Elaine Orr was a captivating figure in the New York City literary and artistic circles of the early 20th century. As John Dos Passos recalled in his memoir, "The Best Times," she was a muse and a social hub, particularly for the Harvard Monthly crowd, which included e.e.cummings. Dos Passos described her as "the poet's dream," a "Blessed Damozel" whose beauty and charm drew admiration and affection.

Elaine's early life, however, was marked by turbulence. Despite attending finishing schools befitting a wealthy industrialist's daughter, she experienced the early loss of her parents and was raised by an uncle. In 1916, she married Scofield Thayer, who later transformed "The Dial" into a prominent arts magazine. Their marriage was unconventional; Thayer maintained a separate residence and relied on Cummings to entertain Elaine.

Cummings' friendship with Elaine evolved into a love affair, seemingly with Thayer's approval. In 1919, Elaine gave birth to Nancy, with Cummings recognized as the father, though Thayer assumed paternity. Cummings, however, struggled to provide emotional and paternal support, focusing on his artistic pursuits. Elaine eventually divorced Thayer and, in 1923, urged Cummings to marry her.

Their marriage in 1924 was short-lived. Elaine's desire for financial security and a conventional life clashed with Cummings' bohemian lifestyle. Within months, she left him for Frank MacDermot, a wealthy banker, and sought a divorce. Cummings was devastated, and the MacDermots denied him access to Nancy.

Elaine's motivations were complex. She expressed a desire for a "constructive" and "happy" life, contrasting Cummings' perceived inability to adapt. She acknowledged her own "neurotic" tendencies but emphasized her strength and self-awareness.

Cummings' poems reflected the evolving nature of their relationship. Early works idealized Elaine, portraying her as a "Lady" deserving of chivalric praise. As their relationship deepened, his poems became more sensual and celebratory of their intimacy. However, their eventual separation led to bitter and satirical depictions of Elaine as a betrayer and a fickle "butterfly."

John Dos Passos, in his novel "Manhattan Transfer," drew inspiration from Elaine Orr for the character of Elaine Thatcher. Thatcher, like Orr, is beautiful and ambitious, seeking a materially comfortable life. However, Thatcher is more assertive and self-reliant, pursuing an acting career and navigating complex relationships.

Dos Passos portrays Thatcher as a femme fatale, moving from man to man and leaving emotional wreckage in her wake. She is depicted as cold and calculating, yet also conveys a sense of underlying anguish and unfulfilled longing. Her eventual marriage to George Baldwin, a wealthy lawyer, is portrayed as a pragmatic choice rather than a romantic one.

Dos Passos' portrayal of Elaine Thatcher is more nuanced than Cummings' poetic depictions of Elaine Orr. His distance from the situation allowed him to create a more complex character, exploring her motivations and contradictions. Cummings' poems, on the other hand, served as emotional reflections of his personal experiences with Elaine, capturing the highs and lows of their tumultuous relationship. Both writers, however, presented Elaine as a captivating and enigmatic figure, embodying both allure and vulnerability.