He's being childish. Who has a conversation about the shared qualities of you and your friends in a depressing tone like you're the little Rascals at 30?
OP is right that he should have a 401K and I'm willing to bet the problem goes deeper and they aren't homeowners either. But all he wants to do is talk about how he fits into society. Sure. Fine.
He'll wake up at 33 and realize he should have gotten it together sooner.