John Singer Sargent always admired Amelie Gautreau and hoped to paint her to elevate his status as a portraitist. He first painted her lover, Dr. Pozzi, in order to work his way into her sphere. And then painted Madame Gautreau Drinking a Toast as a gift to Amelie's mother. This painting began the slow progression of admiration into obsession. Sargent continued to paint Amelie repeatedly on account of his infatuation and dedication to perfecting the complicated portrayal of Amelie Gautreau. 

In Madame Gautreau Drinking a Toast, his first painting of Amelie, he overly romanticized every brushstroke. The candlelit setting highlighted her soft, lovely, and alluring features. In this painting Sargent fails to reflect Amelie's artificial skin tone shown in Madame X. Amelie glows against the dark and blurred background, highlighting her outstretched arm and neck. Amelie tilts her head to the left to draw attention to her beautiful profile and long nose. Her gaze focuses at her glass, un-enthusiastically participating in a toast. 

The book Strapless by Deborah Davis suggests Sargent’s was interested in men rather than women. A small ink sketch by Sargent exists that people thought of for years as preliminary sketch for Sargent’s Madame Gautreau Drinking a Toast, due to the perfect alignment and identical orientation of the heads. Recent inspection theorizes that the head actually belongs to Albert de Belleroche, Sargent's "best friend" and more likely lover. Sargent masks his sexual preference by painting a woman, but the painting, like the painter, may be holding something back.