<P> The Five, shows Damon tasking Stefan with learning more about the Vampire Hunter, Connor while Damon decides to accompany both Bonnie and Elena to College . This trip is ostensibly about teaching Elena the' hunt': how to catch, feed and erase . After some initial problems, Elena has a Frat Party gets success and seems to enjoy herself causing friction with Bonnie . She leaves the party and later states that she doesn't want to be like Damon . In the next episode, she begins to believe that Stefan is lying to her and takes things into her own hands to kill the vampire hunter who is holding her brother, Matt, and April captive . She does, and begins to suffer from hallucinations at the end of the episode . After asking Stefan why he wants to cure Elena, Damon tells him that he loves Elena as a vampire or human . </P> <P> In the episode' We All Go a Little Mad Sometimes', Damon helps Elena in dealing with her hallucinations and saves her from committing suicide . He also helps uncover the mystery about the hunter's curse with the help of Bonnie and Professor Shane . At the end of the episode, he reveals the truth about the cure to Elena and explains how Stefan has been lying to her only to find this possible cure for vampirism . However, Elena breaks up with Stefan at the end of the episode after confessing her gradually growing feelings for Damon . </P> <P> In the following episode "My Brother's Keeper", Elena tells Damon he is the reason she and Stefan broke up and at the end of the episode Damon and Elena finally have sex . After that it turns out Elena is sired with Damon, first they think it is the reason why Elena loves Damon, but in episode "We'll Always Have Bourbon Street" they found out that it only affects how you act, not how you feel . The sire - bond can only be broken when Damon leaves Elena and tells her to stop caring about him according to a witch in New Orleans named Nandi . In the following episode Damon goes with Elena to her family's lake house to help with Jeremy's Hunter instincts . In the episode Elena tries to act like a couple with Damon, but he refuses to even kiss her out of his guilt about the sire bond and worry that he's taking advantage of her . In the end of the episode Damon invokes the sire bond telling Elena to return to Mystic Falls while he trains Jeremy "O Come, All Ye Faithful". Elena kisses him goodbye . </P> <P> In' After School Special', Damon is at the Lake House training Jeremy, along with Matt Donovan . Klaus shows up and threatens Damon, wanting him to get Jeremy's mark completed earlier rather than later . Damon is shown to be reluctant, not wanting to hurt innocents for Elena's sake, but Klaus follows through with his plans regardless . Later in the episode Elena calls Damon and confesses she's in love with him and it's the' most real thing she's ever felt in her entire life', in a moment of weakness Damon tells her to come see him . Afterward Damon is confronted with a bar of newly turned vampires for Jeremy to kill concedes that it's the quickest way, however balks when Klaus takes control and compels the newly turned vamps to kill Matt Donovan . In Catch Me If You Can Damon tells the boys to run since Jeremy isn't ready to take on all these vampires . Later when Elena arrives her and Damon argue over the killing of innocents and tells her to take Matt home while he and Jeremy take care of Klaus's newly turned vampires . However Kol shows up and has killed all the vampires, determined to stop them from finding the cure & waking Silas, and threatens Jeremy's life . Kol compels Damon to stake himself and later to kill Jeremy and to forget what Kol compelled him to do . Upon arriving back in Mystic Falls Damon begins to seek out Jeremy due to the compulsion, however when he sees him in the grill he realizes what Kol compelled him to do and tells Jeremy to run . Damon chases Jeremy throughout Mystic Falls and advises Jeremy that he is compelled and he needs to kill him . Jeremy shoots Damon in the head and when Damon awakens later starts cursing the youngest Gilbert, calling him stupid for not killing him . At the end of the episode Damon catches up with Jeremy Elena follows and urges Damon to fight it because "You love me and I love you", but he tells her that he can't, falls to his knees and urges Jeremy to kill him . Stefan shows up just in time to break Damon's neck and lock him up until they can take care of Kol . Damon spends the next episode locked up and bled dry by a jealous and snarky Stefan and engages in a conversation with Klaus about Caroline, Rebekah and Elena . </P>

When do damon and elena first sleep together