instruction: Is the next sentence syntactically and semantically acceptable?

That Anne was in conversation with Mr Elliott dismayed Captain.

response: acceptable

instruction: Is the next sentence syntactically and semantically acceptable?

I talked to Winston about him.

response: unacceptable

instruction: Is the next sentence syntactically and semantically acceptable?

The luscious chick who Billy went to the movies with will wed me ere the morn.

response: acceptable

instruction: Is the next sentence syntactically and semantically acceptable?

The horse jumped out of the stream.

response:
acceptable