Sam drank in short sips as he listened to Dean, his lips turning up in a smile as Dean mentioned singing. Was there dancing? While he was kind of familiar with the play, a lot of people were, he had never been to Broadway to see it. He didn't know exactly how the characters would act... or if they would dance as they sang - in which case he was definitely going to be there, even if he had to come from his deathbed - but he knew the Grimm brother's works, and he knew Into the Woods was inspired by their stuff.
"So you've got the singing stuff down, dancing too?" He cleared his throat and continued. "And you only have issues with this one part that you have to speak." He set his beer down on the top of the closed ice chest. "Okay, so you probably just wanna bounce lines off of me until you're less wooden, but, Charming - might have been more than just a selfish bastard. He's really handsome, probably the most desired prince in the land, and he knows it, so he's arrogant. And a douche. So he probably just assumes Cinderella will want his protection because he's a typical alpha male, he probably doesn't know strong women exist. I know it's going to be hard to pretend to be handsome," he teased, "but that's the kind of leap you might have to make."