Sentence 1: Look at the landscape of his life and you'll see a boneyard.

Sentence 2: An observer can point out that he is living his life to the fullest.
Is this second sentence entailed by the first?

Answer: no

Sentence 1: We're always saying, 'Will it pay?'

Sentence 2: We always wonder if it will provide an income for us.
Is this second sentence entailed by the first?

Answer: yes

Sentence 1: right i did start a college fund i'm not uh i have one again at UT down there now her first year and she's almost gone through her whole college fund you know

Sentence 2: I have no college fund, and I have no college either.
Is this second sentence entailed by the first?

Answer:
no