YOU SAID:
he gave me insight on how awkward he is.
INTO JAPANESE
彼は私に彼がどれだけ気まずいかについての洞察を与えてくれた。
BACK INTO ENGLISH
He gave me an insight into how awkward he was.
INTO JAPANESE
彼は私に彼がどれだけ気まずかったかを洞察してくれた。
BACK INTO ENGLISH
He gave me an insight into how awkward he was.
That didn't even make that much sense in English.