it such a pivotal episode. Later, in season six, Elena reveals that this was the moment she realized she loves Damon, adding a new layer of tension to the rest of the episodes before they eventually get together.
Damon and Elena's tentative friendship seemed to come to an end when Damon, drunk and upset by Elena's rejection, snaps her brother's neck. This is usually a point of no return, but Jeremy is wearing his Gilbert ring and comes back to life – and, slowly, the two repair their friendship.
By the time the season two finale rolls around, Elena cares for Damon just as much – if not more – than she did before. With him seemingly dying of a werewolf bite, she kisses him for the first time. It's more of a goodbye kiss than anything else, but the episode confirms that despite her protests otherwise, she does have romantic feelings for her boyfriend's brother.
The tension between Damon and Elena is palpable throughout most of season three. With Stefan out of the picture for the most part, Elena struggles to fight her growing attraction to Damon – before finally giving in during "Heart of Darkness".
While on a road trip to find Jeremy and contact Rose on the Other Side, Elena learns what Damon did for Rose in her final days. Overwhelmed, she initiates their first make-out session in the middle of a motel hallway. This was the culmination of years of tension, making this one of the show's most anticipated episodes (and one of the best kisses in all of The Vampire Diaries).
Elena and Damon are just becoming real friends when Stefan goes off the rails in season one. His timing isn't great; it's the Miss Mystic Falls pageant, and his pursuit of bloodlust leaves Elena alone and at risk of humiliation in front of the entire crowd.
Thankfully, Damon steps in and takes Stefan's spot for the dance. It's a first in many ways: Damon's first real romantic gesture, the first obvious display of his and Elena's powerful chemistry, and, as Elena reveals to Alaric in season 6, the first time she finds Damon attractive. More than anything, this episode highlights the difference between him and Stefan – and why Damon is better suited for Elena.
She's had plenty of experience with death by this point in the show, but Elena refuses to process Damon's loss. Instead, she asks Alaric to remove all memories of their relationship – only for Damon to return to Mystic Falls, alive and well after escaping Kai's prison world.
Desperate to remind her of what they've lost, Damon tries to help Elena remember key moments from their time together. It's heart-wrenching to watch – especially considering how long it took them to get together the first time – but also delivers one of their most romantic scenes, when he thinks back to the time he promised her forever and kissed her in the rain.
Even though Damon's emotions for Elena were clear long before "Rose", this is the first episode where it's completely laid out on the table. When Elena is kidnapped by Rose and Trevor, Damon joins Stefan to rescue her – and Stefan makes it very clear that he knows his brother is in love with his girlfriend.
Damon doesn't deny it, and later says those three little words to Elena for the first time before erasing the memory of his revelation. It's the first truly selfless thing Damon does in the show, and it's a turning point for the way he treats Elena moving forward.
Damon and Elena's relationship only gets more tumultuous once it's officially romantic. After the revelation of the sire bond and then Jeremy's death, it seems like there's no chance they'll ever get to be together for real.
But then there's "Graduation". With the sire bond now broken, Elena confirms that her love for Damon is true and chooses him over Stefan. It's one of the most satisfying Delena episodes, marking the end of The Vampire Diaries' love triangle trope once and for all, and it's the beginning of their official relationship.
The clock starts ticking on Stefan and Elena's relationship the moment she becomes a vampire. It finally comes to an end in season four's "We All Go a Little Mad Sometimes", with Damon and Elena kicking things into gear in the subsequent episode, "My Brother's Keeper".
Considering Elena cites Damon as the main reason for her breakup, this entire 40-minutes is filled with delicious tension. Finally, the timing is right for the pair to get together. Even with the revelation of the sire bond, it's a massive moment to see both totally give in to their emotions after repressing them for so long.
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