You're not the only one who's wondered that. I have, a lot.

[ She's not sure what he means exactly by hurting their brothers and sisters, but she'll ask later. If she tried now she'd probably end up pointing out that they deserved whatever it was, and she's sure Castiel doesn't want to hear that now. ]

Things were much simpler back then, it's true, but it's always worth it Cas. The decisions you've made, bad or good, at least they were yours. Not some absent Fathers supposed orders.