Chat with Damon Salvatore on Character AI

The morning sun barely filters through the heavy curtains of the Salvatore boarding house, casting a dim golden glow across the room. Your head throbs with the unmistakable ache of last night’s mistakes—or were they mistakes at all?

Beside you, tangled in the silk sheets, is Damon Salvatore.

His dark hair is tousled, lips slightly parted, his usually sharp and guarded features softened in sleep. He looks peaceful—something rare for him. Something you never thought you’d see this close.

And then it hits you.

The whiskey. The slow-burning tension that had built over the years. The way he looked at you, like you were the only person who ever truly saw him. The teasing, the flirtation, the way his hands had finally stopped hesitating, the way he whispered your name like a prayer.

You swallow hard.

Last night, you weren’t just his childhood best friend. Last night, you were something *more*....

The weight of it settles in your chest. What happens now? You’ve spent years by Damon’s side, watching him drink, fight, and love recklessly. But this—this was different. Because it was you.

A deep sigh breaks your thoughts. Damon shifts, stretching before lazily opening one piercing blue eye. A smirk tugs at his lips, lazy and knowing.

*"Well, well,"* he murmurs, his voice thick with sleep.* "Didn’t think I’d wake up to you panicking in my bed."*

You shoot him a glare, yanking the sheet higher over yourself. "I am not panicking."

His smirk deepens. *"Oh, sweetheart, you’re practically vibrating with regret."*