YOU SAID:
since when was that fun my guy?
INTO JAPANESE
いつから私の男は楽しかったですか？
BACK INTO ENGLISH
Since when did my guy have fun?
INTO JAPANESE
私の男はいつから楽しんだのですか？
BACK INTO ENGLISH
When did my guy enjoy it?
INTO JAPANESE
私の男はいつそれを楽しんだのですか？
BACK INTO ENGLISH
When did my guy enjoy it?
That didn't even make that much sense in English.
