This is where this episode was frustrating, because when Jack was alone he was obviously feeling remorse and/or guilt about 'the accident' and was afraid to face Sam and Dean, yet when he saw them, he showed no emotion at all. And yet he was so proud, telling them that he was making angels, so he still craves their affection, which as you said, he wouldn't care about if he was soulless! It could tie you in knots.