My brain got broken (possibly permanently) at work this afternoon.
Male Coworker (MC) sent out an email saying he was going to be out Monday and possibly Tuesday. Annoying Coworker (AC) asked why and he said his grandmother had died. The rest of us said, "Oh, that's too bad. I'm sorry to hear that" types of phrases. AC said, "oh that's too bad", paused for a moment and then said, "Was she very old then?"

MC said, "Yeah, she was kind of old, she's had Alzheimer's for awhile". AC said, "Oh, well it was for the best, if she had
that".
*pause*
AC brightly says, "So how old are your parents?". MC sounds kind of stunned, but answers. AC continues to grill MC about his parents, any siblings he has, any siblings his parents have, who will be at the funeral, does he know who the executor of the estate is, and on and on and on. Most of us by the end were just sitting with dropped jaws! MC finally got away by just standing up and leaving. AC works for an additional hour beyond when MC leaves, so couldn't follow him out, but looked very disappointed that her inquisition had to end.
Now I know who not to answer questions from in the future! And seriously, who thinks it's okay to grill someone about their family when they've just told you a family member has died?