The former (booking a table) is much more "constrained", as in the conversation would most likely not go into much of a tangent, because there are only so many responses to a statement like "book a table for four at 8pm" (8pm is full, 8pm works, etc).
Whereas asking someone how their day was would give the "victim" a much bigger breadth of responses (and additional questions!) that would cause the AI to stumble and fail to give a satisfactory answer. That, and running this 1,000 times simultaneously so that no one person would be able to intervene to "help" the AI would just be a highly unscalable operation.
So yes, huge difference.