User blog comment:Crystaline09/Old Painter in "Kept Waiting For A Response"/@comment-6986530-20130526220509

Well, Kyle could have met Rilliane again any number of ways before the events of this song--he already knew that Allen took her place on the Guillotine. He wouldn't have told anyone for the reason that he let Allen die--if people knew the Daughter of Evil was still alive it might cause rioting from those who want revenge on her. (He wouldn't need to tell Germaine anyway; she'd already met and forgiven Rilliane in one of the later novels.)

For the last one, he could just be guessing or he was told at whatever point he met Rilliane again.