YOU SAID:

Will you go on a date with my friend?

INTO JAPANESE

私の友人とデートに行きます?

BACK INTO ENGLISH

And my friends go out on a date?

INTO JAPANESE

友達がデートに出かけるか。

BACK INTO ENGLISH

Friends go out on a date?

INTO JAPANESE

友人は、日付に出かける?

BACK INTO ENGLISH

Friends go out on a date?