instruction: Is the next sentence syntactically and semantically acceptable?

He is proud of his son's passing the bar exam.

response: acceptable

instruction: Is the next sentence syntactically and semantically acceptable?

I went out with a girl who it pleased that John showed up.

response: acceptable

instruction: Is the next sentence syntactically and semantically acceptable?

You kicked you

response: unacceptable

instruction: Is the next sentence syntactically and semantically acceptable?

Perhaps Gilgamesh should be leaving

response:
acceptable