Libby Holman had a variety of relationships with both men and women during her lifetime, including Jeanne Eagels, Tallulah Bankhead, Josephine Baker, and, later in her life, writer Jane Bowles. Although friends observed her to be a "ball breaker" with men, she was tender and intimate in her same-sex relationships. Her most prominent relationship was with DuPont heiress Louisa d'Andelot Carpenter. The couple's relationship would last until Holman's death in 1971; during Libby's Broadway career in the early 20s, they would go out to parties and jaunts in Harlem dressed identically in men's suits in bowler hats, joined by other lesbian and bisexual contemporaries such as Tallulah Bankhead, Beatrice Lillie, Lucille Fay LeSueur, and Marilyn Miller. Carpenter was to play a significant part throughout Holman's lifetime. They raised their children and lived together and were openly accepted by their theater companions. She scandalized some by dating much younger men, such as American actor Montgomery Clift, whom she mentored.