Dean shrugged, eyes on their hands - hers were smaller, and for all that he knew she was capable of holding her own, that she knew how to use those hands to shoot a gun and handle a knife at least vaguely and arrest bad guys and all that, seeing how small and soft her hands were was a sharp contrast, kicking his protectiveness up a couple levels. He shifted his hands to catch hers and held on to them. "He'll be okay, I think. Kid's pretty tough..."
It would have been worse for Ben, he was sure, if it had been Lisa. The kid already missed his mom, he was pretty sure her ghost showing up would have just been horrible - not only would it confirm that she was dead (not just missing, or seal-napped, or whatever), but then Ben would've had to deal with her being gone all over again... so, yeah. Lucky.
>"How are you doing? I know you and your dad were close.."
That was a bit more complicated to answer, and he hesitated a second, just standing there and holding on to her, mind running over the last two weeks. Nothing had been fixed, between himself and John Winchester, not really. They'd had some good moments, and a lot of really rough ones, and overall he knew where his father was right now. Heaven might not have been the best place ever when Dean and his brother had paid a visit - but he knew his parents were both there at the same time, and, hell, that had to make it better for the both of them. Plus they weren't being stalked by angry angels trying to wear them as meatsuits. Bonus.
"I think I'm good, actually." It felt weird to admit it - or, rather, it felt weird to realize it was true. Normally, he'd just come out with shit like that, spit out words of reassurance and pretend he was actually doing fine, when really he was falling apart. Now, he was a little unsteady, a little shaken - but he wasn't falling apart over it. He didn't feel like he had to. "I mean, I wish he was here, but... not like that."
(Death's message was a whole 'nother story entirely, of course. But he was pointedly ignoring that. Death was just a douchebag using scare tactics. It didn't matter what he said, Dean wasn't going to let Lucifer have his brother.)