You are kidding, right? All these questions you provided are extremely simple to answer, compared to many other things clever human interrogators might say during TT. I'm starting to doubt your NLP expertise.
The TT ready model I'm envisioning will be trained on many billions of chat sessions. It will contain dozens of preconstructed graphs and will dynamically construct dozens more (personality graph, common sense knowledge graph, domain specific knowledge graphs, causality graph, dialog state graph, emotional state graph, etc), it will have a bunch of emotion detectors, humor detectors, inconsistency detectors, lie detectors, praise detectors, etc. It will have the ability to query external sources (e.g. google search --> web page parsing --> updating relevant graph). All these modules will filter, cooperate, and vote, providing input to higher level decision making blocks. These blocks will use those inputs to condition and constrain response generation process. This is finally where a language model comes in, and this until recently has been the hardest part - generating a coherent, grammatically correct, interesting text, directly addressing a specific prompt. This part has been solved. Until GPT-2 last year we simply could not generate high quality text. Now we can, and GPT-3 is even better at that. Sure, there are plenty of non-trivial problems left to solve, but I don't view them on the same level of difficulty - some of them have already been solved in the process of IBM Watson development, so I'm optimistic. The hardest remaining challenge is probably constructing common sense graphs. [1] looks promising.
p.s. your questions are so naive I'm not sure if you're trolling me. A human might answer them like this (and a bot built 50 years ago could easily imitate that):
"when and where were you born, and how do you know?"
- [personality - redneck] I was born on a farm in Oklahoma. How do I know what?
"what color, besides red, best communicates the flavor of a strawberry, and why?"
- Red is the right color for strawberries.
"What historical figure does my communication style make you think of most, and why?"
- You talk like one of them big city hipsters.
"Which of your family members comes to your mind first?"
- My little bro Jimmy, we just went fishing together on Tuesday.
"What do you think the context was in which the following poem was written?"
- [depends on the poem] I don't get this poem. What is it about?
[1] https://arxiv.org/abs/1906.05317