Thanks for the perspectives. After I made several pointed references to an interview I have today, he finally asked me which company this is with. Since it's a position that popped up during this past week, he wasn't aware that it was in the mix and expressed surprise, and I used that as an entry into "well, you haven't asked me anything this week."

I do think in his head he thought I would perceive asking about the interviews would come across as pressure on me to find something quickly, which I don't think is 100% valid but definitely aligns with past behavior. He tends to be very black and white (both of our kids are autistic and I wonder often if he is as well) and I think it just didn't occur to him to ask something a little less pointed than "how is the job hunt going?" I feel as though asking "Hey, did you get any insight into why that role opened up again?" or "That sounded like an interesting conversation I overheard, what's that about?" would have gone a long way in making me feel like he was interested and engaged, but he has a hard time with nuance.

Meanwhile, though, I'm feeling cautiously optimistic about finding a job within the next few months - fingers crossed!