YOU SAID:

The man wasn't quite sure if he was in fact a woman or not

INTO JAPANESE

男でしたか、彼が実際に女性かよくわからない

BACK INTO ENGLISH

Whether he was a man, he is actually female or unsure

INTO JAPANESE

彼は男だった、かどうか彼が実際に女性かわからない

BACK INTO ENGLISH

Do not know whether or not he was a man, he is actually female?

INTO JAPANESE

彼は男だったかどうか、彼は実際に女性を知らないか。

BACK INTO ENGLISH

Whether or not he was a man he doesn't know women actually do.

INTO JAPANESE

彼は男だったかどうか女性が実際には彼は知らない。

BACK INTO ENGLISH

Whether or not he was a man he doesn't know in fact women.

INTO JAPANESE

彼は男だったかどうか彼は女性を実際に知っていません。

BACK INTO ENGLISH

Whether or not he was a man he doesn't know in fact women.