Darling met Butch Cassidy in Vernal, Utah in early 1896. Ruby Ann was one of the few females known to have traveled and robbed with the Wild Bunch after leaving Vernal. They remained together until Cassidy's apparent death (or disappearance) shortly after the beginning of the 20th century.
Following Cassidy's disappearance, Ruby Ann married Bob Meeks and had a daughter. Bob Meeks died when Ruby Ann was pregnant with her second child. Ruby Darling Meeks worked as a prostitute and continued her criminal career. She was involved in two separate incidents in which she was arrested for robbery and assault, the latter including shooting and wounding a man in 1907.
In September 1921, Ruby Ann was arrested along with two men for holding up the First National Bank in Vernal. Ruby Ann was sentenced to five years in the Utah State Prison, where she died of a perforated ulcer on January 21, 1926 at age 38.