Gambler Nathan Detroit has few options for the location of his big craps game. Needing $1,000 to pay a garage owner to host the game, Nathan bets Sky Masterson that Sky cannot get virtuous Sarah Brown out on a date. Despite some resistance, Sky negotiates a date with her in exchange for bringing people into her mission. Meanwhile, Nathan's longtime fiancée, Adelaide, wants him to go legit and marry her.

It's Hollywood, 1958. Small town beauty queen and devout Baptist virgin Marla Mabrey, under contract to the infamous Howard Hughes, arrives in Los Angeles. At the airport, she meets her driver Frank Forbes, who is engaged to be married to his seventh grade sweetheart and is a deeply religious Methodist. Their instant attraction not only puts their religious convictions to the test, but also defies Hughes' number one rule: No employee is allowed to have any relationship whatsoever with a contract actress. Hughes' behavior intersects with Marla and Frank in very separate and unexpected ways, and as they are drawn deeper into his bizarre world, their values are challenged and their lives are changed.

Wealthy socialite Charlotte Cartwright and her dear friend Alice Pratt, a working class woman of high ideals, have enjoyed a lasting friendship throughout several decades. Recently, their lives have become mired in turmoil as their adult children’s extramarital affairs, unethical business practices, and a dark secret threaten to derail family fortunes and unravel the lives of all involved. Charlotte and Alice decide to take a breather from it all by making a cross-country road trip in which they rediscover themselves and possibly find a way to save their families from ruin.