Hannah Gluckenstein was born to a wealthy Jewish family on August 13, 1895. Her father, Joseph Gluckenstein, owned the J. Lyons & Co. Coffee House and catering empire in London and her mother, Francesca Hall, was an American opera singer. The parents were not supportive of their daughter's artistic pursuits, but Hannah received her only systematic art training at their expense at St. John Wood School of Art in London from 1913 to 1916.

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The dynamic young woman then traveled to Lamorna, Cornwall where she worked with other artists of the "Newlyn School," a group of landscape painters who formed an artists' colony at Newlyn, Cornwall. On her twenty-first birthday, Gluck's father gave her a trust fund that allowed her to pursue an independent life. By that time, Hannah had cropped her hair, shortened her name to "Gluck," and dressed exclusively in male attire.

Using a portion of her trust funds, Gluck bought a studio in Cornwall. It was there in 1923 that she met the American expatriate artist Romaine Brooks. The two women painted each other's portrait in Gluck's studio.

Brooks' famous portrait of Gluck, Peter (a Young English Girl), was executed between 1923 and 1924. During 1925, Gluck painted a daring self-portrait in which she depicted herself wearing a shirt, tie, suspenders, and beret, while smoking a cigarette. The same year Brooks' portrait of Gluck dressed in male attire was shown in solo exhibitions in Paris, London, and New York.

At the end of the 1920s, Gluck's father increased her capital, allowing her to purchase a larger home, named Bolton House, in Hampstead. Shortly after she was established in Bolton House, she met the decorator and society florist, Constance Spry.

Spry's talents as a decorator and florist were in high demand among the aristocracy and the wealthy. She and Gluck were together from 1932 to 1936. During this time, Gluck painted several floral paintings inspired by Spry's arrangements.

Spry decorated the Fine Arts Society galleries for Gluck's third exhibition in 1932. The walls were paneled in white, modern furniture was added, and each room featured one of Spry's floral arrangements. All of the paintings were hung in the "Gluck frame" that the artist designed and patented. The frame was a triple-tiered design that made her paintings an integral part of the gallery's architecture.

The relationship between the two women not only influenced the subject of Gluck's work, but the contacts made through Spry's society connections also furthered the artist's career. Many of Spry's clients commissioned and bought Gluck's floral paintings.

Spry also influenced Gluck's attire, turning her look into haute couture with fashion designs by Victor Stribel and Elsa Schiaparelli. While the two women enjoyed each other's company, many of Spry's clients found Gluck to be fussy and irritating.

In 1936, Spry broke off her relationship with Gluck, but by then the artist had already met and begun to fall in love with Nesta Obermer (Ella Ernestine Sawyer), a socialite who was involved in a marriage of convenience to the American businessman Seymour Obermer. The two women enjoyed concerts, poetry readings, and the theater together.

Although Nesta later systematically destroyed all evidence of her relationship with Gluck, a visual record of Gluck's feelings for Nesta exists in the double portrait she painted entitled Medallion.

This work was painted in celebration of what Gluck called her marriage to Nesta on May 25, 1936. The visual statement of two lovers merging into one being expressed an ideal that proved impossible for the women to sustain. The couple was together until 1944, when Nesta decided that she had to break off their relationship because Gluck had become too demanding and possessive.

Soon after England declared war against Germany in 1939, the Auxiliary Fire Service commandeered Bolton House. The War Artists Commission turned down Gluck's application for enlistment. Given the losses she had experienced and the rejection she felt, Gluck understandably began to sink into a deep depression.

Her suffering is already evident in a self-portrait she painted in 1942, two years before she and Nesta parted company. The artist depicted herself with her head tilted back, looking grimly down on the viewer with a defiant and combative expression.