Grover Cleveland was the second man who entered the presidency as a bachelor, but the only one who began his term as a single man and ended it as a married man (Buchanan, the only other bachelor elected to the presidency remained unmarried throughout his Administration). For the first fourteen months of the Administration, his youngest sibling sister Rose Elizabeth Cleveland served as the official hostess. Although she was developing her own independent career as a writer, editor and lecturer, she had begun to assume management of his domestic life as Governor of New York towards the end of his term. She presided over the party of friends and family who gathered in the governor’s mansion in Albany, New York to celebrate his victory in the 1885 presidential election.

Rose Elizabeth Cleveland, always called "Libbie" by her friends and family, was born 13 June, 1846; she was educated at the Houghton Seminary and taught literature in Lafayette, Indiana and later at Hamilton College.

Publicly, Rose Cleveland was considered a "bluestocking," a serious, academic woman with little patience or interest in those subjects which women of her era were socialized to find most compelling, such as clothing, decorating and entertaining. This is only a partial truth; as she revealed in one of her books, Rose Cleveland believed strongly in adhering to the societal conventions which dictated behavior and gender interaction. Her private letters, however, do reveal the frustration she experienced as a result of her nevertheless feeling she must adhere to the unwritten code dictating the protocols followed by Victorian-era First Ladies which limited her from dining in private homes or appearing in the public markets. That code did, however, permit First Ladies to appear in public theaters and like Mary Lincoln and Julia Grant, Rose Cleveland greatly indulged this personal passion. She had a particular love for the contemporary musical theater productions of Gilbert & Sullivan and managed to even coax her hard-working brother out of the White House to attend the theater with her.

Rose Cleveland’s facility with the classics prove useful to her during the long hours she was required to stand while shaking hands with endless lines of guests at White House receptions. Finding this especially dull, she later revealed that she was conjugating Greek and Latin verbs in her mind during this process. While she largely remained disinterested in politics, she didn't hesitate to express her anti-Catholicism to the President in her warnings to him not to appoint too many "papists" to federal positions.

Most of her friends were theatrical or literary professionals. Rose Cleveland was herself notable as the first First Lady, though not a presidential wife, to publish books she wrote during her incumbency. Her first bookGeorge Eliot's Poetry and Other Studieswas published while she was in the White House, in June of 1885; it went through 12 editions in a year and earned her some $25,000. While still serving as First Lady, the following year she publishedYou and I: Moral, Intellectual and Social Culture, a 545 page treatise considering the changes wrought on 1886 American life. Her last book,The Soliloquies of St. Augustine, translated into English,With Notes and Introduction by the Translatorwas published in 1910 by Little, Brown, and Company.

Rose Cleveland’s last efforts as First Lady were to enact the arrangements dictated by her brother for his White House wedding to Frances Folsom.

Following the assumption of the First Lady role by the new Mrs. Cleveland, Rose Cleveland moved to Chicago, where she worked as an editor of the city’sLiterary Lifemagazine for three years. The income she received from her book royalties soon accumulated and proved considerable. Able to support herself well by lecturing and writing, Rose Cleveland left her job in Chicago. She then returned to the city of Utica, New York, where she purchased her own home. Beginning in 1889, however, she had also begun heading south to Naples, Florida. There she bought two property lots for twenty dollars and had her own cottage built there on Gulf Street, five blocks from the pier.

While there, the 44 year old Rose Cleveland began a romantic friendship with Evangeline Simpson, a wealthy 30-year-old widow. It soon developed into a physical love relationship. In one of her first letters to the woman she called “Eve,” the former First Lady declared, "Ah, how I love you…you are mine by every sign in Earth and Heaven--by every sign in soul and spirit and body…Oh, Eve, I tremble at the thought of you. Sweet, Sweet, I dare not think of your arms." Later in 1890, Rose Cleveland proposed that they meet in New York but rather than stay with the former President and First Lady at their Madison Avenue home, she wanted to share the same hotel room with Eve Simpson, an arrangement the latter agreed to.

After returning to their respective homes, the two women exchanged what can only be described as a series of increasingly erotic letters. "I tremble at the thought of you," Cleveland wrote. "I dare not think of your arms." Simpson, in return, addressed Cleveland as "my Clevy, my Viking, my Everything." The passion of Rose Cleveland’s letters to Eve Simpson only increased during their separations, declaring that the latter’s "long rapturous embraces” and “warm enfolding arms appease my hunger and quiet my breast--and carry us both in one to the summit of joy, the end of search, the goal of love!" When Simpson enclosed a photo of herself in a letter, Cleveland replied that "the look of it [is] all making me wild."

The two women decided to live together, an arrangement which continued until Eve Simpson chose to follow a more conventional path. In 1895, she became engaged to Henry Benjamin Whipple, the widower Episcopal bishop of Minnesota. She was 36 years old and he was 74 years old. The decision, Rose Cleveland wrote, hurt her deeply. Nevertheless, in a letter she wrote to Bishop Whipple on Executive Mansion stationery while visiting her brother during his second term, she expressed her genuine wishes that the couple had found love with each other.

He died in 1901, and after Evangeline had observed the traditional one-year of mourning, she abruptly left for Europe and was joined by Rose, the two women living together in Italy. The two women settled there permanently in 1910. Evangeline Whipple lived for 12 years beyond Rose Cleveland, who died on 26 November, 1918. The two women are buried alongside each other in Italy.

Bishop Whipple died in 1901 and within four years Rose Cleveland and Eve Simpson Whipple had resumed their contact by letter. They decided to both leave the United States and live together in Italy. When they sailed on a Cunard Line ship to Europe in 1910, the two women unapologetically booked a cabin together.

They settled in Bagni di Lucca, in Tuscany, living a life unbothered by publicity, until Rose Cleveland died of the Spanish flu epidemic on 22 November 1918 epidemic.

Despite her status as a former First Lady, her remains were not returned to the United States, but rather she was buried in the American Anglican Church Cemetery in the town where she had lived with Eve Simpson Whipple and another woman friend who had come to share their household. Upon her death in 1930, Eve Simpson Whipple was buried next to Rose Cleveland as stipulated in her will.