The relationship between the cured vampire/human doppelgänger, Elena Gilbert and the cured vampire/human, Damon Salvatore, is a complicated, but a popular and powerful romantic pairing, and a significant relationship in the series.
Though initially started on antagonistic terms, their relationship develops throughout the series.
When asked on the red carpet who he was most excited about seeing at the MMVAs, Ian answered, “Who am I most excited to see tonight? Ian and Nina are both way into helping out charities and are both huge music fans, so they have a ton in common.
She loses all feelings she has for him as a result, but continues a relationship with him solely for manipulation, later telling him her feelings were all due to the sire bond.Damon's willing to do anything to get her emotions back, including torturing her and killing Matt (although he was brought back to life), which eventually proved successful.Their friendship deepens, leading to them becoming best friends.Elena cares whether Damon lives or dies, and even when she chooses Stefan over him, Damon continues to still be there for her when she needs somebody and feels she can't turn to Stefan about it.This sends him off the deep end and he becomes guilty when he finds out the truth.
After he tells her the truth, they mutually decide to end their relationship as they realize they have too much control over each other. But after that, Elena tells Damon that he has to let her go until they can figure things out.
Stefan makes Damon realize how stupid he was acting and he decides to try and win her back.
However, when he finally tells her, he's unaware that Katherine has taken over Elena's body when she rejects him.
She later confesses this to him, stating that it's the most real thing she's ever felt.
After Jeremy dies, Damon uses the sire bond to get Elena to turn her emotions off, knowing that the pain would be too much for her.
He begins to fall for his younger brother Stefan's girlfriend, also Katherine's doppelgänger, Elena.