Varis
First Post
There's some good advice here.I can't really quantize it, it's an art. But let's try anyway.
1. How much awesome should you bring? As much as you can. You, as a player or DM, are entertaining the rest of the table with your contributions. Do it.
2. Where should you bring it? Everywhere.
3. How do I expect you to bring it? First, I expect you to know the tastes of your fellow players. I expect you to know what's cool, what's lame, and what crosses the line into bad taste.
So, keep in mind what you want to do and the tastes of the other players.
Then play your character agressively, driving towards his goals. This might create internal conflict, and if it does, show us. The same goes for the DM, playing his NPCs. These NPCs should be created with an eye towards challenging/opposing the PC's goals.
4. How do you make each die roll count? It's simple. It changes the situation. If it's a success, it changes things in favour of the PCs. If it's a failure, it makes things harder for them.
How's that?
On Sunday I managed for the first time, to complete 2 seperate skill challenges AND make it fun.
In addition to Lost Soul's advice, I also conducted the skill challenge without announcing it.
The PC's simply thought they were role playing, and in the course of doing so, tried to influence a powerful NPC.
In the course of their efforts, I'd ask for a diplomacy or bluff check to 'influence' my reactions,...I set the DC in my mind and quietly counted the number of successes v's failures. When players wanted to 'assist' in a diplomacy check for example, I'd ask them to 'say' what their characters were saying (and apply negatives or bonuses as appropriate).
It was all done as a natural, organic evolvement of the roleplaying experience.
I was able to replicate this a bit later in a 'torture' scene (yes, alignment issues will be in my next post

So there you go,..I might be just a matter of not overthinking it, relaxing and allowing it to evolve through the course of roleplaying.