YOU SAID:
your mother is very nice. i think i should date her
INTO JAPANESE
あなたのお母さんはとても素敵です。私は彼女とデートすべきだと思う
BACK INTO ENGLISH
Your mother is very nice. I think I should go out with her.
INTO JAPANESE
あなたのお母さんはとても素敵です。私は彼女と付き合うべきだと思う。
BACK INTO ENGLISH
Your mother is very nice. I think I should go out with her.
That didn't even make that much sense in English.