Damon Salvatore and Elena Gilbert were one of the most popular pairings in The Vampire Diaries. The two were initially entangled in a love triangle with Damon's younger, also vampire brother Stefan. Despite her love for Stefan, Elena falls in love with Damon throughout the series and Delena shippers everywhere rejoiced when they reunited in the series finale.
Damon and Elena's romance was epic but many other characters would have been more suited with the older Salvatore. Damon shared sexual tension and, occasionally, genuine respect with several other people. In hindsight, maybe he should have been with these characters instead...
Rebekah Mikaelson
Damon and Rebekah hooked up for the first time in season three of The Vampire Diaries. The vampires shared a steamy affair that ended badly when Damon betrayed the Original. Rebekah tortures the Salvatore brother in revenge and their passionate romance comes to a bloody halt.
Rebekah seemed to genuinely care for Damon at times and the two vampires shared a significant amount of chemistry. It would have been interesting to see Damon and Rebekah together in New Orleans in The Vampire Diaries' spin-off show The Originals.
Bonnie Bennett
Damon and Bonnie became unlikely friends in season six after they were trapped in the 1994 prison world. Their friendship is one of the most authentic relationships in the series and is further explored in the later seasons of the show.
Bonnie has a similar role to Elena in Damon's life. The Bennett witch inspires him to be a better friend and a better person. Damon and Bonnie share sexual tension in the books and many fans were disappointed when this wasn't adapted for the series.
Katherine Pierce
Katherine Pierce was Damon Salvatore's first love and, in many ways, is responsible for the person he became. Katherine manipulated Damon and Stefan and turned both brothers into vampires. Damon believed Katherine was trapped in the tomb for over a century and is heartbroken when he realizes that the vampire never loved him.
Katherine ultimately only loved herself, but like Rebekah, she was a powerful figure who shared sizzling chemistry with the older Salvatore brother. Damon had more in common with Katherine than Stefan did.
Isobel Flemming
Damon turned Elena's mother and Alaric Saltzman's first wife Isobel into a vampire before the events of the series. This comes to light when Isobel returns to Mystic Falls. Elena's mother conspires with John Gilbert to keep her away from the Salvatores before later betraying her for Katherine.
Isobel learned a lot from her sire and the two almost had a steamy reunion in season one before Damon warns her away from Elena. Like Katherine, Isobel had more in common with Damon and the two had undeniable chemistry.
Rose
Rose was one of the few people in The Vampire Diaries who Damon undeniably cared for. He first meets the older vampire in season two and discovers that she inadvertently sired Katherine. Damon and Rose are romantically involved until she is killed by a werewolf bite.
Damon had a great deal of respect for Rose and their relationship felt more equal than his romance with Elena. It would have been interesting to see if Damon still ended up with Elena if Rose had survived.
Andie Star
Damon initially manipulates Andie with compulsion but grows to care for her throughout their relationship. They first meet in season two and are love interests until the third season. Stefan compels Andie to jump off a stage, killing her in front of his brother.
Andie's death is tragic and further highlights Stefan's fall from grace. Damon grew to care for Andie but ultimately could not move past his feelings for Elena.
Alaric Saltzman
Alaric Saltzman is Damon's best friend and former drinking buddy. The two have a chequered history; Damon turned his wife into a vampire, causing Alaric to become a vampire hunter, and has killed his friend more than once. Despite this, Alaric is one of the few people who understand Damon the most and isn't afraid to stand up to him.
Damon grows to respect Alaric more throughout the series and is distraught when his friend dies in season three. Luckily, Alaric returns to the land of the living after the Other Side is destroyed in season five.
Sage
Sage is a minor character who appears briefly in season three of The Vampire Diaries. She is revealed to have had a similar influence in Damon's life as Lexi had in Stefan's - though the redheaded vampire was far more sadistic. Sage encourages Damon to enjoy life as a vampire and has a steamy hook-up with him after helping him betray Rebekah.
Sage's heart ultimately belonged to Finn Mikaelson and Damon was irrevocably in love with Elena. However, Sage and Damon had a passionate romance. Sage challenged Damon and was an influential and important figure in his life.
Enzo St. John
Enzo is first introduced in season five of The Vampire Diaries. The former Augustine vampire was Damon's best friend until Damon left him to die. Their friendship is rekindled when they are ensnared by the siren Sybil in season eight.
Like Alaric, Enzo understood Damon and wasn't afraid to challenge him. They could have left the drama of Mystic Falls behind them forever and set off to have adventures across the country of their own.
Lexi Branson
Lexi was Stefan's best friend until she was murdered by Damon in season one. She helped Stefan control his bloodlust and live peacefully as a vampire. We learn in season four that she attempted to help Damon and shared a brief love affair with the older Salvatore brother until he betrayed her.
Lexi was strong, powerful, and sure of herself. It would have been great to see her stick around for longer and challenge Damon throughout the series.