New letters shed light on Hemingway’s unrequited love and early life.

On a recent afternoon in Boston, Betsy Fermano walked through an exhibition titled “Ernest Hemingway: Between Two Wars” at the John F. Kennedy Library and Museum. Among the artifacts—vintage photos, paintings, and handwritten stories from Hemingway—she spotted a family name in a manuscript on display: Coates.

Frances Elizabeth Coates was Fermano’s grandmother and Hemingway’s high-school classmate. He used a version of her name—“Liz Coates”—in his sexually charged 1923 story “Up in Michigan,” and her name resurfaces elsewhere in his work.

That’s because Hemingway was infatuated with her. The two briefly dated, though almost no one, until now, knew of their history. For Fermano, sixty-seven, a retired development executive, it wasn’t a surprise: she has ninety-nine-year-old letters from Hemingway that no one outside the family knows about.

“This is a really fascinating find,” says Sandra Spanier, a professor of English at Pennsylvania State University and general editor of the Hemingway Letters Project. “To find early letters like that—that’s extremely rare. It’s a fresh view of him. It would be of great interest to a future biographer.”

Spanier says the new letters bring Hemingway’s World War I experience “to light very vividly” and show a seldom-seen side of the budding author, since little material survives from that period.

“You hear him being flirtatious and kind of bragging, the way a teenage boy would. He’s trying to make her a little bit jealous,” she says. “But he’s also got this self-deprecating humor, which is quite charming. It’s a completely different voice from others we’ve heard in his letters.”

In 1918, not long after graduating high school, Hemingway headed to Italy to serve as a volunteer ambulance driver in World War I. After he was wounded by mortar fire, he spent some time in a Milan hospital, during which his mind returned to Coates.

The nineteen-year-old Hemingway remained so enamored of his former classmate that he wrote to his sister Marcelline, asking her to “call up Frances Coates and tell her that your brother is at death’s door. And that will she please, no excuses, write to him. Make her repeat the address after so that she will have no alibi. Tell her that I love her or any damn thing.”

Coates did write him back, although that letter is lost. What have survived are two previously unknown letters from Hemingway to Coates, kept in a trunk for decades. The correspondence dates to a time when Hemingway was not yet famous—he had only a handful of short stories to his name.

In one of the letters, dated October 15, 1918, Hemingway writes on American Red Cross stationery, on the back of hospital supper tray, “by the light of a candle stuck in a bayonet.” He goes on: “… I can now read, speak and write love letters in Italian … I never cared to bring myself to address anyone as ‘My treasure’ but a ‘Tesor a mea’ [sic] just runs out of the pen … Tis indeed a noble language and I’ll have to haunt the fruit stands in the States to find somebody to work it off on!”

If the implication was that Frances could be that somebody, she did not appear to bite. And yet other items in Fermano’s trunk show that she followed his life and career with interest. She held onto snapshots of a wounded Hemingway in Milan and some photos commemorating a canoe trip they took together. There’s also an envelope of newspaper clippings that track Hemingway’s rise to fame, chronicling his global adventures, his four marriages, and his suicide in 1961. Frances even kept Hemingway’s high school photo in her dressing room, where it occupied a small gold frame, surrounded by gold lace. And Fermano held onto an unpublished ten-page remembrance Frances wrote about growing up with “Ernie”: a unique document that offers intimate insight into the author’s teenage years in Oak Park, Illinois.

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Before I met Fermano, I’d chased down another mystery woman from Hemingway’s past, Annette DeVoe, via a little-seen poem featured in my book Hidden Hemingway. In the poem, the teenage Hemingway had pledged his love: “I’d gladly walk thru Hell with you / Or give my life.” I’d found DeVoe’s family, who confirmed that the pair had dated; in fact, DeVoe, like Coates, had kept a photo of Hemingway all her life. This ran contrary to previous biographies, which portrayed the budding author as preoccupied with outdoor pursuits and unlucky with girls.

Reviewing Hemingway’s letters from this period, I kept noticing Coates’s name alongside DeVoe’s. In fact, Hemingway’s sister had needled him with a mocking sonnet about his crush on Coates, perhaps in retaliation for his penchant for opening her correspondence to “find out what the dames think of me.”

“Frances his idol, with eyes of blue!” the poem begins:

He wonders if F Coates is looking his way

He straightens his tie, and heaves a great sigh

But oh how he jumps to see when sweet F.C. comes by!

No one likes Ernest, that is straight stuff

And when he writes his stories we all say Enough

The poem reflects the popular opinion of the teenage Hemingway: even his high school friends said they were more likely to see him with a fishing rod than a girl. In 1984, more than six decades after he’d graduated from high school, his former classmate and neighbor Marian Kraft Larson told the Chicago Tribune that although Hemingway wasn’t very “attractive to girls or with girls,” he was “very popular with the boys.”

Larson added: “Frances Coates was the only girl I remember seeing him with.”

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In our first phone call, I asked Fermano if she knew whether her grandmother dated Hemingway. Yes, Fermano said, she knew that Coates went out to dinner with the teenage Hemingway—but she suspected the interest was one-sided. In modern terms, Hemingway was stuck squarely in the friend zone.

“My grandmother always played it down, and they were always just friends,” Fermano remembers. “There may or may not have been a possibility of that relationship developing, but, at the time, Frances was being courted by John Grace,” a classmate she married in 1920.

Fermano knows this from bits of conversation from her very elegant but very private grandmother. She’s also read Coates’s unpublished memories of the young Hemingway. Coates wrote that the teenage Hemingway was

a great, awkward boy falling over his long feet … in life, a disturbing person with very dark hair, very red lips. Very white teeth, very fair skin under which the blood seemed to race, emerging frequently in an all-enveloping blush. What a help his beard, later was to be, protecting and covering this sensitivity. The whole of his face fell apart when he laughed.

They had “lots of nice times,” Coates wrote, “skating, walks, movies and opera.”

Also in the document are descriptions of Hemingway’s mother (“A big, majestic woman … [who] moved as a ship does, with great majesty and authority”) and a biting assessment of Hemingway’s personality (“The inferiority complex remained to the end and with it came the braggadocio and the need to become somebody to himself … a quick and deadly jealousy of his own prestige and a constant … and consuming need for applause”).

Fermano never thought that anyone would want letters almost a century old that Hemingway had written to an unknown classmate. Coates and Hemingway shared proximity on the staff of their high school literary magazine, the Tabula, where Hemingway was a contributor and she was the music editor. She was a year older than him, a senior when he was a junior.

Coates herself was a discreet figure. Though she’d become a successful local opera singer who was used to being featured in the press, she didn’t publicize her connection with Hemingway, and she was hesitant to talk about it—even when approached by the author’s first biographer, the Princeton University professor Carlos Baker, in 1963 and again in 1966. She was reluctant to add to the cult of Hemingway that had sprung up, and remembering those years in Oak Park was trying—Coates’s mother was sick then, and had died young.

Baker does, however, mention Coates in a single, powerful paragraph that traces Hemingway’s infatuation with her to an April 1916 performance of Martha, a three-act high school opera. On stage, Coates played a huntress in the chorus and “Third Servant.” Baker writes: “Playing his cello in the orchestra pit, Ernest could hardly keep his eyes on the score. His friend Al Dungan, a gifted cartoonist, made a caricature of a boy with desperate eyes and labeled it: ‘Erney sees a girl named Frances.’ He was too shy to ask her to the Junior-Senior prom on May 19.”

In an undated, unsent letter written after the book’s publication, Coates thanks Baker for an insight: “I never understood, until reading your book, [Hemingway’s] bitter remark when I told him John and I were engaged: ‘All the good girls are taken!’ ”

Two decades later, Hemingway may have aired some of his bitterness in To Have and Have Not. Reading the novel, Frances recognized broad caricatures of herself and John, who attended the University of Wisconsin and became a successful railroad executive—especially when Hemingway tells of a young man sworn into an elite, Ivy League secret society:

The fiancé is a Skull and Bones man, voted most likely to succeed, voted most popular, who still thinks more of others than of himself and would be too good for anyone except a lovely girl like Frances. He is probably a little too good for Frances too, but it will be years before Frances realizes this, perhaps; and she may never realize it, with luck. The type of man who is tapped for Bones is rarely also tapped for bed; but with a lovely girl like Frances intention counts as much as performance.

Coates couldn’t miss the note of resentment in it: “I went to the Country Club dances with John, rode in his father’s high and shiny Packard car, as I realize how it must have seemed to Ernie (one doesn’t sense those things when one is young).”

Hemingway’s mother seems to have admired Coates as much as he did. In her family scrapbook, Mrs. Hemingway underlined Coates’s name in the program from the opera where she first caught the young Hemingway’s eye. Next to it, she wrote: “The most graceful, dainty and charming girl on the High School stage. She is adorable … ”

At least one letter from Coates to Mrs. Hemingway survives in the Harry Ransom Center in Austin. In May of 1924, Coates writes: “the gift of your friendship and sympathy is one that I have treasured thru the years.”

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Coates’s documents pose a few new mysteries. She references other letters that Hemingway wrote her from Kansas City, where he worked as a reporter for the Kansas City Star before he volunteered for the Red Cross. That correspondence has never been recovered—nor has a letter to Coates from his sister Marcelline, in which she blames Frances for her brother’s running off to volunteer for the American Red Cross. If Coates had returned his affection, Marcelline implies, Hemingway might have seen fit to stay put.

Marcelline was working the other side, too: she never discouraged Hemingway from pining for Coates, even after her engagement. In a letter dated July 5, 1918, Marcelline wrote Hemingway in Italy: “I suppose you heard … Frances Coates & Jack Grace are engaged? It was announced the day after you left ! (Wise Frances!)” The next month, on August 25, she added: “In my previous letters I told you about Frances Coates’ engagement to Jack Grace, but I’ll tell her to write you anyway. She isn’t wedded yet, y’know.”

As for Hemingway and Coates themselves, the last surviving letter between them was from Coates, in January of 1927, when Hemingway’s first son, John, was three, and—unbeknownst to Coates—his marriage to his first wife, Hadley, had broken down.

“I just finished The Sun Also Rises and you are before me so vividly that I must tell you how much I enjoyed the book,” she writes, calling the novel “heartbreaking.” She continues: “The years are making you a strange person—I should so love to see you—I haven’t seen Marce for over a year—but someone said you were returning. I have a ravishingly beautiful daughter to match your son—and I’d so like meeting your nice Hadley … Jack joins me and wanting to see you both.”

Fermano doesn’t know if Hemingway responded, or if they ever saw each other again.

Her grandmother, despite the nostalgia that comes with such keepsakes, was clearly happy with her choice. Frances and John were married for sixty-seven years. They raised a daughter, traveled the world, and died a year apart, in 1988 and 1989. On the front of the envelope containing her photos with Hemingway, Coates wrote: “Ernie Pictures / And 25 years later ooh! Am I glad I married John.”

Robert K. Elder (@robertkelder) is the coauthor of Hidden Hemingway: Inside the Ernest Hemingway Archives of Oak Park. He’s the author of six other books and director of digital product development and strategy at Crain Communications.

All photos courtesy of the author, except where noted.