YOU SAID:

He's head over heels.

INTO JAPANESE

彼はかかとの上に頭です。

BACK INTO ENGLISH

He is head over heels.

INTO JAPANESE

彼はかかとを頭で支えている。

BACK INTO ENGLISH

He supports his heel with his head.

INTO JAPANESE

彼は頭を使ってかかとを支えています。

BACK INTO ENGLISH

He supports his heel with his head.