Crowley noticed Michael glancing over at the empty table but didn't say anything of it, in any case Michael very quickly spoke up and took Crowley's mind off the matter soon enough afterward as it was.
"Might at least keep an eye on them, wouldn't hurt," while he knew he had to put some distance between himself and the Winchesters in order to gain some perspective on his own life and his own possible future in Preya, the possibility was that if he didn't stay in communication with Dean for a time, Dean might become cool towards him, and Dean (and to a somewhat lesser extent Sam) was the only one who seemed to tolerate his presence. Castiel and the others, if they had their say, would send him on a one way ticket back to where he came from, by means of his death most likely.
His money was on the Harvelle girl. How delightful.
"I'm pretty much a bloody hermit so far," he admitted awkwardly, "but I have to say it's nice to get away from everything I left behind, all the bureacracy and the backstabbing. I mean, there are parts of Hell I miss. Can't really get into it with you because I don't think you'd get it, but." He shrugged.
Crowley watched as the bartender refilled his drink, taking another sip afterwards. The admission from Michael came at a surprise, and Crowley looked it, to a certain extent of course. "I'm not here to raise Hell," Crowley told him, "I mean, that whole nightclub thing, I might give that a whirl. But you're not the only one that's not a hundred percent. Being away from Hell... I wouldn't say it's weakening me, but it's not exactly pleasant."
He looked down at himself, then up at Michael. "Rather ironical, we demons spend so long trying to claw our way out of the pit, and now I'm wishing I was back in there."