Sounds like they're starting the behavioral profiling program there: SPOT. The questions don't have to make sense, they're just supposed to elicit a reaction. Though ones that are so imprecise as to confuse everyone seem unhelpful in this regards.

What was he writing on his clipboard? It's one thing to be questioning people for behavioral profiling purposes (which has its own issues), but quite another to be recording passengers' responses. Should have asked him if he was in compliance with the Privacy Act.