How's it going with your date

[Silverobama]

My friend Kris knew a woman last month; his father set them up and hoped they could make a couple. Kris told me this last month.

And after a month I want to know if they are a couple now. I asked Kris:

How's it going with your date?

Is my italic sentence natural?

 

[emsr2d2]

My friend Kris knew met a woman last month; his father set them up and hoped they could make a couple. Kris told me this last month. And after A month later, I want to know if they are now a couple. now. I asked Kris:

How's it going with your date?

Is my italic sentence natural?

It's natural in a completely different context. That question would be asked while someone is actually out on a date, perhaps by text or WhatsApp. That's not the case here. You'd ask something like "How's it going with that woman your dad set you up with? [Is romance in the air?]"

 

[Skrej]

Since the date is long past - "How did it go on your date?", assuming you haven't spoken to Kris about it since the date occurred.

 

[emsr2d2]

I think some of the confusion here stems from the fact that the OP seems to be trying to use "date" to refer to the woman. That doesn't work in this context/situation. It would work if you were out on a date with her, and someone said to you "Who's that lady you're with?" You could reply to that with "That's my date - Helen". That makes it clear that you are currently on a date with her but it doesn't suggest anything more long-term than that at this stage.