Annette Brown/The CW
Samantha Highfill
January 29, 2016 AT 04:11 PM EST

Damon Salvatore is a complicated man. He’s dangerous, he’s impulsive, and sometimes, he’s downright stupid. But he’s also sweet, loyal, and when push comes to shove, compassionate. He just doesn’t always make the best decisions in emotional situations. 

For example, that time he snapped Jeremy’s neck after Elena told him she loved Stefan. Or that time his mother was dying and he was still so upset with her that his final words to her were, “You made your bed. Have a nice nap.” All of this is to say that Damon Salvatore’s time in the Phoenix Stone — which is known to punish vampires for every bad thing they’ve ever done — isn’t going to be easy. 

It will, however, give The Vampire Diaries an opportunity to do something the show’s never done before: A concept episode. Focusing in on Damon’s personal hell — which is set against the backdrop of his time in the Civil War — executive producer Caroline Dries tells EW that the writers knew that if they were going to try a concept episode, they had to go all in. “[Damon] really is driving the entire story from beginning to end. We are in Damon’s mindset through a journey that is frustrating and kind of funny and grueling.”

As to why the writers chose Damon to go through this experience, Dries says, “With him what’s interesting is you saw where he had the opportunity to tell his mom that he forgives her, [and] he tells her, ‘You made your bed, have a nice nap.’ So that is the character that you want to see realize that he’s messed up a few times in life. A character like Damon is so resistant to change but that’s what makes him interesting to watch, as opposed to a character like Caroline or Bonnie or these sort of heroes of the story. They’re much more in tune with their feelings and they regret things more obviously.”

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Stuck inside his own “custom-made hell,” as Dries put it, Damon will be confronted with experiences and people from his both his distant and his recent past. After all, as longtime fans will remember, Damon was still human when he served in the Civil War, so we can expect to see a bit more of who he was before Katherine Pierce entered his life. And yet, at the same time, he’s also the Damon who just basically spat in this mother’s face. So naturally, those unresolved issues will continue to haunt him. As Dries says, “Hell is trying to convince him to change.”

The worst news of all? Damon’s three months in the stone is only the beginning. “When we do something huge on the show — like punishing a character for an entire episode — there needs to be some ramifications that come out of it, so things will only get worse, unfortunately, for Damon and Stefan,” Dries says.

And it’s not just Damon and Stefan who will be affeted. “Our characters will be changed and there will be massive moves that happen in the story that have gigantic ripple effects,” she adds. “We have one half more of a season to fix it all, but it’s looking pretty bad right now.”

The Vampire Diaries airs Fridays at 8 p.m. ET on The CW.

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