Aileen Pringle and Valentino, of which Mencken wrote an account, some weeks after Valentino had died. Mencken does not name her but describes her as "discreet as she is charming." Ralph Barton, American artist, was also a devoted friend and used her as the model for "Dorothy" in his illustrations for "Gentlemen Prefer Blondes" by Anita Loos. Another admirer was George Gershwin who met her in Hollywood and wrote much of the Second Rhapsody at her Santa Monica, California, home. Her wit, keen intellect and sparkling personality made her a sought-after companion. After her 1926 divorce from Charles Pringle, Aileen Pringle further
Anita Loos a devoted admirer of H. L. Mencken and when he was in New York, she would take a break from her "Tuesday Widows" and join his circle, which included Theodore Dreiser, Sherwood Anderson, Sinclair Lewis, Joseph Hergesheimer, essayist Ernest Boyd and theater critic George Jean Nathan. Loos adored Mencken with what may have been love and preferred this group over the Round Table. She gradually realized Emerson paled in comparison to someone like Mencken, and disappointingly, high-IQ gentlemen didn't fall for women with brains, but those with more "downstairs". In 1925, on the train to Hollywood for another Talmadge picture,