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Well, I only just started running ROTR recently, and all but one member of my group are totally new to tabletop roleplaying, but the few standout moments of silliness so far would be:
1. The party enter Eryliums chamber and she's already invisible, and the barbarian looks around the room and immediately decides to dive into the Runewell...
2. The party come to the rickety bridge. the rogue decides that she should go first, alone, to check it is safe. The party agree. Then the paladin says "wait, i'll come too, just in case." Fair enough, but just two of us. And then they just all walked onto the bridge at the same time...
It broke, they all held on except the Shaman, who hit the water and ended up at 0 hp. the rogue jumped to pull her out of the sea, to get pounced on by the bunyip. Then the other two decide to try and climb down the cliff to help, before realising that neither of them have climb... so they ended up down there much quicker than they expected.
Finally, the Druid Feather Falls down, saves their asses with a Flame Blade critical, and they drag their sorry selves back to Sandpoint. The goblins were laughing so hard that several of them rolled off the edge of the cliff themselves! At least it was a good excuse for the goblins to not be worried about them coming back XD
3. Beating the snot out of Orik in Thistletop, letting him live, then healing him and paying him 200G to help them out in stopping Nualia. They get to her room, he gets 2 max damage crits with his sword and shield bash (not how he's supposed to fight i know, but i was trying to weaken him a bit since the party was big enough already) and basically killed her in one round. They then went back to Sandpoint and carried on with their business, and it wasnt until 2 hours had passed that suddenly one of them went "Wait, where's Orik?"