In the early seasons of The Vampire Diaries, Damon and Elena are the ultimate will-they-won't-they couple. Elena is Damon's brother's girlfriend. Sometimes Damon is Elena's friend, sometimes he's her enemy. But no matter their situation, one thing stays the same: tension.
With such undeniable chemistry, the road to the pair finally uniting in season 4 is marked by plenty of charged moments. On occasion, they even come dangerously close to crossing the line for good, only to pull back at the last moment.
Damon Tells Elena He Loves Her
Elena and Damon's relationship in early season 2 is pretty much non-existent. With Damon having betrayed her trust by not only trying to kiss her but killing her brother (temporarily), Elena insists that he's lost her forever.
But Damon's feelings remain as strong as ever. Upon returning her necklace one night, he finally reveals the truth: he loves her. It's clear that Elena is shocked – and moved – by the revelation, and there's no saying how she would've responded if Damon hadn't erased her memory.
The Day Of Elena's Parents' Accident
When Elena chooses Stefan over Damon in the season three finale, she remarks that – had she met Damon first – their relationship might have been different.
Unbeknownst to her, however, she actually did. It's revealed that the night of her parents' accident, Damon mistook Elena for Katherine before the pair had a flirty conversation on the road. Elena is obviously interested, and without Damon erasing her memory (again) this connection would've had a stronger start than even hers and Stefan's.
The Kiss In The Motel
Challenged by Stefan over her feelings for Damon, Elena uses their trip to find Jeremy in Denver to explore their connection. Sharing a room at a motel, the sexual tension three seasons in the making finally culminates in Elena rushing to make out with Damon in the hallway.
This could have gone further if Jeremy hadn't interrupted. The shock pulls Elena out of the moment entirely, ruining what might have been the first step into a more official relationship.
Elena Learns How To Feed
Elena's life changes completely when she becomes a vampire. With Stefan unable to accept her new self, Damon steps in to help her learn how to feed properly, taking her on a research trip of sorts to Whitmore College.
At a college Halloween party, this bloodlust quickly evolves into something else. They share a dance on the verge of something much more – until Bonnie interrupts. Until that moment, they're completely under each other's spell and would otherwise easily have gone further.
Damon Asks Elena Whether She Has Feelings For Him
Elena's feelings for Damon are obvious to everyone before they're obvious to her. While on her road trip to Denver in season 3's "Heart of Darkness", he finally asks her point-blank how she feels and whether she was hoping he'd mess it up before she had to decide.
Her response comes close to touching on her feelings directly, although she doesn't completely manage it. But some more clarity or space to explore her emotions, this could have been the moment.
Elena Decides Whether To Drive To Stefan Or Damon
In "The Departed", Elena is leaving Mystic Falls with Matt when she insists that he take her back home, where Stefan is waiting.
But it didn't have to be this way. She could just as easily have continued driving on to where Damon was waiting in a storage unit with Klaus' body. Had she done so, not only would she and Damon have started dating much earlier. It's also likely she wouldn't have become a vampire.
Damon Admits It Isn't Their Time
Having properly kissed for the first time in the previous episode, Damon and Elena are in a new stage of their relationship in season 3's "The Town" – even if it isn't yet fully romantic.
There's a moment at the end of the episode, however, where there's an opportunity for them to kiss again, or even discuss their relationship. Instead, Elena tells Damon he can't kiss her, insisting that it isn't right, to which Damon insists it's just not right now. A classic example of the right person, wrong time.
Elena And Damon Let Stefan Go
After Stefan leaves with Klaus in the season 2 finale, Damon and Elena spend the early stages of the following season trying to find a way to get him back. In the meantime, the two grow much closer – veering further towards romance than ever.
Perhaps the most symbolic moment comes when Elena emphatically tells Damon that they'll let Stefan go. Hands-on the sides of his neck, they come dangerously close to kissing. But, as always, they're interrupted – just as they might've been willing to forget about the Stefan-shaped obstacle between them completely.
Elena's 18th Birthday
It's only in season 6 that Elena reveals this to be the moment she realized she loved Damon. However, it's pretty obvious even upon the first watch in season 3 that there's tension between the pair just waiting to be broken.
To celebrate her 18th birthday, Damon regifts Elena with the necklace from Stefan she'd thought lost forever. It's one of Damon's rare, sweet, selfless actions. If Elena wasn't quite as guilt-ridden, there's no doubt that this act alone could've brought Elena and Damon together.
The Entire Summer Without Stefan
In the summer between seasons 2 and 3, Stefan is not only absent but deep in a Ripper spree. This leaves Elena and Damon free to grow closer than ever – with everyone from Alaric to Caroline eventually commenting on their increasingly flirty relationship.
With a whole summer alone together, there are countless moments where the pair could've crossed the line. This is undoubtedly the shifting point of their entire relationship. Without their mutual fixation on tracking down Klaus, it could've been even more monumental.