Through the influence of her cousin Sara Collins, Riley moved to Chicago in 1885 to teach primary grade girls at the Park Institute finishing school. In her spare time she learned French and music at the school. At the end of her term at the school she moved to Nebraska to work with her brother-in-law Harry Palmer, copying records from the county clerk's office, which led to work at the Statehouse in
Lincoln, Nebraska. When she returned to Chicago, Riley resumed weekly French lessons while rooming on Warren Ave in Chicago. It is here she met her neighbor Dorothy (Jessie) L. Gaynor in 1896. Gaynor started a music class, which Riley joined, and they soon exchanged lessons; Riley taught Gaynor French, while Gaynor taught Riley music composition. Riley made up some lyrics to finish her lesson on lullabies, and Gaynor was so impressed she asked her to write lyrics for a song for her daughter. They quickly began collaborating with Riley's writing lyrics and Gaynor's putting them to music. The songs they collaborated on were mostly for children, finding inspiration from the domestic scene. Their best-known collaboration is called "Slumber Boat", which Gaynor sang in her recital work. Soon, the song received notoriety and they were approached by an agent from John Church Company of Cincinnati, Ohio, who wanted to publish a children's kindergarten book. The resulting book,
Playtime Songs, was very successful all over the United States and in Canada, England, and English schools in Japan. In 1901, Riley got in the habit of having her friend Marie Bartlett over for tea on Thursday afternoons. Initially, she would read while Marie sewed and they discussed current events. Soon other neighbors joined in, and before long, the expanding group was named the Riley Circle. The Riley Circle met at her home in Evanston for many years following the same format, ==References==