While preaching in Rovna and Skalitz, he fell in love with his young housemaid, Mary. When she became pregnant, she went back to family's farm, north-east of Skalitz, to live with her mother and father. Simon sent them money as compensation, and to ensure that Mary and their child would be cared for. Sadly, she and the baby died in childbirth.
Father Simon, convinced that their death was a punishment from God for his sin of fornication, fell into a deep depression, eventually leaving his church to seek penance in the nearby forest. He continued to leave comfrey flowers on Mary's grave.
During the quest A Man of the Cloth, Henry is tasked with finding a priest to lead the congregation at St James, and seeks out Father Simon, who is being held captive in the forest, west of Skalitz. After the Tramps are either driven away or talked down, Henry convinces Simon that he is needed back in Rovna.
Later, in the quest In God's Hands, Henry asks Simon for help curing Phillip, who does not seem wounded but is dying. After determining that Phillip was found hiding from the Cumans in a pile of dead bodies, Simon gives you the recipe for Artemisia potion in order to purge Phillip's intestines. If this is completed quickly enough, Phillip will be saved.
- If completing In God's Hands after A Man of the Cloth with Father Francis returned to Rovna the player may not be prompted to the location of Father Simon.