I'm not exactly 'new' since I've had five characters so far and learnt a lot, but I've never actually been able to communicate with any of the NPC's by using 'ask', especially rthe ones guarding doors that I want to know what's through them, or people like the bankers and lenders.
"ask" isn't usually the keyword.
You'll want to try "discuss <npc> topics" or "discuss <npc> name" to get them going. "talk <npc> topics" (& etc) also works.
Keep in mind that not every npc has been programmed with a talk script so you may still run into instances where you can't talk to one. Bartenders are a good bet, though.
Ah thank you, I got a little frustrated with it haha. Especially with these people guarding interesting entrances and just looking at me blankly as I try and communicate with them.