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.

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.

En naiv jente på jakt etter kjendisstatus i 1950-tallets Hollywood opplever at en romanse med en kjekk sjåfør kompliseres av den eksentriske sjefen hennes, Howard Hughes.