Our best two moments came back to back from our summoner who sometimes struggles with RP.
I just knew there would be trouble when Shayliss targeted him. He was all too happy when he realized there were no rats in the basement and summoned his eidolon (giant slime worm) to join in the festivities.
Fortunately he heard Ven coming down the stairs and when he walks in, stands over the bed, waves his arms, dismisses the eidolon and goes, "whew, glad we took care of that! Let me know if you have any more problems!" I made him roll a bluff check and he dropped a nat 20 on the table. It was amazing.
He then goes to the hagfish to celebrate and rolls a nat 1 on the challenge. Hero to zero in about 5 minutes .