Anakin desires to free his mother and the other slaves on Tatooine and bring good to the galaxy; Elphaba desires to make Oz an equal place for humans and sentient Animals alike. Betrayals by their mentor figures are what prompt both Elphaba and Anakin to turn against the institutions that shaped them: Anakin the Jedi Order and the Republic; Elphaba the corrupt dictatorship of the Wizard.

In the course of their painful journeys, both end up profoundly shaped by a brief - and ultimately bittersweet - romance.

In the musical, Elphaba falls in love with the charming Vinkus prince Fiyero at university, and, though there seem to be hints of a mutual attraction, Elphaba believes her feelings are unrequited. After Elphaba rejects the Wizard, she is on the run, the entire land of Oz - with the exception of Fiyero and his fiancé, Elphaba's former roommate Glinda - believing due to the Wizard's propaganda that she is a wicked witch, a terrorist. A chance reunion with Fiyero rekindles old sparks, prompting Fiyero - now a leader in the Wizard's guard - to turn his back on his station (and fiancé), to run away with Elphaba. The two share a brief blissful time together, knowing their time will be short. Sure enough, Elphaba is lured into a trap trying to save her sister. She is unsuccessful; her sister is killed when a tornado drops Dorothy Gale's house on her, and Fiyero is captured by the Wizard's guards. Elphaba desperately tries every magic spell she knows in attempt to spare Fiyero's life, but believes herself unsuccessful. Now having failed in saving everyone she ever loved, upon losing Fiyero Elphaba vows never to do good again, declaring herself "wicked through and through."

Their romance plays out somewhat differently in the original novel, but Fiyero's fate is still a huge catalyst in Elphaba's transformation. The two meet at university and, while friends, they do not yet appear particularly close. Three years after Elphaba rejects the Wizard and disappears into the Emerald City, Fiyero spots her there, and she immediately rebuffs his attempts to get close to her. Concerned, he refuses to be shut out, and Elphaba gradually warms to the company, and the two embark on a passionate, illicit affair. (Fiyero is unhappily married, his arranged wife and children on the other side of Oz.) Elphaba at this point is a member of a very secretive resistance movement, devoted to bringing down the Wizard's regime. Despite Elphaba's entreatings to keep his distance from her, he refuses to leave. Fiyero is brutally murdered by the Wizard's guard, who were seeking Elphaba. At Fiyero's death, Elphaba becomes mute with grief/guilt and joins a mauntery, where she is catatonic for nearly a year. During this blank period she gives birth to hers and Fiyero's son, though Elphaba herself has no memory of it. After, she removes herself and the boy to the distant Vinkus that was Fiyero's home, losing herself further and further in her sorceries, and fruitlessly seeking forgiveness for her part in Fiyero's death. Eventually, as in the original Oz tale, she encounters Dorothy and is killed when Dorothy tosses a bucket of water on her.

In both book and musical, the ending is bittersweet. In the novel, both lovers die, but their son lives on to continue the story. In the musical, Elphaba fakes her death, and Fiyero does survive, having been transformed into the Scarecrow by Elphaba's earlier attempts to save him. The two are reunited, but since Elphaba will forever be a marked woman, they are forced to live out their days in secret, telling no one of their existence - even Elphaba's beloved Glinda, who mourns the death of the friend who forever changed her.