|“||Yes, you are. And I'm never gonna be happy until you realize that you're never gonna have the life that you deserve if I'm in it. Goodbye, Charlotte.||”|
The romantic relationship between Damon Salvatore and Charlotte began sometime in 1942. Charlotte begged for Damon to change her into a vampire, which he did. However, she became sire-bound to him due to the fact she had genuine feelings for him as a human. Damon let her go after this decades later, which broke her heart.
Sometime in 1942, Damon and Charlotte met each other in New Orleans. After some time passed, Charlotte begged Damon to turn her into a vampire, and he eventually complied. However, an unexpected consequence of this decision was that Charlotte became sire-bound to Damon after he fed her his blood to turn her. It was noted that she was madly in love with him, which likely led to the sire bond.
When Damon and Charlotte were at a bar in that same year, Damon went to arrange for a musician to be her next meal. Before he left, he jokingly told her to not show any mercy to anyone who touched his drink, and when a fellow bar patron accidentally spilled his drink, Charlotte took his words literally and snapped his neck, killing him. When Damon returned to learn what had happened, he asked her why she would do that, so she reminded him of his parting words. It was this moment that led Damon to realize that she had developed a sire bond to him.
Damon knew he had to break Charlotte's sire bond to him, so he he found a witch named Valerie LaMarche, who convinced Damon she could break the sire bond. Unfortunately for them, Valerie tricked Damon into killing twelve innocent humans, claiming that it was necessary for the spell; however, she really had no intention of helping them, and instead used the sacrifice of the twelve souls to access a form of dark magic known as Expression.
Sometime later, Damon told Charlotte to count every brick in every building in New Orleans and that he would meet up with her in the morning on a corner, thinking the spell would have taken care of the sire bond by then. He then left town, and didn't return for nearly seventy years.
In We’ll Always Have Bourbon Street, Damon, along with Stefan arrived in New Orleans to find answers on how to break Elena's sire bond to him. Charlotte later found Damon on the street and kissed him, telling him that she knew he would return, and mentioning that she must have counted every brick on every building in New Orleans.
Another witch named Nandi, the daughter of Valerie LaMarche, later tells Damon that a vampire sire bond can't be broken by magic—the only way is to set the person free by insisting that they move on with their life without them. In 2010, Damon finally let a teary-eyed Charlotte free and the two both moved on with their lives.