It's still a terrible idea, but he does sort of want Crowley, or someone, to succeed one of these tries. He already knows Crowley is headstrong and not going to be convinced not to go, and hell, maybe flight will even get him there. If he dies, he might come back. If he doesn't return, one less problem for them to deal with.

"Sounds good," he says with a nod, a note of concern in his voice. "If you make it, at least do one thing? Don't kill Robin. I'm sure you can find plenty of information without resorting to murder."