Short version: I helped Triss, made a compliment and acknowledged it and kissed her and asked her what should come next. The problem: the quest does not trigger now or never, is it because I'm still running the quest: the most wanted woman in Redania? I have a second account on the Xbox where I did it exactly like the current account and it worked there…
Did I understand you correctly? You have completed "Matter of Life and Death" - the party in Vegelbud Park.
Did you already go to Triss afterwards (!)? Only when you visit her again in her house does she ask you for help - which then amounts to the start of "Now or Never". It does not start automatically, but only through the appropriate dialog.
The fact that "Redanias most wanted" is still going shouldn't really interfere in this direction. The problem is rather the other way around, that afterwards you can't show or give Triss the crystal from the megascope that you find during this quest.
