Nope, he's 100% correct, the first choice you make determine wether Emily and John go on a date, if you give her the all clear they go on this date.
The second choice, when Emily and Melissa are talking to each other in the backyard, determines wether you get to see how the date played out or not.
But at this point the date already happened, it's simply Emily's narration/recollection.
In this most recent update wether you watched the date play out or not, both Emily and John tell the MC that they went on a date.
Don't worry you were correct before.