Simon Liana is the son of actress Maria Liana, who bought him a case of expensive wine from Mackey the Merchant when he left home to join the Shepherds. After participating in a Shepherd mob which killed a young Grrrlf, Simon became disillusioned with the cult and left it to become a Child of Henne, confessing all he knew about the Shepherds to High Brother Fellich Marr and hoping to find solace and redemption with the Children.
Originally posted at the Temple of Henne in Durst, Simon enjoyed being stationed so close to the Waste for the dramatic role of that location in many of his mother's performances, and entertained local children by telling them about her role in The Mana of Love. However, some of his former Shepherd associates recognized him and his house was burnt to the ground. To avoid further trouble, High Brother Fellich Marr reassigned Simon to Ravenne, where a new Temple of Henne was being built. Simon buried his Shepherd Medallion in his garden there as a symbol of growth from his former life.
An ambush waits for the party in Ravenne, along with the note that had decoyed Simon to Levosche, purporting to summon him to officiate a wedding. He knows nothing about the ambush and found nobody getting married in Levosche, but accepts the greeting his mother sent with the party and explains his history with the Shepherds. Concerned for their lives, he first refuses to tell them where the Shepherds' headquarters is located, but accepts their reassurances and explains how to find the Shepherd Cave, adding that they are welcome to use his medallion to get inside.
- Referring to Simon's house, Aren remarks that one can always somehow tell where one of the Children lives.
- After the party visits Simon's house, they can meet the enchantress in Levosche.