Born in Richmond, Virginia, she came to New York City in her early teens to study art. Her mother was Annie Ericsson Cudlipp, an Assistant Editor on the The Delineator in 1909 when Theodore Dreiser was Managing Editor. Dreiser became infatuated with Thelma, but her mother was strongly opposed to Dreiser's involvement with her daughter, which was platonic – Dreiser was married and twenty years her senior. Thelma's mother succeeded in breaking up the relationship by packing Thelma off to England and by reporting it to the directors of the Butterick Publishing Company, which cost Dreiser his job.
In England Cudlipp continued her training in art, winning but not accepting a Royal Academy scholarship. When she returned to America, she took lessons from Kenneth Hayes Miller, one of Dreiser's closest friends among painters. She became well known as an illustrator for various newspapers and magazines, such as Harper's, The Century Magazine, McClure's, and The Saturday Evening Post. In addition to her own work, she developed an interest in pre-Columbian sculpture, which she collected and promoted through lectures. She later developed a friendship with Dreiser, but it was not of a romantic nature. They exchanged letters with each other until Dreiser's death.
In 1918 she married Edwin Grosvenor, a successful attorney and cousin of former president Taft. Her husband died in 1930, and in 1933 she married Charles Seymour Whitman, who had been Governor of New York from 1915 to 1918. He died in 1947.
She died on April 2, 1983 in Greenwich, Connecticut. 
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