Elena and Damon officially get together in The Vampire Diaries Season 4, Episode 7 ("My Brother's Keeper"). This marks the beginning of their romantic relationship when Elena becomes a vampire and starts to trust Damon more than Stefan. They spend the night together and become physically intimate, which is a pivotal moment for their relationship. Following this, in Season 4, Episode 23 ("Graduation"), Elena breaks the sire bond and sincerely confesses her love for Damon, solidifying their relationship. Earlier in the series, Damon admits his love for Elena in Season 2, Episode 8 ("Rose"), but they do not start dating then. Their first real kiss happens in Season 2, Episode 22 ("As I Lay Dying"), during a moment when Damon is gravely injured. However, their official romantic relationship begins in Season 4 after Elena's transformation into a vampire and her decision to be with Damon over Stefan.