His jovial expression immediately switched in favor of a more concerned one. As someone who never experienced true, true tragedy in his life (save for his bad schooling experiences, but there are worse things that can happen in one life), Jack always felt incredibly sympathetic for those who had, as well as a bit awkward. How do you exactly react to hearing this sort of news when you've never been in that position?
Nonetheless, he said, "I'm so sorry," biting his lip. He thought briefly, feeling as uncomfortable as his previous self would in an everyday situation, before adding, "Hopefully Chicago has been good to you so far, though."
In retrospect, Jack felt, it was an awful addition and probably one that didn't need to be said, but what can he say? He's never been too good at interpersonal affairs. He's just getting used to it all.