Ask someone about something the first time...

Authoring Inform 7
1

I cannot get the syntax right! What am I doing?

Instead of asking the Silver-haired Woman about "something/somethings" for the first time: say "this stuff".
2

Instead of asking the silverhaired woman about foo:
say “[one of]‘I’ll only say this once!’[or]‘You missed it the first time? Sorry.’[stopping]”

3

Isn’t that a bug?
Both

Instead of asking the Silver-haired Woman about "something/somethings": say "this stuff". and

Instead of asking the Silver-haired Woman about "somethings" for the first time: say "this stuff". work as expected, but

Instead of asking the Silver-haired Woman about "something/somethings" for the first time: say "this stuff". doesn’t.

Anyway, you can try

Understand "something/somethings" as "[some]". Instead of asking the Silver-haired Woman about "[some]" for the first time: say "this stuff".
That seems to do what you want.

4 
Test me with "ask silver-haired woman about something / somethings".

I’m pretty sure this bug is on Mantis somewhere… Ah yes. Here.