A large number of women played major roles in Dreiser's life from his early years as a Chicago and St. Louis newspaperman until his death. He appears to have coined the word “varietist” to describe a man's desire for a number of simultaneous sexual relationships, all of them intense but none permanent. In Dreiser's case, these relationships also often involved an age difference of several decades between himself and the woman of the moment. Mencken, as he gradually learned about Dreiser's private life a few years after their initial meeting in 1908, commented that “women occupied an enormous place in his life—a place, indeed, that seemed to me, and to many others, to be inordinate. I sometimes wondered how, with four or five intrigues going on at once, he found time for his really heavy stint of daily writing.”

There is thus the temptation to view Dreiser, as he is indeed portrayed in W. A. Swanberg's influential 1965 biography, as a casual seducer of younger and younger women who also exploited their infatuation with him by using them as typists, researchers, and editors. There is indeed much to support this view in Dreiser's diary of his New York years of 1917–19, when a day's record of his activities often consists of alternating trysts with several women and bouts of writing.

But the story of Dreier's relationship with women is more complicated than that of the adventures of a modern Don Juan. Dreiser in June 1917 was having simultaneous affairs with Lillian Rosenthal, Louise Campbell, and Estelle Kubitz, with Kubitz deeply troubled by his lack of faithfulness. Dreiser commented in his diary for June 7, “I must be very calloused. [Kubitz's] love moods torture me at the moment, yet a little while later I forget them. And I believe that it would almost kill me—be absolutely impossible for me to be faithful to one woman. At this date it would be almost the severest strain I have yet endured.”