4. Kissing Damon at the motel (3.19)
It was the kiss so many shippers and fans had been waiting for for three seasons – the kiss heard around the world. It wasn’t their first kiss – not even their second – but it was epic, nonetheless. It was Elena making the first move, and not because Damon was dying, not because of anything life or death. She was finally giving in to the feelings she’d been fighting for so long.
Set the backdrop of Florence + The Machine’s “Never Let Me Go”, it is to this day one of the steamiest TV makeouts of all time – but more than that, it was Elena acting on feelings, finally just being. She saw the good in Damon, and she called him on that. He wasn’t bad – and she saw that. She saw him for who he was, who he could be, and he brought out a side of her that wasn’t thinking about everyone else all the time. Like Rose says to Jeremy later in the episode – they’ll either be the best thing for each other, or the worst thing for each other.
But it’s iconic mostly because this was Elena’s move – she kissed him first, for the first time, and there was no more denying it. She felt something for him, and for just a minute, she let herself feel those feelings.