Anna's first instinct was not to go to her brother. He would take some persuading, even if he wasn't so fond of the "mud monkeys" as he called them.
No, she wouldn't go to Uriel until her other options were exhausted -- not that she had many. She would seek the help of a demon.
"Ruby," she hissed, catching the dark-haired woman's attention. The timeline was uncertain, but she was with Sam now. This would require some convincing.
"Anna?" So clearly it was after they met. "What are you doing here?"
"Shh," she said, nodding at the sleeping Winchester, and holding a finger up to her lips.
Anna waited in the hotel's dimly lit hallway for Ruby to slip on an oversized t-shirt and follow her out. Not only was it poorly lit but also poorly heated, and Ruby shivered as she shut the door behind her. She faced Anna, pulling at her sleeves and hugging herself tightly.
"Ruby, I need to ask you something very important."
Ruby's eyes snapped up, suddenly rapt with attention -- as though just having an angel crop up out of nowhere wasn't enough for this demon; she needed to be told of the gravitas of her situation to really feel it.
"Why are you helping Sam Winchester?"
Ruby shook her head, sniggering wryly. "What's it to you? I have my reasons."
This was going to be more difficult than Anna thought. She would have to go in strong.
"What would you say if I told you I could stop the Apocalypse?"
Ruby's eyes widened. This wasn't what she had been expecting. "How?" she said, half laughing in disbelief. "You can't. It's going to happen."
If Anna were capable of reading the demon's mind, she would have done so at that moment. An attempt could leave her grace scarred and burned, and Anna knew this -- if she didn't need every last ounce of power to accomplish her goals, she would have done it in an instant.
"Why are you so certain?" she asked, and the question felt feeble even as it came out of her mouth.
To her surprise, Ruby grinned at her.
"Because I'm gonna make it happen." She spoke through her teeth.
Anna was beginning to think this was a lost cause, after all. She'd have to change her tactics.
"If you come with me, you can be free of all this. I'll protect you from Hell." Ruby was listening now. "Whoever it is whose thumb you're under, I can get you out."
Ruby's eyes glinted, not quite demon-black, but dark, shadows dancing in the corners. If Anna chose to she could see Ruby in her true form, but she thought she liked her better this way -- in human form, which was, Anna suspected, the way Ruby often saw herself.
"How?" Ruby asked, voice low. "What's the catch?"
This was the hard part. Anna let out a slow breath.
"You have to help me kill Sam Winchester."
Ruby faltered at this.
"You think that's all you have to do? You think you can just stop it like that?"
"Yes," Anna said, firm, standing with her back straight; the stance of a soldier.
Ruby chuckled, but there was a bitterness to the sound. "Kill Sam Winchester. Now there's a plan. Why didn't I think of that?"
"But now you have the force of Heaven behind you."
"No, I don't," said Ruby, catching the angel's gaze and not faltering this time, not looking away or even blinking. She zeroed in on the redhead, staring intently at her as though her demon eyes possessed X-Ray vision. "You don't either."
Anna closed her eyes. She could find no way around it. "Fine," she said, finally looking back up at the demon. "I will find another way."
"Good luck with that," Ruby said, turning away from Anna, her fingers curled around the handle of the door to Sam's room. "Right now, I'm having way too much fun with Sam to just let you off him. Not to mention, it'd put quite a damper on my plans."
Anna breathed a sigh. "Perhaps I'll see you around, then."
Ruby shut the door behind her, but peeked out to give Anna one last toothy grin. "Yeah," she said, "Perhaps you will."