YOU SAID:
Man i have had the worse day
INTO JAPANESE
私はもっと悪い日を過ごした男
BACK INTO ENGLISH
I had a worse day man
INTO JAPANESE
私はもっと悪い日の男を持っていた
BACK INTO ENGLISH
I had a man on a worse day
INTO JAPANESE
私はもっと悪い日に男を持っていた
BACK INTO ENGLISH
I had a man on a worse day
That didn't even make that much sense in English.