They already made a companions trailer with bull, Vivienne, Sera and Blackwall. I hope they will do the same with the remaining companions and advisors
My dream is another two (or three?) trailers in the same vein as the "Stand Together" one, for the rest of the companions and advisors, like you say... each voiced by the Inquisitor VAs we haven't heard yet, so we get a good go at hearing them all.
And then another one even more epic than the rest with the narration swapping between VAs as it goes, culminating on one big mass chorus of "....THE INQUISITION!!"
But that's just me.
Anyway, back on topic:
What would you do on a date with Josephine? I would go for an evening by the fire with wine and poetry reading. (cliché, but so what? I like coziness)
I think... a quiet breakfast every morning as she updates the Inquisitor over tea and toast about the upcoming stuff for the day. Actually, that sounds too much like work...
A date? A trip through a huge hedge maze with a picnic at the end of it.