In A Moveable Beast,Freya opens the music box he gifted her prior to the wedding and she is pulled into a vision where she sees Killian. He collapses after Freya discovers blood on her hand from the back of his head. Wendy deals the tarot cards for Freya, revealing that his boat had been destroyed in a storm but he was on dry land. The cards cryptically show that he is taking a lot of money from people but his exact method is unknown. The rest of Killian's fate is shrouded from the cards by the spirit animal of an owl. Killian is later revealed to be in Santo Domingo, where he unknowingly discovering his abilities as a witch. Unintentionally, he is reading the minds the people at the tables where he has been gambling, winning large amounts of chips. A woman called Eva comes into his room and is revealed as the one who had saved him and nursed him back to health. When she asks if he will be returning back to his home, he tells her that there is nothing left for him there. When they kiss, it is revealed that she bears the tattoo of an owl on her lower back.
Later, in The Son Also Rises Freya and Frederick use a spell to astral project and find Killian, successfully. And in the next episode, The Old Man And The Key, Freya arrives into the hotel where he is, and take him back home, along with Eva.
In the episode The Brothers Grimoire, Killian and Dash pratice magic together for the first time. They use their recently acquired The Gardiner Grimoire, that looks like has a lot of dark magic, to cast a spell that they belive to be a Invencibility Spell. These spell actually turns out to be Vitality Spell that sucks the life force from Killian to Dash, causing him to became weak. His skin starts to have burns, his ribs break and he barely has energy to move. With the help of Ingrid, they reverse the spell.
In When A Mandragora Loves A Woman, Eva gives him what is belived to be a love potion. They have sex, and during it Eva casts a Fertility Spell.