In the second season, after Madalena and Gareth usurp the throne of Valencia, Richard allies himself with Galavant, who now hopes to rescue Isabella from being forced to marry Prince Harry of Hortensia, her eleven-year-old cousin, against her will. Along the way, Richard attempts to find a new role for himself in life and he falls in love with Roberta Steinglass, a childhood friend. Galavant goes to great lengths to recruit an army to help him on his quest. Richard also draws a sword that, unbeknownst to him, is to be drawn by the “one true king to unite them all.” At the same time, Chester Wormwood, an evil sorcerer who doubles as a wedding planner, attempts to hypnotize Isabella into accepting being married to her cousin. When he fails, he flees from Hortensia to Valencia and encourages Gareth and Madalena to start an unplanned war with Hortensia. Wormwood also offers to teach them his “dark dark evil way” (abbreviated as D’DEW) of sorcery, which Gareth rejects but Madalena secretly accepts. All the episodes of the season lead up to a large battle between four armies, including those of Valencia and Hortensia.