It might help just to see these people as folks who hate the job as much as you hate them doing the job. I don't know, but I suspect they have to ask these questions or they get fired. They have no choice. They'd much rather look at the screen and pass on the 'De Ja Vu' experience, but they can't.
It reminds me of the time I asked tenants in our little house in Wales whether they were still employed. It wasn't me being an arse. It was a question on the insurance, and I hadn't checked in 5 years - I'm supposed to check every year. I had to ask the letting agent three times, eventually explaining that I personally couldn't care less if they're employed - it's just that if they're not, we need to get different insurance, so if the house burns down, it's still insured.
Eventually, they begrudgingly passed on far too much information. All I wanted was a yes/no... but I ended up with details of both employments.
I haven't dared ask since.
Sometimes, we all just have to go through the motions of asking questions we'd rather not. I just hope that if the house burns down, we're insured. I'm pretty sure he's working. We've since heard she's at college.