You didn’t tell us when he asks if everything is OK. That is a large omission, and I hope you can update the original post with examples of what led up to the question being asked. Also, what is the setup there? Are you working at Subway making sandwiches? Do you have adjacent desks? Do you show up to work with black eyes? We are left wondering what’s up.
Certainly anyone who repeatedly asks “Are you OK?” is exacerbating some issue, but I would be hesitant to offer any advice about what you ought to do without reading more details.
(In other words, the missing missing reasons applies here just as it did in the original scenario, for those who remember it.)
Raising questions? No. The only question is how far, how much, how many people will die.