It’s the early 1930s, and amidst a small funeral gathering at the gravesite of Essie May Loggins, two female acquaintances stand by, while her 9-year-old daughter, Addie, mourns. Arriving fashionably late is Moses Pray, a charming young man with a questionable past, revealing that he was one of Essie's lovers. The attendees speculate about a possible resemblance between Moses and Addie, hinting at his potential paternity, which Moses quickly denies. However, the women soon persuade Moses to drive Addie to her relatives in St. Joseph, Missouri.
Frustrated yet seeing an opportunity, Moses, a seasoned con artist, blackmails a local man with knowledge of Essie's affairs. Under the ruse that the man might be Addie's father, he cajoles $200 from him, which he plans to use for his own gain, including purchasing a new car. But Addie, not one to be easily manipulated, overhears their exchange and demands the money, arguing it is her rightful share. Perceiving Addie’s cleverness as both a threat and an asset, Moses reluctantly agrees to repay her.
As they travel together, Addie learns about Moses' scams, particularly his guise as a Bible salesman. He charms widows by suggesting that their deceased husbands had ordered personalized Bibles. This trick works with a woman named Pearl, who, believing in her husband's sentiment, pays up, sealing their con. Yet, Addie proves her worth by cleverly saving Moses from being caught when a lawman stops by, and she manages to charm the officer into their favor, raising the Bible's price in the process.
As they continue their escapades, they encounter an unexpected hurdle when Moses becomes romantically entangled with Trixie Delight, a showgirl from a traveling carnival. Jealous and feeling sidelined, Addie initially resents Trixie, but a candid conversation reveals Trixie's transient nature with men. Although reassured, Addie is heartbroken when she finds their savings squandered on a new car, prompting her to plot revenge against Trixie with the assistance of Trixie's maid, Imogene. They cleverly orchestrate a scandal that leads to Trixie's downfall, allowing Moze to once more partner with Addie.
Their criminal exploits become even bolder as they seize the chance to steal liquor from a local bootlegger. However, their luck takes a turn when they are caught by the sheriff after their crime. With their creativity, Addie devises a daring escape, leading to their flight from authorities across the border into Missouri.
As they settle into a new routine as partners in crime, the prospect of a massive score comes up for a wealthy gentleman. But as they pursue their ambitions, the past catches up with Moses when the Kansas sheriff seeks vengeance, brutally assaulting him. Witnessing the aftermath, Addie realizes the seriousness of their situation, prompting Moses to reconsider their partnership. He eventually takes her to her aunt's home, though she remains less than enthusiastic about her new living situation.
In a poignant twist of fate, as Moses wallows in regret after leaving Addie, she appears running towards him. Despite his feigned indifference and stern demeanor, he can’t hide the joy of seeing her again. Addie reminds him of the $200 he owes her, and in a flurry of unexpected events, they find themselves driving off together, embracing their unconventional yet undeniably strong bond.
