Though Damon and Elena had their first encounter during the pilot episode, the devilishly charming vampire thought he could woo his brother Stefan’s (Paul Wesley) crush with a kiss. The first time they kiss in the books happens in 'The Struggle'. With Tenor, maker of GIF Keyboard, add popular Damon And Elena Kiss animated GIFs to your conversations. Anne0791 649,143 views Damon is bitten by Tyler Lockwood, and quickly deteriorates from the toxicity of the werewolf's bite. Share the best GIFs now >>> In the Season 1 finale, Damon thought he kissed Elena but it turned out to be Katherine instead. Elena, moved by Damon's vulnerability, kisses the dying vampire before he is cured with Klaus' blood. 3x05 Damon & Elena "I promise you. This scene was one of the first moments that highlighted Elena's feelings for Damon. I will NEVER leave you again." last scene Vampire Diaries - Duration: 2:33. Elena and Damon shared their first kiss in season 2's "As I Lay Dying."