In Pilot, Freya is having dreams about a mysterious man she has never met before. When Killian arrives at Freya's engagement party, Freya is surprised to see the man from her dreams, and learns that he is the younger brother of Dash Gardiner -- Freya's fiancé.
Despite Freya's commitment to Dash, she and Killian are drawn to each other. Killian even gets a job as a bartender at The Bent Elbow, where Freya works.
In Electric Avenue, Freya is attacked by the ghost of Elyseat the Bent Elbow. Elyse uses her ability to manipulate electricity to scare Freya, she then tries to kill Killian, manipulating the electricity in the bar so that when Killian presses the light switch he is electructed. Fortunately he was rushed into hospital and was saved byhis brother Dash.
In A Parching Imbued, Killian reveals that he is going away, later in the episode he confesses his love for Freya, telling her that if she marries Dash "he will destroy her", Killian asks Freya to run away with him.
In Oh, What A World!, after Killian confesses his love to Freya, he opts not to go to the wedding. Later, Killian leaves a gift for Freya: an old music box. Upon listening to the music box, Freya becomes emotional because she recognizes the song as one Killian played for her. Freya's father, Victor, tells Freya that Killian is really Henry, Freya's soulmate in her past life in the 1900s. Victor tells her to trust her heart, and that Killian may not be the trickster. After the talk, Freya tells Dash that she can't marry him, angering Dash. After Dash and Killian's mother Penelope is killed, the powers she took from her sons are restored. As Killian is about to leave town, an angry Dash charges at him, unleashing a Telekinetic Wave that throws Killian through the air, dropping him onto some stacking crates. Dash unleashes another wave, throwing Killian in the air again, this time landing on his boat, unconscious. Dash then unhooks the boat and pushes Killian out to sea.