Castiel was used to people not wanting to talk about anything. He himself had taken on the habit of not wanting to talk, thanks to being taught how to 'human' in the Family Winchester. He really needed some better role-models. So he wouldn't have been concerned with Jay not wanting to talk about something. Especially if he'd just outright said he didn't. The angel was surprisingly accepting. Mostly because he could sense deception. He would rather be told someone didn't want to talk, than be lied to.
"I appreciate you being clear." He needed that sort of direction, obviously. "And you're certainly right about that. I'm several billion years too old for you." That was pointedly spoken, his eyebrows raising just a little as if that would make things more clear between them. Not that either one of them needed the dividing line, Cas wasn't quite sure what a date entailed, but he'd trusted Jason enough to think that the 'date' he'd sarcastically suggested they were on, would be something entirely acceptable. He simply hadn't realized.
Jay really had no clue about angels, did he? That was fine, Dean and Sam had needed to learn the hard way, too. He wouldn't order food because he didn't need to eat. The human across from him, however, did need to eat. They'd get to that.
"Three." He repeated as he added absolutely nothing to his coffee. He took it just like Dean did. Why? Because he learned most of his human-mimicking skills from the surly hunter.
He really needed a new role-model.
"Do you ever find that your siblings can be.. overwhelming? Yet, as soon as they're gone, you miss having them there?" Especially with four siblings. He imagined Jason might know exactly that feeling.