In September 1921, Rhinelander began a romance with Alice Beatrice Jones (July 19, 1899/1900 – September 13, 1989),the daughter of a working class family. The two met while Rhinelander was attending the Orchard School in Stamford, Connecticut, an inpatient clinic where he was seeking treatment to help him overcome extreme shyness and to cure his stuttering.Jones was a few years older than Rhinelander and the daughter of English immigrants; her mother was white and her father was of mixed race (then termed “mulatto”). It was reported that, during their three-year relationship, Jones’ father, George, attempted to dissuade the couple from continuing their romance. George Jones reportedly tried appealing to Rhinelander that his family would never accept his daughter due to their differences in class.However, Alice Jones would eventually file court papers, denying that her father ever made this move. In February 1922, Rhinelander’s father, Philip, attempted to end the relationship by sending his son away on to Bermuda on a chaperoned excursion that would separate the couple for two years, as he traveled to Washington D.C., Havana, Panama and California. In October 1922, Philip Rhinelander placed his son in an Arizona private school. However, the couple kept in contact through letters, as evidenced by letters produced at the trial, and when Leonard Rhinelander turned 21 years old, he returned to New York. On October 14, 1924, he married Jones in a civil ceremony at New Rochelle’s city hall. The marriage certificate listed both the groom and the bride as “white.” Once Jones’ ethnicity came into question, the fact that her marriage license identified her as “white” was reported, implying that she had sought to hide her mixed racial ancestry. During the trial, Jones’ attorney asked Leonard Rhinelander whether the city hall clerk who had filled out their marriage license had asked either of them whether they were white or “colored.” Rhinelander said the clerk had not.

The newlyweds rented an apartment in New Rochelle, ordered furniture and moved in with Jones’ parents in Pelham Manor while setting up their household. Rhinelander did not tell his family of the marriage, but continued to stay in Manhattan and work at Rhinelander Real Estate Company during the week.

Although the couple attempted to keep their marriage secret (Jones’ sister Grace claimed the couple even paid reporters not to announce their marriage), the press soon announced the news of the marriage. Because of the Rhinelanders’ fortune and social standing, New Rochelle reporters were eager to learn about Jones’ background and began investigating. Reporters discovered that Jones was the daughter of English immigrants and her father, George, was a “colored man.” The Rhinelanders got wind that reporters had discovered Jones’ heritage and attempted to keep the information out of the papers. According to one article printed in the New York Daily Mirror, the Rhinelanders sent an “agent” to warn the editor of the New Rochelle Standard Star that if the story was printed, there would be “dire punishment.” The editor ignored the threat and on November 13, 1924, the New Rochelle Standard Star printed the story with the headline, “Rhinelander’s Son Marries Daughter of Colored Man.”

The New York Evening Post picked up the story but was hesitant to identify Jones’ father as black. They instead referred to George Jones as being “West Indian”. Other papers picked up the story but most were also careful to omit the racial angle, choosing instead of focus on the differences in Rhinelander and Jones’ social class (in varying papers, Jones was identified as a nanny, nurse or laundress). Other media accounts referred to the jobs of Jones’ family, her father was variously identified as a cab driver or stagecoach driver and her uncle a butler, which at the time were understood to be positions held mainly by black people.The Hearst-owned tabloid New York Daily Mirror however ran a front-page banner headline: “RHINELANDER WEDS NEGRESS/Society dumbfounded.” Most larger city papers were wary of printing such a scandalous story due to the Rhinelanders’ wealth and prominent social status.