According to Frank Capra's autobiographical book, he dismissed using Barbara Stanwyck when their interview went badly. Frank Fay, Stanwyck's husband at the time, called Capra up, furious over Stanwyck's having come home from the interview, crying. Capra blamed Stanwyck, saying she acted like she didn't even want the part. Fay responded, "Frank, she's young, and shy, and she's been kicked around out here. Let me show you a test she made at Warner's." (The test was for "The Noose," a Broadway play Stanwyck starred in and also a film made without Stanwyck in 1928 by John Francis Dillon for First National.) Capra was so impressed that he left the screening immediately to get Harry Cohn, who ran Columbia, to sign up Stanwyck as quickly as possible.
Frank Capra wrote the first draft of Ladies of Leisure, before Jo Swerling took over. According to his interview "I went to my hotel, locked myself in my room and for five days pounded out a rewrite story of the plot I'd heard, interrupting the writing only long enough for black coffee, sandwiches and brief snitches of sleep. I was simply writing a newspaper yarn with a longer deadline than usual. The result was Ladies of Leisure."
Capra later wrote that he was so smitten with the young Barbara Stanwyck at the time, he would have asked her to marry him if they both had been free at the time.
Because the studio was so impressed with her work on this film, Columbia signed Barbara Stanwyck to a four picture contract.
When aboard the ship to Havana, Bill tells Kay he will see her "twelve miles out". He is referring to the territorial limit of U.S. laws - when the ship's bar could open and legally serve alcohol, as this was still during Prohibition.