All The Facts You Never Needed To Know About Ernest Hemingway's Sex Life

As a member of the Lost Generation, Ernest Hemingway participated in the post-WWI intellectual circle that influenced 1920s culture in Europe and the United States. Throughout his life, Hemingway's works incorporated contradictory themes of adventure, strength, and vulnerability.

Hemingway's private life was just as complex as his writing. His friendships with fellow authors like F. Scott Fitzgerald may have blurred the lines of traditional masculinity, something he seemingly tried to make up for by acting like a jerk. Despite the many times Hemingway was married, the ambiguity of his sexuality reveals how extremely conflicted the writer may have been in discovering his identity.

  • Hemingway Was Unable To Perform After His First Wife Left Him

    Ernest Hemingway's first wife, Elizabeth Hadley, knew that her husband was carrying out a secret relationship with Pauline Pfeiffer. She gave him an ultimatum: he had to spend 100 days without his mistress for Hadley to give him another chance. If he still loved Pauline after the time period, she would grant him a divorce. Hadley grew impatient and decided to leave Ernest after about 75 days. By that point, Hemingway was considering ending his life, which he blamed on being away from Pauline.

    Hadley divorced Hemingway, and he reconnected with Pauline. After their reunion, however, he was unable to get an erection. He tried everything - "all kinds of inducements, such as Spanish fly, Chinese potions, a variety of pills, electrodes fastened to [his] testicles," but nothing worked. Pauline suggested he pray, and Hemingway balked at the idea.

    Hemingway remarked: "I'd feel kind of foolish getting down on my knees and asking Jesus to give me an erection." He gave in, however, and prayed at a Catholic church. That same night, he was able to have relations with Pauline in a way that was as "good a session as [they'd] ever had."

  • Observers Saw Sexual Tension Between Hemingway And F. Scott Fitzgerald

    Hemingway told a story about an encounter at Michaud's, a restaurant in Paris. In the men's room Hemingway looked at F. Scott Fitzgerald's shaft after Fitzgerald expressed insecurities. Hemingway assured his friend

    You're perfectly fine [...] You are O.K. There's nothing wrong with you. You look at yourself from above and you look foreshortened. Go over to the Louvre and look at the people in the statues and then go home and look at yourself in the mirror in profile.

    Fitzgerald replied, "Those statues may not be accurate," to which Hemingway responded, "They are pretty good. Most people would settle for them."

    The exchange between the two men may have been exaggerated by Hemingway - a not-so-subtle attempt to secure his masculinity over Fitzgerald - but it also indicates that there may have been some sexual tension between the two men. Even with Hemingway's frequent shows of masculinity, not everyone was convinced of his manliness. Fitzgerald's wife, Zelda, characterized Hemingway as "a pansy with hair on his chest," and she had suspicions that her husband was in a homosexual relationship with him.

  • Hemingway's Mother Used To Dress Him Like A Girl, Which He Resented

    Hemingway's mother, Grace, was a trained singer who aspired to a career in theater. During the hours she spent practicing, her husband, Clarence, who went by Ed, took over household duties. He cooked, cleaned, and filled the role of homemaker. Ed was an obstetrician. He enjoyed baking and was famous for his doughnuts.

    Ed Hemingway was an avid outdoorsman, a hobby his son adopted with gusto. Grace would sometimes fire rounds while holding her son in her arms. She also dressed young Ernest up as a girl at times and introduced him as a twin sister to his older sibling, Marcelline, and the boy reportedly grew to hate his mother.

    According to his letters, Hemingway took satisfaction when, later in life, he was the dominant force in his family. He didn't attend her memorial service when she passed in 1951.

  • Hemingway's Second Wife Pursued Him With A Vengeance

    Hemingway met Pauline Pfeiffer in 1925 as he made his way around the Parisian intellectual scene. The Pfeiffers were from a wealthy family, and Pauline started spending more and more time with Hemingway, his wife Elizabeth Hadley, and their young son, Jack. Pauline then romantically pursued Hemingway:

    [She] never lost [the] pretense that she was Hadley's best friend at the same time - she was sending letters to them both [...] And the letters to Ernest were, as one might imagine, letters to a lover. And the letters to Hadley were sort of eerily asking for approval.

    Pauline inserted herself into the Hemingway family, offering gifts to Hadley and Jack. She invited the couple out for expensive dinners, but Hadley often stayed home with Jack. One night after a meal, Pauline invited Hemingway back to her apartment, and they began a not-so-secret sexual relationship.

    Hemingway claimed to be in love with both Hadley and Pauline at the same time. Fitzgerald cautioned Hemingway that Pauline was on a mission to find a husband and would do anything to have him to herself. Hadley found out about the affair while the group vacationed on the French Riviera. She gave her husband an ultimatum, although she divorced him before he could fulfill or fail to meet her demands. After his marriage was over, Hemingway married Pauline in 1927.

  • His First Love Burned Him, Leaving Him Broken-Hearted And Jaded

    During WWI, Ernest Hemingway, working as an ambulance driver in Northern Italy, was hit with shrapnel and spent time in the hospital while recovering. While recuperating in 1918, Hemingway met Agnes Von Kurowsky, an American nurse with whom he fell madly in love. The two began a romance when Hemingway was only 19, and Agnes was 26.

    Over the following months, they wrote to each other often but spent little time together. Agnes hinted that they would be married in a few years, but was concerned about her nursing career and their age difference. In 1919, Agnes sent him a letter ending their relationship. She wrote "[I'm] still very fond of you, but it is more as a mother than as a sweetheart."

    Hemingway was devastated, but they continued to correspond, and he eventually wrote about their relationship. Agnes was the inspiration for Catherine Barkley, the heroine in A Farewell To Arms. The male character, Henry, was a semi-autobiographical figure who left his fellow soldiers to be with Catherine, only to watch her pass while giving birth to their stillborn child.

  • Some People Who Met Hemingway Described Him As 'Androgynous'

    When Lady Emerald Cunard, an American socialite, met Hemingway in Paris, the two intellectually sparred, discussing politics, literature, and even the value of beards on men. After their conversation was over, however, Lady Cunard confessed to her friend and literary critic Cyril Connolly:

    I was startled [...] Not a bit what I expected. You may think it bizarre of me but he struck me as androgynous [...] It is not the mot juste, perhaps. But that's how he struck me. Distinctly emasculated.

    Associating Hemingway's work with androgyny has become part of the large body of scholarship on the topic. According to some scholars, Hemingway created androgynous characters and relationships without clear gender codes.