Too Much Information Or Maybe Not Enough? from hairylarry's blog

Some D&D players meet a stranger on the road and start into talking and just blurt it all out. I mean, "He seems nice enough." is not a good excuse for giving him too much information. Obviously your antagonist, The Boss Of The Big Bad, is going to pick someone with high charisma to weasel your party's secrets out of your big mouth.

Too Open!

But then there are other players who just never get to the point. They're trying to start a conversation, or talk about the weather, or listen at the next table over when a simple question would likely get the information they need and not really have a dangerous downside even if they are asking the enemies spies. (Except they might lie to you.)

Overly cautious!

But ... asking a question is in fact giving information and it is possible to give something away or be killed just by asking the wrong question in the wrong company.

Now here's where we get all meta and start looking at the same thing from two different points of view.

As a player you want to be careful what you say around strangers. Loose Lips sink ships. But you also shouldn't be afraid to ask anyone a question, ever. I mean that's why DMs have NPCs so they can get on with the exposition.

So this is a strategic decision about game play. Finishing the quest and staying alive.

And when you can't make up your mind? Is this real dangerous or is this maybe just a little dangerous?

Look to your player character. Ask yourself what your character would do. Is he timid or is he brave? Is he drunk or is he sober? Is he smart or is he an idiot?

Let your player character be your guide. Play your role and act it out and the hell with the rest of the party for griping about how you are always getting them into fights.