YOU SAID:
he would give you the shirt off his back
INTO JAPANESE
彼はあなたに背中のシャツを脱がせてくれるだろう
BACK INTO ENGLISH
he'll let you take off his shirt on his back
INTO JAPANESE
彼はあなたに背中のシャツを脱がせてくれるでしょう
BACK INTO ENGLISH
he'll let you take off his shirt on his back
You should move to Japan!