Content Warning: This article contains mention of abuse and sexual assault.
Because of his humor, devotion to Elena, and redemption arc, Damon Salvatore was the most popular character when The Vampire Diaries was airing. He'll probably always be the standout, given his dynamic and entertaining personality. Damon took a cheesy, supernatural romance and made it a borderline dramedy.
He's responsible for some of the funniest scenes in The Vampire Diaries, and the show wouldn't have survived for so long without him. Although Damon is a vital presence, it's become obvious during rewatches that he's not as great as viewers initially thought. Supernatural dramas require some leeway, given how far removed they are from reality, but there's no excuse for the offensive comments Damon made during the series.
"What You Want Is The Little Blonde Pretty Girl. Self-Absorbed, Easily Flattered. You Just Have To Separate Her From The Pack And Make Your Move."
This quote was easy to overlook when it was first said. Damon was trying to help Elena find the perfect person to feed on, but his entire ideology is sexist. He made the assumption that the girl was self-absorbed and easily flattered just because she was pretty and blonde.
Damon's explanation of how he chooses his victims gets worse after remembering what he did to Caroline. Damon eavesdropped on her conversation in the pilot and used her low self-esteem to his advantage. He preyed on, abused, and manipulated her, and displays the same misogynistic and toxic behavior years later.
"Elena Would What? Hurt Me? Dump Me? Been There, Done That!"
A large argument among fans is whether or not Damon deserved redemption. While Elena is Damon's best relationship in The Vampire Diaries, it doesn't mean that it was healthy. Redemption arcs are influenced by outside factors, but at the end of the day, the desire to change needs to come from within.
After Katherine pretended to be Elena and broke up with Damon, Damon reverted back to the person he was before they started dating. This quote alone is proof that Damon only kept himself in check because he wanted Elena, not because he wanted to be better.
"Because Katherine Is A Manipulative, Nasty, Little Sl*t."
This isn't the only time Damon has called Katherine a "sl*t," as a way to insult her. There are plenty of bad things to say about Katherine, given how selfish and conniving she can be, but Damon decided to take the misogynistic route.
It's made even more sexist by the fact that Damon has slept with plenty of women, but only appears to see it as a bad thing when Katherine does it. Supernatural show or not, there's nothing okay with a man sl*t-shaming a woman.
"Sure She Does. They All Do. They're Whatever I Want Them To Be. They're Mine For The Taking."
Damon calling Caroline his puppet was disturbing on multiple levels. He held her against her will, compelled her into a relationship, and had sex with her.
It's possible that Damon was referring to everyone, regardless of gender, when he was talking to Stefan, but it doesn't make it any better. He saw Caroline as an object that existed for his own pleasure and convenience. To make matters worse, Elena paints Caroline out to be the bad guy for disliking him.
"You Want Me. I Get To You. You Find Yourself Drawn To Me. You Think About Me Even When You Don't Want To Think About Me. I Bet You Even Dreamed About Me. And Right Now...You Want To Kiss Me."
Elena is often the only person who is exempt from Damon's malicious behavior. However, it's easy to forget that early on, he had no problem manipulating her and using compulsion to force her to consent.
Damon said this to Elena after he used his abilities to make her dream about him in a sexual context. He compelled her to kiss him as a way to anger Stefan, and he would have succeeded if Elena wasn't wearing vervain. It's unclear whether or not Elena came to realize what Damon had attempted to do.
"You Are The Only Stupid Thing Here. And Shallow And Useless."
The complete malice in which Damon said this to Caroline was enough to make anyone dislike him. Caroline was only sixteen at the time, and even after everything Damon did to her, she remained loyal to him.
Caroline never felt like she was good enough, and Bonnie and Elena acted like she was an annoying child rather than an equal. The way Damon treated Caroline, and women, in general, is just one of the many reasons people believe Damon didn't deserve redemption in The Vampire Diaries.
"I Need You To Put Me Down As A Chaperone At The Dance Tonight."
There's nothing wrong with this quote out of context, as the issue lies within the implication. The show completely ignores how much older Damon is than the rest of the characters, which makes it all the more creepy. While arguments can be made about everyone's age given the premise of the show, Damon was 25 in human years.
During this time he was in a relationship with Caroline and publically attending events with her. Volunteering as a chaperone was the only way Damon could get into the high school dance, and to the outside world, he was Stefan's legal guardian. Jenna was closer in age to Damon than Elena was, and she would have been a more age-appropriate love interest.
"You're Lying To Me. And You're Lying To Stefan. And Most Of All, You're Lying To Yourself. I Can Prove It."
In one of his worst scenes, Damon tries to physically force himself on Elena. The Vampire Diaries try to make it more justifiable by reminding viewers that Damon was drunk and Katherine had just broken his heart. Yet that doesn't give Damon the excuse to sexually assault a woman, especially one that he claims to love.
Damon refused to believe that Elena didn't have feelings for him, and he seemed to think the only possible reason she wouldn't is that she was lying to herself. There's no doubt that the two had formed a bond, but Elena wasn't obligated to return his feelings. Even if she did, it wouldn't be an excuse for Damon to kiss her after she said no.