Maid to Order

A bratty, self-indulgent heiress whose carefree lifestyle masks a lack of discipline. After losing her privileges, she learns to value hard work, loyalty, and genuine friendships as she rebuilds her life as a live-in maid.

A fairy godmother figure who enacts the moral change in the Montgomery family. She explains the consequences of Charles’s wish and guides Jessie toward independence, even when Jessie resists at first.

Chauffeur and aspiring songwriter who becomes Jessie’s love interest and anchor as she learns to balance affection with responsibility. He supports her growth and shares a creative dream of breaking into the music world.

A flamboyant Malibu lottery winner who, with his wife Georgette, embodies the overstated wealth Jessie's world is leaving behind. His home, tastes, and expectations highlight the class contrasts at the story’s center.

The Starkeys’ ambitious matriarch who aims to translate newfound wealth into a music career. Her dynamic with the household staff reveals the pressures and ambitions that accompany sudden fortune.

The Starkeys’ daughter, a young member of a family freshly immersed in money who represents the glittering but scrutinized side of the social world Jessie steps into.

The Starkey household cook and a failed singer who befriends Jessie. She embodies resilience and the value of pursuing one’s dreams while staying practical.

A fellow live-in maid who forms part of the supportive staff network. She helps Jessie navigate the realities of service work and the camaraderie that comes with it.

Jessie’s widowed philanthropist father, whose wish sets the events in motion. His indulgence and guilt drive the family’s arc toward learning responsibility and connection.