Damon and Vivienne

The relationship between Damon Salvatore and Vivienne Pierce has been complicated since their meeting in 1864, when Vivienne stayed in their estate and Damon was serving in the Confederate army. Damon fell deeply in love with Vivienne. Their relationship ended when the town began eradicating the vampires. She was then taken away, and Damon was shot by his own father while in an attempt to save her, causing him to turn into vampires. Damon since then, has spent the following 145 years obsessed with freeing her from her tomb, only to find out that she was never in it in the first place.

Vivienne returns to his life in The Return. Damon initially acts flippant towards her, however she seduces him before telling him that she never loved him. Throughout the following seasons, Damon's feelings for Vivienne have dwindled while Vivienne still attempts to seduce him from time to time. It is later revealed that Vivienne had in fact loved him, but would ultimately choose her and Katherine's safety over him.

Trivia

 * While Damon claimed many times that his love for Vivienne was real, it's unclear if it is true:
 * The fact that while Damon declared Vivienne never compelled him, it proved to be false in a flashback.
 * Vivienne twice admitted that she loved Damon:
 * To Elena in As I Lay Dying.
 * To Damon in Memory Lane.
 * The relationship between Damon and Vivienne is actually the most tragic and most complicated relationship. From love to hate just in one second. Also, Vivienne once said "Love, hate, such a fine line"