Crowley, well he didn't as much as stare at Michael as much as just watched him. There had been a reason he'd struck up the initial conversation with him when he'd arrived in Preya, it had been mostly curiosity, but on top of that Crowley felt like they were in a sense kindred spirits, in that they had both been used on multiple occasions, and then shoved to the side and forgotten when they weren't needed anymore. Crowley remembered how after the botched third trial he had been locked up in the Winchesters' dungeon for, well it was months most likely.
He never liked to think about that time, never liked to think about what the human blood did to him, never liked to think about the fact that it was the most vulnerable he'd ever felt in his entire life, even counting the time he was a human, and even counting the time when Casifer had him in his clutches. So many times Dean would go down to the dungeon and punch him until he was a bloody and unconscious mess, and when Crowley woke up Kevin would be there again to start it up all over again. It was only by miracle that Crowley got out of there and he knew it. If circumstances were different, if Abaddon wasn't a problem, the Winchesters would have either kept him down there or killed him.
It was something he'd contemplated since he'd gotten back, the way he'd been treated on his last day on the world he left behind. He got to the bunker with the intent to help, got punched in the face, stabbed in the hand and nearly killed. And then he went ahead and gave his life for them. It wasn't a sacrifice as much as suicide.
Hell, Crowley wasn't even sure that the whole 'mysterious ticket to another land filled with promise of a new beginning' that he got shortly before his sacrifice was the real deal, so when he jabbed the knife into his stomach he knew there was a strong likelihood that he was throwing everything away. But it would be worth it because he would be finally free. Free of the worthless feeling, the pathetic feelings and sentimentality that clung to him. The Winchesters could take their family business and shove it, Crowley was ready for the next chapter.
When he'd woken in Preya, it'd been to relief, but he'd been furious when he'd seen Dean there. And Castiel. Together. Of course he couldn't fucking escape any of it. But Michael was right, he needed to stop kowtowing to them, especially when at the end of the day they collectively didn't give a toss about him and most likely wouldn't mourn him if he was the next one to disappear.
"I didn't really help there," Crowley shrugged, "I'm naturally antagonistic. We got off to a rocky start but well, we're on equal-ish footing now." He smiled at Michael, having another sip of his drink which he'd forgotten about. He hadn't realised he'd actually stopped 'just watching' him a few moments ago and had started staring at him at some point but really, he was still just deep in thought.
"I've met all four of you now," Crowley commented idly, looking down at his glass and swirling it slightly.