Hemingway's parents reportedly had an unconventional arrangement, in which Grace, an ardent feminist, would agree to marry Ed only if he could assure her she would not be responsible for the housework or cooking. Ed acquiesced; in addition to his busy medical practice, he ran the household, managed the servants, and even cooked meals when the need arose.

Ernest Hemingway grew up with four sisters; his much-longed-for brother did not arrive until Ernest was 15 years old. Young Ernest enjoyed family vacations at a cottage in northern Michigan where he developed a love of the outdoors and learned hunting and fishing from his father. His mother, who insisted that all of her children learn to play an instrument, instilled in him an appreciation of the arts.

In high school, Hemingway co-edited the school newspaper and competed on the football and swim teams. Fond of impromptu boxing matches with his friends, Hemingway also played cello in the school orchestra. He graduated from Oak Park High School in 1917

In fall of that year, he moved to Chicago and became a writer for The Cooperative Commonwealth, a monthly magazine, while still working for the Star.

Hemingway, however, longed to write fiction. He began submitting short stories to magazines, but they were repeatedly rejected. Soon, however, Hemingway had reason for hope. Through mutual friends, Hemingway met novelist Sherwood Anderson, who was impressed by Hemingway's short stories and encouraged him to pursue a career in writing.

Hemingway also met the woman who would become his first wife: Hadley Richardson. A native of St. Louis, Richardson had come to Chicago to visit friends after the death of her mother. She managed to support herself with a small trust fund left to her by her mother. The pair married in September 1921.

Sherwood Anderson, just back from a trip to Europe, urged the newly married couple to move to Paris, where he believed a writer's talent could flourish. He furnished the Hemingways with letters of introduction to American expatriate poet Ezra Pound and modernist writer Gertrude Stein. They set sail from New York in December 1921.