Neither participant could take their eyes off each other, evidencing their passionate connection. Elena continued to dance around her feelings for Damon in season 3. During their road trip to Denver in "Heart Of Darkness," the doppelganger finally gave in to passion and shared an intense make-out session with the elder Salvatore on a motel balcony.
Damon and Elena's chemistry continued to intensify as they searched for the originator of the Salvatores' bloodline. Their steamy lip-lock was an inevitability, though the road to their happily ever after remained rockier than ever.
Damon confessed his feelings to Elena for the first time during season 2's "Rose" after seeking her out to return her vervain necklace. Before remitting the jewelry, Damon admitted to being in love with his brother's girlfriend — before erasing all trace of his confession from her memory. Damon's declaration of love was immediately followed by one of his first selfless acts in the series.
The vampire recognized Elena's good heart and conceded that his brother was more deserving of her love. Elena broke the hearts of Delena fans everywhere during the season 3 finale when she finally made her choice between the Salvatore brothers.
She struggled with both, all season long. As she told Stefan in episode 18, "I never stopped loving you. Somehow, The Vampire Diaries managed to build a new love story without destroying the one that launched its series. And furthermore, it found a way to make Damon feel like a viable candidate, despite Elena's unfaltering love of Stefan, which meant viewers went into the season 3 finale genuinely not knowing which brother Elena would choose. After all, her options were very different.
McQueen in episode 19, "[Stefan's] love is pure; he'll always be good for her. Damon is either the best thing for her or the worst. Or the worst? It all built to the second half of the season finale, when Elena had to make a decision because she believed both brothers were hours away from dying.
She had to choose which one got the goodbye. And ultimately, she chose Stefan. Because, as she told Damon, "No matter what I feel for you, I never unfell for him," a line that acknowledged her feelings for both brothers and allowed viewers to understand her decision. And just to make sure the Delena shippers didn't lose hope, the writers threw in a flashback that revealed that Damon and Elena actually met first.
In its third season, TVD told a beautifully balanced, perfectly paced story about a human girl torn between two very different vampire brothers. And in the end, she made her choice. As she'd later claim, it was the best choice she ever made, and for viewers, it was one of the best love triangles TV had ever seen.
The Vampire Diaires. The two then share their first epic kiss soon to be many. Over the course of the series, fans are led to believe that Stefan is the first Salvatore whom Elena meets. Though the new vampire believes her unyielding feelings for Damon are genuine, Stefan and best pal Caroline Candice Accola discover that Elena is actually sired to him. The fourth season of the series is an emotional roller coaster for Elena. From breaking up with Stefan to being sired to Damon, the brunette vamp eventually reaches a breaking point and shuts off her emotions completely.
But by the time the finale rolls around, Elena is herself again — and ready to make a decision about which Salvatore she desires. Elena is understanding, but Damon simply cannot forgive himself and puts an end to the relationship. The final moments of the Season 5 finale come down to who makes it out alive from the collapsing Other Side. His quote describes this perfectly "you better not come back as a vampire or I'll stake you myself because I can't stand the thought of you hating me forever.
Damon is so sweet and protective of Elena here. Elena is convinced that the elixir will work but Damon isn't so sure and doesn't want to take the risk. You can really see her just how much Damon cares about Elena and doesn't want to lose her. I love her reaction to when he says "I can't lose you.
She says you won't which is trying to convince Damon that she isn't going anywhere. Elena in this moment realizes that she was wrong to slap Damon and she understands here why he made the decision to let Bonnie use her powers to try and kill Klaus.
I love how he said that if it comes down to her and Bonnie dying he will gladly let Bonnie die because "I will always choose you. This scene was so sweet. Damon finally admits to Elena that he loves her. He makes her forget telling her that he doesn't deserve her but Stefan does.
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