“I promised you an eternity of misery, so I’m just keeping my word.”

Or when Elena Gilbert said, Theres more to me than just gloomy graveyard girl?

I promised you an eternity of misery, so Im just keeping my word.

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The CW

The line perfectly showcases Damons intentions, setting him up as the bad guy in Season One.

Dear Diary, a chipmunk asked me my name today.

I told him it was Joe.

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That lie will haunt me forever.

Damons sardonic side came through when he mocked Stefans journaling habits in the early seasons ofThe Vampire Diaries.

Damon became an expert at masking his feelings behind a facade of nonchalance.

What better way to make people think you dont care when you actually care too much?

This line is pure Damon Salvatore, with just enough self-awareness to make it irresistibly endearing.

We never really know if hes genuinely a Swiftie or just using it to seem approachable.

Ive been in love.

Its painful, pointless, and overrated.

But as viewers got to know him, it became clear that this wasnt a casual brush off.

Damons words came from an emotionally broken person who loved deeply and had his heart shattered beyond repair.

Its a rare moment of vulnerability hidden behind his usual bravado.

Because for Damon, love isnt just a fleeting emotion.

Its a wound that never heals.

Damons defiance, in this instance, isnt just about rejecting the good guy label.

Its about the crushing weight of expectations that come with it.

I would rather spend every moment in agony than erase the memory of you.

Thats what made his confession to Elena so endearing.

It speaks to the kind of love Damon had for her, which was unconditional and unrelenting.

Despite their troubles, Damons loyalty to Stefan never wavered.

Damons words proved that beneath his cynicism was a heart capable of love and sacrifice.

Hello, brother.

In the pilot, its laced with venom to remind Stefan of their fractured bond.

But in the series finale, the same line is said with love.