That awkward moment when a NPC refers to "Ysmir's Beard" and you are playing a female dragonborn.
"but... I don't have a beard!"
Because you know... the Greybeards give you the title Ysmir or something like that.
That awkward moment when you think you have made a clever joke only to realize you might not know what you are talking about.
...you press the wrong button and accidentally wing a prized Daedric artifact behind Belethor's counter. Belethor only smiles and sneers "One person's trash is another person's treasure. Don't be surprised if you find that gone." Needless to say, you do a flying leap over the counter, tackle the sleazeball and snatch it back up as quickly as you dropped it.