Ruby walked out to the back porch of the house they were squatting in. Dean sat on the bottom step, leaning against the banister as the last sliver of sun dropped below the horizon. An empty bottle of whiskey dangled between his fingers.
"Now's not a great time, Ruby," he muttered, voice thick but words not yet slurred.
The wood creaked beneath her feet as she walked to the edge of the porch and set a full bottle of Jack on the second stair. Dean turned, meeting Ruby's eyes so briefly that she almost missed it, and started in on bottle number two.
"Doesn't liquoring me up make you more nervous?" He asked, using his thumb to wipe away a small drop of liquor that had escaped his mouth.
Ruby wasn't sure if he wanted her to feign innocence, if he'd planned this conversation out in his head, if she had an assigned role. But innocent wasn't her strong suit. Hadn't been for centuries.
"If you were going to tell Sam, you would've done it already."
Dean smiled bitterly and shook his head. "You think you know me so well?"
"Didn't you get to know the people you ripped apart in the pit?" She braced herself as the words passed her lips; they came out quickly, before she'd even taken the time to consider what this conversation might mean in the long run. He didn't answer, just took another drink and fixed his gaze on some faraway point.
Ruby sat down on the top step and watched as Dean reeled himself back in and set the bottle next to her boot. She drank deeply, enjoying the warm burn.
"You never hesitated." Dean started, the slur creeping into his voice. "But I don't know why I thought you would."
Ruby raised her eyebrows, the expression probably lost in the rapidly waning daylight, and took another swig. "Torturing you was all the convincing Lilith needed."