The two did not know one another prior to the beginning of the RCC's campaign against Stanley. Although they knew each other for only a brief time, and were superficially very different, the deeper similarities which came from them both being Royal allowed them to develop a strong romantic relationship. Ansom was hesitant to embrace his love for Jillian until learning she was actually a princess whose kingdom had been destroyed. Despite his hesitations, Ansom continually trusted Jillian despite large amounts of evidence pointing to her being a traitor. The love that Jillian and Ansom shared gave Jillian the strength and desire to break Wanda's suggestion spell.
Jillian was deeply troubled by the death of Ansom at the Battle of Gobwin Knob. After learning that Ansom still lived as a decrypted unit, Jillian formulated her own plan in contradiction with Don King, her close ally and the Ruler of Transylvito, and in contradiction with her agreement with Charlie, in order to save Ansom. When they first met following Ansom's decryption and conversion to Stanley's side, Jillian ordered Vanna the Turnamancer to try and turn him. When this attempt failed, she took Ansom prisoner, abandoning her allies and leaving Wanda behind once again.