Quite a few moments, but off the top of my head:
In the final episode of season 2, Treguard says:
Ah, how pleasant! I should relax here if I were you team, there's absolutely no danger - and as an added bonus a small friendly, furry creature is about to come and pet you.
In the first episode of season 8, the look on Treguard's face as he suddenly notices Richard's height and looks really quite surprised and awkward.
There was a moment in one of the middling seasons where a dungeoneer was turned into an goblin. Treguard tried to explain the possibly bad predicament he was in, but Chris just came right out and decided, in a squeaky voice, that he wanted to stay a goblin! Treguard admitted that's one way of looking at it
The entirety of Barry's quest in season 7 is also hilarious pretty much throughout due to the fact that our dungeoneer seems to do everything entirely by himself and has got quite a way with words. If only all dungeoneers were like him