YOU SAID:

In my junior year of high school, this guy asked me on a date

INTO JAPANESE

私の中学1年生の時に、この男は私にデートをした

BACK INTO ENGLISH

At the time of my junior high school first grader, this guy ran a date for me

INTO JAPANESE

私の中学1年生の時に、この男は私のためにデートを走りました

BACK INTO ENGLISH

At the time of my junior high school first grader, this guy ran a date for me