The daughters of a wealthy Chicago medical doctor, Helen Dudley and her artistically inclined sisters—known as the “Dudley girls”—were famous in Chicago’s literary circles for their wit, exuberance, and talent. Dudley and her sister Dorothy (Dudley) Harvey wrote poetry and published poems in the first edition of Poetry; Helen’s poems were included in Harriet Monroe’s New Poetry: An Anthology (1917). 

In the early teens, Helen Dudley studied Greek at Oxford University. She and the philosopher Bertrand Russell began an affair in 1914; Dudley moved to England to be with Russell, but the affair ended during World War I, a shock from which she apparently never recovered. Her portrait, painted by Vanessa Bell around 1915, is at the Tate Gallery.