Sentence 1: The first time was the worst.

Sentence 2: It couldn't have been worse than the first time.
Is this second sentence entailed by the first?

Answer: it is not possible to tell

Sentence 1: well i think i'll go see that this weekend or next weekend one or the other

Sentence 2: I'll probably go see it this weekend or next weekend but I might not have the time.
Is this second sentence entailed by the first?

Answer: it is not possible to tell

Sentence 1: um-hum yeah i i think that's um well i think that's an important thing personally um

Sentence 2: In my opinion, that's a very valuable thing
Is this second sentence entailed by the first?

Answer:
yes