After an arm injury ended her aspirations as a pianist, Jenkins gave piano lessons in Philadelphia to support herself; but around 1900 she moved with her mother to New York City. In 1909, in her early forties, Jenkins met a 33-year-old British actor named St. Clair Bayfield; they began a vaguely defined cohabitation relationship that continued the rest of her life. Upon her father's death later that year, Jenkins became the beneficiary of a sizable trust, and resolved to resume her musical career as a singer, with Bayfield as her manager. She began taking voice lessons and immersed herself in wealthy New York City society, joining dozens of social clubs. As the "chairman of music" for many of these organizations, she began producing lavish "tableaux vivants"—popular diversions in upper-crust social circles of that era. In each of these productions, Jenkins would invariably cast herself as the main character in the final "tableau", wearing an elaborate costume of her own design. In a widely republished photograph, Jenkins poses in a costume, complete with angelic wings, from her "tableau" inspired by Howard Chandler Christy's painting "Stephen Foster and the Angel of Inspiration".