Castiel kept his promises. He freed Ruby from The Empty but didn't know why. He was equally mystified when Dean didn't protest. Jack had no opinion, but Sam looked startled. Ruby was standing in the bunker. It was Jack that negotiated with The Empty for Ruby. Not even Death knew she came back.
Ruby rolled her eyes seeing the men staring at her.
"What. You didn't say anything about Feathers here." She says pointing at Cas. "Don't worry, I'm not Lilith, I am not God's bitch." She smirked at Sam. "Hey you. How's the big lug."
"Fine Ruby. What do you want." He still distrusted her. He still felt the pain of her betrayal.
"I been dead for years. I can really use some french fries. Mind if I eat some?" She smiled a small smile at Dean.
Later that night, Ruby was sitting on the chair waiting for Dean. Sam, Castiel and Jack were out seeing a movie. Dean told them he was keeping an eye on the demon bitch. Ruby rolled her eyes at the insult, but knew exactly why Dean told them that. She was getting cured. Dean payed a reaper to escort Ruby upstairs. He had to hurry, if Billie found out, she was going back in The Empty.
"Winchester. After everything I done, you are going to do this. Why?"
"A promise is a promise. Besides. Jonathan is waiting. Same with your aunt."
Ruby just smirked. She had no idea what humanity felt like, not after all this time, but she was excited.
"At least I don't have to see Ashley again. Or Lilith. I hated them both. Ashley tortured me more than Alistair." Ruby shuddered at the memories.
"Well, you helped Cas, therefore helping us. You deserve it."
"Bullshit. But I appreciate it. So, will this hurt?"
"Yes." Dean still remembered his cure. It felt like hot lava in his arms. But that wasn't the worst part, it was his humanity. It hurt more than anything in Hell.
"Just get this over with."
Castiel came back because he needed to make sure Dean wasn't getting hurt. The bunker echoed with Ruby's screams. He heard the cure was agonizing for demons. He shuddered at the next few screams, the next one worse than the last. But he can hear her humanity coming back.
Ruby had tears running down her face. Oh god. The guilt on what she done. The people she hurt, the man she loved. He was standing in front of her. Dean eyes were shiny, he knew after the next vials, Ruby would be cured. A reaper was already in the room ready to take Ruby upstairs. Michael gave his permission. Dean was staring at Ruby. No Matilda. Dean was going to kill her, but Ruby said she knew she was going to die.
"You better hurry. I sense Death. She is on Her way." The reaper warned.
Ruby screamed as Dean gave his second to last vial. The final step was his blood, straight from his hand. But before he cut his hand, he asked Ruby if she was okay with everything.
"Yes. I sense Jonathan. He is waiting. Dean. Thank you." Dean just gave her a sad smile.
"Tell my great gramps I said hi. Okay. This is it."
"Dean. No Winchester. Thank you. I'll see you soon. I'll cook you authentic Italian pizza. I'm ready."
Dean had to look away when Ruby was cured. The light, it was bright. Like an angel's grace. Her soul. It was purified. Ruby was groaning when she became human. But she was bleeding from her nose and mouth.
"Dean." She groaned. "Hold me." Dean held her in his arms, just as Sam and Jack came running in hearing Ruby's screams. ''Thank you. Sam? Is that you." She groaned.
Sam came walking over, still distrusting Ruby. But seeing Dean crying, he wondered what happened.
"Forgive me. For everything." She gasped. "I meant what I said. I remembered being human. Sam, don't fall in love too quickly. You never know who is authentic." She coughs out blood.
''Dean. Tell that angel of yours thanks. For keeping his promise. Listen to Ray Charles for me." She said with a tear running down her cheek. "Dean, come here." When Dean came close, she whispered. "Italy will still be there." She died a few seconds later.
When Dean got up the reaper was gone. His face neutral, he ordered Jack to hide Ruby's vessel. Just in time, Billie came in.
Matilda smiles seeing her home. She smelled pizza. Her husband must be home. Good thing too, she was starving.
"My love."
"Jonathan." They run into each other's arms.
Dean was drinking a whiskey listening to Ray Charles. They already burned Ruby's vessel, the girl could finally rest. Billie demanded why they broke the rules. Dean just said he never broke a promise. God Himself said the same thing. Billie was fuming, but there was nothing She can do. Both God and The Empty allowed it.
"Hey Sam!"
"What?"
"How do you feel about a vacation. We can invite our doubles to stay in the bunker while we go to Italy. Jack agreed to fly us."
"Sounds good to me!"
Dean looked up and saluted Ruby.
"I'll bring Italy to us. Tell gramps I said hello."
He finished his drink. He was thinking on how to free Meg. Ruby told him she was sleeping peacefully, but was waiting for her Clarence.