Sentence 1: did you stay up late and catch this Red Dwarf oh that was a scream

Sentence 2: I really liked last night's Red Dwarf
Is this second sentence entailed by the first?

Answer: it is not possible to tell

Sentence 1: But Drew was uncertain just how he would rub along with Shannon in the future.

Sentence 2: Drew did not know if he would get along with Shannon.
Is this second sentence entailed by the first?

Answer: yes

Sentence 1: Situated on the route of the ancient caravans that brought goods from the Middle East and Central Asia, the sandstone citadel of Jaisalmer, protected by an imposing double set of bastions, rises like a mirage from the sands of the Thar Desert.

Sentence 2: Many ancient caravans stopped in Jaisalmer for the night before traveling on with their goods.
Is this second sentence entailed by the first?

Answer:
it is not possible to tell