Castiel immediately nodded, feeling guilty for dragging her out into the rain. "Of course," he said, starting to walk in that direction. In retrospect, it would probably have been better to meet at the Ice Room, rather than outside where she could get wet. Glancing at Joanna again, Castiel removed his trenchcoat and draped it over her shoulders, to protect her from some of the rain. Something about Joanna, perhaps simply because of the manner of her death...and the very fact that she had been dead, inspired protective feelings in him.
He had no strong feelings about the Ice Room, though he would readily admit that it did not much resemble the places Dean frequented. His charge would likely have seemed out of place somewhere like this, and Joanna did as well. But there was alcohol and company and a notable lack of rain and cold. And those were the things that mattered to him.
When she asked him about the whiskey, his thoughts went to that night before Carthage and he felt a stab of all too human pain. He had missed Jo, and still missed Ellen, and his failures still pained him. "Yes," he said after a moment's silence. "I do." He lapsed into silence for a short while, and then spoke again. "I'm losing my faith," he admitted.