Crowley watched her approach, with a glass of scotch in his hand and a smirk on his face. Really, she was very good. Exceptional even, and as per usual he took a moment to sulk that she hadn't been one of his. Which potentially could have been a good thing, he remembered all too well how he had risen to power himself, but still. If all that devotion she had once had for Azazel could have been for him, oh the pair they could have made.
But regrets were for other beings, not him. He was far more entertained by the here and now, and watching his friend outwit every task he put for her. Even some of the more challenging ones that had foiled a couple of the demons in his employ. (Demons who were, of course, now nicely out of the way. The really good help he tried to keep away from the Winchesters as much as possible.)
The pout made him laugh, a genuine sound of amusement, and with a flick of his fingers the door swung open. He was already standing, pouring another glass of scotch for her. The most expensive drink, from a crystal decanter. He was a demon who liked his luxury.
The drink ready for her, held out, his own in his other hand, he smirked that was as close as he got to an actual smile. "Hello, love."