Smiley says:
(Asking clarify questions to help)
You are in a Sylvian speaking village.
You talk to the guard and your roll passes to know Sylvian.
You walk pass The guard and talk to the shopkeep. Do you roll again?
If I talk to the guard hours later do I need to roll again?
If you are in this village for a few days do you roll once per day or once per conversation?
I am guessing this is all based on your opinion at the time and whatever is needed to keep the game simple and not drowning in rolls.
I am completely ok with that. Just clarifying questions to ease my mind.
Great questions — I really appreciate you checking in to get clarity.
The short answer is: it depends on the situation. What really matters isn't what you're doing (like speaking Sylvan), but why you're doing it — and whether there's uncertainty, risk, or an interesting consequence tied to the outcome.
You don’t roll just to "understand Sylvan." You roll because you’re trying to do something interesting or uncertain — like convincing a guard to let you through a restricted gate, or eavesdropping on a tense conversation in a language you only half-understand. In those cases, language becomes part of the obstacle that might complicate your success or raise the stakes. It’s not the language itself that’s risky — it’s the situation.
So, if you’ve already rolled once to get the gist of Sylvan and you're just chatting with the shopkeeper later, you likely wouldn’t roll again. But if hours later you’re interrogating a suspect in Sylvan and you need precise meaning under pressure, I might call for a new roll — or maybe give you Disadvantage if it’s a tricky dialect, or Advantage if you’ve already been immersed for a while and the stakes are lower.
The goal is not to bog things down with unnecessary rolls. The dice hit the table when the outcome matters, and both success and failure would push the story forward in an interesting way.
So don’t worry too much about how many times to roll for a language — just focus on what your character is trying to do, and we’ll handle when a Test is needed. I'm always happy to explain why a roll is (or isn’t) called for in the moment.
Hope that helps!