Sentence 1: I've known him slightly on and off for some years, and this morning I ran across him in the street.

Sentence 2: This morning, I saw him outside of the gas station.
Is this second sentence entailed by the first?

Answer: it is not possible to tell

Sentence 1: I'm a friend of Jon's.

Sentence 2: Jon is my best friend.
Is this second sentence entailed by the first?

Answer: it is not possible to tell

Sentence 1: ouch yeah

Sentence 2: No.
Is this second sentence entailed by the first?

Answer:
no