Sentence 1: 'I can't imagine what you mean,' I deadpanned.

Sentence 2: He made no sense at all in his speech.
Is this second sentence entailed by the first?

Answer: it is not possible to tell

Sentence 1: It was a nice park; peaceful and green, possibly more so than anywhere else in the city.

Sentence 2: The park was serene and beautiful, despite the dirtiness of the rest of the city.
Is this second sentence entailed by the first?

Answer: it is not possible to tell

Sentence 1: All you need to do is just wander off the beaten path, beyond the bustling tourist zone.

Sentence 2: There is no point going off the beaten path, there is nothing there.
Is this second sentence entailed by the first?

Answer:
no