About this image

Ralof: Have you always been that ugly, Gersilla ?
Gersilla: Ripoff, that is a personal question.
Helina ( to Caradhwen ) : If he thinks she is ugly as a girl, he should have seen Gersilla when she was a boy before that magic artifact changed him to her.
Caradhwen: Ah, I wondered why there was a boy with you and your mother in that picture in screenie AIS 043.

Ralof really did ask that question in the game.
Caradhwen is referring to this picture:
AIS 043 - Mother and Children
http://skyrim.nexusmods.com/images/66521