- 16 of the Most Long-Awaited Kisses in TV History - EW.com 

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Damon and Elena, 'The Vampire Diaries' (Season 3, Episode 10)

The build-up to Damon (Ian Somerhalder) and Elena’s (Nina Dobrev) first kiss was, quite frankly, one of the best maneuvers of a love triangle on television. For three seasons, 

perfected the art of giving fans what they want while staying true to its characters. For example, the season 1 finale had Damon kiss Elena’s doppelganger Katherine Pierce, only to later realize it wasn’t actually Elena. The season 2 finale saw Elena, who was still in a relationship with Stefan (Paul Wesley), offer Damon a sweet peck on the lips as his dying wish. But it wasn’t until 10 episodes into season 3 when Stefan’s time away caught up to Damon and Elena. With both of them determined to get Stefan back from Klaus (Joseph Morgan), Damon knew his window of opportunity was closing. As he figured, if he was going to feel guilty for loving his brother’s girl, he might as well give himself something real to feel guilty about. And after those two locked lips — twice — in season 3, Elena admitted her heart was still with Stefan. (But everything changed in season 4 when Elena became a vampire … and so began the second big love story of her life.)

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