Jack is a wealthy young revolutionary and author of a scandalous political tract called *The Revolutionist’s Handbook*. He considers himself a forward-thinker who actively flouts social conventions, viewing marriage as a trap that derails philosophical progression and human ambition. Despite his lofty ideals about the working class and socialism, he relies heavily on his practical chauffeur to manage his everyday life.

Roebuck is an affluent older gentleman and long-time family friend of the Whitefields. He views himself as a liberal and progressive thinker, but his rigid adherence to social propriety reveals a deep underlying conservatism. He absolutely despises Jack's radical ideas and initially refuses to share guardianship duties with him.

Octavius is a sweet, overly emotional young artist who holds incredibly romanticized ideals about the world. He devotes himself entirely to pursuing Ann Whitefield, placing her on a pedestal despite direct warnings from his friends about her true nature. He is generous and forgiving, though his intense sentimentalism makes him willingly naive.

Ann is a charming young ingenue who uses her perceived innocence to easily manage the men around her. While she outwardly defers to the wishes of her late father and her new guardians, she quietly orchestrates social situations to achieve exactly what she wants. She is highly pragmatic about marriage and relentless in securing her own future.

Violet is Octavius's pragmatic and resolute sister who cares little for social expectations when they interfere with her goals. She carries a scandalous secret regarding her romantic life and actively orchestrates her financial future, refusing to let idealistic notions of hard work or independence ruin her comfort.

Mrs. Whitefield is Ann and Rhoda's widowed mother. Though she projects the image of a quiet, timid woman who strictly adheres to social convention, she is highly observant. She recognizes her daughter's manipulative nature perfectly and understands exactly how social dynamics operate within her household.

Henry is Jack's highly capable, working-class chauffeur who possesses technical skills his wealthy employer lacks. He is a grounded realist who constantly offsets Jack's lofty philosophical musings with blunt observations, taking great pride in his mechanical expertise and his own social standing.

Hector is a romantic young American who depends entirely on his wealthy father's vast fortune. He holds chivalrous, idealistic views of marriage and desires to assert his independence through hard work, though his grand gestures are quickly shut down by the pragmatic woman he loves.

Hector Sr. is an older, incredibly wealthy man of humble Irish origins who holds a deep grudge against the English upper class. He uses his massive fortune to exert control over his son's life, demanding a socially profitable marriage, but quickly finds himself outmaneuvered by a younger woman who shares his sharp business sense.

Mendoza is a former hotel waiter who now serves as the president of a band of thieves in the Spanish mountains. He robs passing motorists while engaging in eloquent debates about socialism and wealth distribution, yet remains a heartbroken romantic who writes terrible poetry for the woman who rejected him.

Don Juan is Jack Tanner's philosophical ancestor and the legendary 16th-century Spanish figure, appearing in an extended dream sequence. Having tired of his earthly reputation as a hedonistic lover, he now seeks pure intellectual contemplation and desires to leave Hell for Heaven to escape endless talk of romance.

Dona Ana is an older woman who strictly upheld religious morality in life but wakes up entirely surprised to find herself in Hell. Highly concerned with social appearances and what others think, she engages in deep philosophical arguments regarding gender roles and human duty.

The Statue is the spirit of Dona Ana's father, who prefers to manifest as his marble monument because of the immense admiration it received on earth. He actively avoids intellectual philosophy, preferring to focus entirely on his own enjoyment by leaving the boredom of Heaven for the comforts of Hell.

The Devil is the ruler of Hell, presenting himself as a charming host who offers eternal pleasure without any moral responsibility. He is deeply romantic and constantly annoyed by cold, intellectual philosophizing, preferring emotional sentiment and indulgence.

Miss Ramsden is Roebuck Ramsden's unmarried sister. She is rigidly conservative and unforgiving, acting as the ultimate enforcer of social propriety within their social circle.

Rhoda is Ann's younger sister. She is heavily managed by her family members, who use her safety and propriety as an excuse to orchestrate their own social maneuvers.

Louisa is Henry Straker's sister, a working-class woman whose strict adherence to her own social code causes deep heartbreak for a former suitor.