20 Most Iconic Elena Gilbert Moments

9. Losing Damon (5.22)

Oof. This was a rough one. Season 5 was up and down, but the end was certainly a lot – Stefan dying one episode prior to the finale, and Elena, Damon and Caroline all needing to fix that. Meanwhile, Bonnie’s dealing with the other side and well, you know how these things go. Our heroes were successful – mostly.

Aside from Bonnie and Damon not making it back from the other side, which is about to be destroyed into oblivion.

Maybe it was because we’d seen five seasons of pining, of tip toeing and of fighting feelings. Maybe it’s because we had finally come to a resolution the episode before between Damon and Elena, who spent the season butting heads and partly broken up for – really, not any good reasons. Maybe it’s just because Nina Dobrev knows how to cry and rip your heart out like no other, with a talent for it unlike any other. (Does that make it an iconic Elena moment or Nina moment? Either way, it stuck.)

Whatever it was, her breakdown when Damon doesn’t make it back after promising her he would, and the goodbyes they deliver each other though she can’t see or hear him (ghost, and all), destroyed me. Her cries and her broken voice, her sliding down the wall and curling into herself – it was too much to watch without crying right there with her. Her grief is too real, and it’s possibly the most hopeless we ever see her.

"“You lied to me. Please. Please come back to me.”"