YOU SAID:

Would you go with me on a date

INTO JAPANESE

日に私と一緒に行くかと思います

BACK INTO ENGLISH

On the day you would go out with me?

INTO JAPANESE

日にあなたは私と一緒に行くだろう?

BACK INTO ENGLISH

On the day would you go with me?

INTO JAPANESE

日に私と一緒に行くだろうか。

BACK INTO ENGLISH

On the day you will go with me.

INTO JAPANESE

当日は、私と一緒に行くでしょう。

BACK INTO ENGLISH

Go with me on that day.

INTO JAPANESE

その日に私と一緒に行きます。

BACK INTO ENGLISH

Go with me on that day.