Make things better by looking ahead....

[Umbrella24]

What feels like a typical am call -- he calls, I answer brightly, he sounds irked, I feel at a loss for what to say so I ask a question which is always a bad thing -- I still try to sound bright, eventually he warms up (maybe).

OK, here's a glass half-full view. Perhaps he's having a crappy day for whatever reason, and calls you to cheer himself up. This sounds in line with what you described. Sage, don't be so damn negative all the time!