YOU SAID:
how has your younger annoying sister been
INTO JAPANESE
あなたの厄介な妹はどうでしたか?
BACK INTO ENGLISH
How was your nasty sister?
INTO JAPANESE
あなたの厄介な姉妹はどうでしたか?
BACK INTO ENGLISH
How was your nasty sister?
That didn't even make that much sense in English.