"Your compass?" Cas didn't know if it was a metaphysical compass or an actual device but, if it did what it sounded like it did, he knew it would be conflicted in his hands too. Far more than he was.
"More than meets the eye huh? Guess he has a mighty problem. Don't really know what advice would help. I presume all the ladies are interested too? Yeah? I mean, if they weren't then there isn't a problem, right?" It felt good to focus on someone else's romantic concerns. Anything to distract him from his powerful doubt.
"You got it," he said happily as he filled Jack's glass. "Try it without the rum first... for my amusement?"