Damon was the main womanizer and heartbreaker of The Vampire Diaries. While Elena eventually became the love of his life and the reason he turned human again, the older Salvatore brother had many affairs that really shaped him as a character.

Here are five of Damon's girlfriends who, in one way or another, helped understand better the most controversial character of The Vampire Diaries.

This is an affair that left fans with one question in mind: "God, why?" Rebekah had a full-fledged romance with Stefan, but she also had a passionate one-night stand with Damon that did not end well for either of them.

Damon used Rebekah to learn more about white oak trees. When the original vampire found out about the betrayal, it all ended as it usually does in The Vampire Diaries — with torture.

A little fling with Caroline showed us Damon who went through Sage's school and accepted her philosophy that love and sex were not the same thing.

In season 1, Damon and Caroline's relationship was unhealthy, to say the least. Caroline liked Damon, but he used her as a walking blood bank and an easy way to get closer to Elena.

Damon took the girl’s blood against her will, insulted, and terrorized her. When he got bored, the vampire even tried to kill Caroline. Luckily, Stefan was nearby.

Andie was a charming reporter who tragically died right in front of Damon. The relationship with Andie was a perfect middle ground where there was an imprint of spiritual intimacy in addition to sex.

They resembled a stable and even a little boring couple who had been together for a long time. Why was it important to show this relationship? Because it was Damon’s way of trying to live a normal person's life.

In 1864, both Stefan and Damon fell in love with Katherine, and their devotion to her completely changed the course of their lives, pitting them against each other for up to 145 years.

Damon undoubtedly gave up humanity for the sake of eternity with Katherine, and when he thought she was in the tomb, he remained faithful to her for more than a century, searching with all his might for a way to save his beloved.

At first, Damon was only interested in Elena because of her resemblance to his first love, but then the older brother realized that Katherine had always loved Stefan and was only using him.

Damon and Rose had a very special relationship. For the first time, we saw a deep, gentle, selfless Damon, and all thanks to Rose. Like Elena, she was able to bring out the best in the older brother.

Rose is the woman who showed Damon his humanity after Katherine's betrayal. And her appearance in his life was the deciding factor in restoring much of his trust in women. It was after the talk with Rose that Damon's humanity switched back on.