Katherine had already lost measure of time and being in there seemed like forever. Every day, which was equal to a month, she kept seeing images of her daughter. They totured her, but not physically - that she could take. The demons had found her soft spot - humanity and used it against her. Now that she died as a human, her emotions were back and this only made her weaker despite the fact that life tought ther to be tough. Her family was there - in her nightmares, and even though she did not fear Klaus anymore, he was there too. Katherine, however, managed to stay strong a lot more than she ever expected. But it was only a matter of time before she stopped facing her past and started begging for murcy. This day had come - february the 2nd, 2015; this was the first time a quiet 'please' spilled out of her mouth. That made the demon change his form from Nadia to something even worse - herself. The "Katherine", immitating her voice said 'I like it when you beg.' The demon tilt her head the way Katherine used to do 'Soon or early they start to beg for murcy.' This hurt Katherine more than anything else when she remembered that were her words, she had said this many times

She was too weak to do or say anything, so she left the demon continue remind her all the terrible things she had done. Some time after, Two men got her attention - The king of hell himself and the new demon Dean Winchester. Katherine did not know who they were, but she listened very carefully to their talk. Dean seemed pissed off, while Crowley was giving him a lecture about how nothing can be undone. She felt a pitch in her stomach, and a few seconds later she realised she knew one of the men. Yes, that was Dean Winchester, Dean winchester who she once saved in purgatory while waiting to come back to life. These were the times Katherine was still a vampire, the most dangerous one. She wondered what got him in hell, and without realising she was staring at them, she continued trying to find out the reason. That staring got Dean's attention, who immediately stopped arguing with Crowley. He was tired of this anyways, and he had accepted his destiny. The only thing that was bothering him was his brother and the angel Castiel. When he saw Katherine's face he knew it was somehow familiar, but he couldn't remember where from. Dean had forgot the time she saved him in purgatory, in his eyes she was just another monster.

Suddenly an indea appeared in Katherine's head, an idea which seemed to be her escape from hell. She didn't even want to be a vampire again, all she was hoping for was to get out. She had noticed how demons oferred the other people in hell to end the toture and become demons too, so she waited for an offer like that. But no such thing happened - the toture only continued, without the demons saying a word. She was ready to become one, making people suffer was something she was trained well at, but she never got the chance. And now that chance was standing near her - the boy who owed her one, life for life. Katherine tried to call his name, but all that got out of her mouth was a quiet groan. She took a deep breath and said his name. Dean only hear a part of it, which made him turn into Katherine's direction. That made her think he heard her, but when he decided it was nothing, Katherine's hope for life disappeared. However, she was a warrior who did not gave up easily, so she said his name one more time. Dean searched for the source of the sound once again, and when he found it he went towards Katherine 'I know you. You-you saved me in purgatory. Why aren't you there?'
Crowley appeared surprised by the fact that they knew each other which made him laugh. 'She's a human now. You maybe saw her in purgatory during the time she was one of the evilest bitches on earth, and now she's rotting here, experiencing things worse than dying. Oh, how she only wishes she was dreaming, don't you, darling?' Katherine looked at the man unknown to her and she didn't realise how he knew who she really was.

Dean came closer to Katherine, examinating every part of her face. She looked completely different from the first time he saw her - the dark eyeshadow was gone, the red lipstick wasn't on her lips anymore and dark circles covered the skin under her eyes. No matter how bad she looked, she was still beautiful - even in a demons eyes. Katherine noticed she got Dean's attention and her hopes went up again - this could be her chance for life and all she had to do is convince him to help. She manipulated people her whole life,which made her think this wont be difficult this time either, she had to choose what to say very carefully.
'Do you want her, Dean? She's yours, do whatever you want to, but be careful - she takes pain. This is a good start for a noob demon.' Crowley laghed to his own joke, and Dean looked at him - 'Crowley, I don't want to toture anybody! Cancel that spell, I need to get to my brother and Cas. God knows what they're thought when they saw the missing body!'
'Oh, don't worry about that, squirrel. Your brother buried you himself. What, are you surprised?' Katherine looked at Crowley, realising how much they are alike - both hurt people with and without words.
'Okay, I'll take her.' She wasn't afraid of him, this was the perferct chance to make him help her.

From that day on, Katherine no longer had to see her past over and over again. Dean would just stand there, doing nothing, and not tell a word to her. He would stare into the nothingness, completely silent. This bothered her, because the last flash of hope slowly faded away - she needed him to talk first in order to convince him. The days passed on, and it was a month until Dean finally said something to her- 'I'm sorry.' Katherine was surprised, but she asked with a low voice 'For what?'
'I'm sorry about your daughter.'
He hit her soft spot, Nadia.
'You know nothing about her, you don't have to be sorry for anything. Now, please, go on with doing nothing, if you wish.'
'Oh believe me, I know. The demons showed me your awful past, and I gotta admint, it's pretty dark. I am supposed to be toturing you right now with that past, remember?'
'Then why aren't you?'
'Because I know how it feels.'
This was her opportunity, this was her only shot to make him help. In Katherine's eyes, Dean was her saviour; the one who was about to end her misery and she had to play her cards well.