YOU SAID:
Shall I give you despair?
INTO JAPANESE
絶望させましょうか。
BACK INTO ENGLISH
Shall I despair?
INTO JAPANESE
絶望しませんか?
BACK INTO ENGLISH
Would you like to despair?
INTO JAPANESE
絶望しませんか?
BACK INTO ENGLISH
Would you like to despair?
That didn't even make that much sense in English.