The Connoisseur of Desire | Andrew Delbanco | The New York Review of …

22-27 minutes 5/8/2025

Reviewing The Notebooks of F. Scott Fitzgerald in these pages forty-five years ago, Gore Vidal called him a “bold chronicler of girls who kissed.”

Apart from the unwarranted condescension, the point was fair enough. Fitzgerald wrote frequently and fervently about boys dreaming of kissing a girl or recollecting the thrill of it, or relinquishing the hope of it, or, upon achieving it, asking themselves, “Had she been moved?… What measure of enjoyment had she taken in his kisses? And had she at any time lost herself ever so little?”

Here, from his first novel, This Side of Paradise (1920), is the first kiss between Amory Blaine, a “young egotist” fresh out of Princeton, and Rosalind Connage, a girl with an “eternal kissable mouth” who’s been expelled from Spence for an infraction that she can’t, or won’t, remember:

HE: But will you—kiss me? Or are you afraid?

SHE: I’m never afraid—but your reasons are so poor.

HE: Rosalind, I really want to kiss you.

SHE: So do I.
(They kiss—definitely and thoroughly.)

HE: (After a breathless second) Well, is your curiosity satisfied?

SHE: Is yours?

HE: No, it’s only aroused.

Then a coy stage direction (“He looks it”) invites the reader to decide whether Amory’s arousal reveals itself as a facial flush or an evident erection.

Fitzgerald’s second novel, The Beautiful and Damned (1922), includes a chapter called “The Connoisseur of Kisses” that categorizes kisses by motive and effect. Some burn fiercely before “the flame retreats to some remote and platonic fire.” Others are cool from the start, as when a college boy presses himself upon a trusting shopgirl who, “after half a dozen kisses,” expects a proposal but gets at most a trinket before he moves on to his next adventure. Then there are young women who, with the nonchalance born of money, “kiss a man beautifully and romantically without any desire to be either his wife or his mistress.” In this gallery of portraits, Fitzgerald brought special conviction to those of earnest young men—no doubt partly self-portraits—fumbling to express “the most inept intimacy” with young women who kiss them casually as a form of recreation. This kind of mismatch furnished the plot for several early stories published in Redbook, McCall’s, and other mass-circulation magazines and later collected under the summary title All the Sad Young Men (1926).

Adolescent mouth-to-mouth action might seem an unpromising subject for a serious writer. But in the America of Fitzgerald’s youth—he was born to Catholic parents in St. Paul, Minnesota, in 1896—sexual life was still tightly regulated, and the idea of writing about young people taking tentative steps toward intimacy with commingled breath and lips touching lips was daring in a way that’s difficult to grasp in our age when teens are connoisseurs of pornography. An array of strong forces—school (Fitzgerald attended a Catholic prep school), church (he briefly aspired to the priesthood), and family (his mother refused to venture during her honeymoon into the naughty streets of Paris)—rallied around the conviction that sexual desire, as D.H. Lawrence put it with rage and sorrow in Sons and Lovers (1913), must be “suppressed into a shame.”

Soon after leaving college, Fitzgerald declared to his Princeton friend Edmund Wilson that “I want to be one of the greatest writers who ever lived, don’t you?” Inspired by Lawrence as well as by such older American contemporaries as Booth Tarkington, Sherwood Anderson, and Willa Cather, he set out to write about young people vibrating between excitement and anxiety at the first intimations of a breach in their sexual restraint.

But moving east didn’t take him all that far from the norms of his native Midwest. Most of his classmates remained unwillingly chaste. In response to a senior-year survey, barely half the class of 1917 (Fitzgerald matriculated with that class but never graduated) claimed ever to have kissed a girl. As for those who answered with an honest “yes,” they knew that nothing much more than a kiss could be expected from the sort of “nice” girls they encountered in New York or New Haven or, in Fitzgerald’s case, at holiday sledding parties back home. Like many young men of his caste, he had his sexual initiation with a prostitute when, at age twenty in the spring of 1916, for “the first time…I hunted down the spectre of womanhood.” Years later Dick Diver in Tender Is the Night (1934) recalls with lingering frustration his Yale days, when “the young maidens…kissed men saying ‘There!,’ hands at the man’s chest to push him away.” In that same book we find Dick’s wife, Nicole, begging the half-French mercenary Tommy Barban:

“Kiss me, on the lips, Tommy.”
“That’s so American,” he said, kissing her nevertheless. “When I was in America last there were girls who would tear you apart with their lips, tear themselves too, until their faces were scarlet with the blood around the lips all brought out in a patch—but nothing further.”

Throughout his writing life, Fitzgerald’s animating theme was the sweet torment of “nothing further.”

The book that proved him to be more than a minor writer about frat boys and flappers was published one hundred years ago, when he was not yet twenty-nine. Initially conceived as a story with a “catholic element” set in the Midwest and New York in the 1880s, The Great Gatsby had several false starts. Fitzgerald jettisoned large portions of early drafts but salvaged some material for use in freestanding stories. He rewrote numerous passages and, with the indulgence of his editor, Maxwell Perkins, extensively reworked the galley proofs just weeks before the scheduled publication date. In a preface to the annotated centennial edition published by the Library of America, the eminent textual scholar James L.W. West gives a valuable account of the evolution of The Great Gatsby from germinal idea to finished novel, carried along by the author’s determination, in West’s words, “to bring it as close to perfection as he could.”

It was published on April 10, 1925, to good reviews but disappointing sales. Two months later Fitzgerald wrote to Perkins suggesting jacket copy for the collection of stories (All the Sad Young Men) that Scribner’s planned to bring out that fall on the heels of the novel:

Show transition from his early exuberant stories of youth which created a new type of American girl to the later and more serious mood which produced The Great Gatsby and marked him as one of the half dozen masters of English prose now writing in America.

Perhaps abashed by his own self-praise, he assured Perkins that the blurb could be “toned down as you see fit.”

In fact he had no reason to retract it. One of the early reviewers, Gilbert Seldes, marveled at the “intense life” with which Fitzgerald rendered “crowds and conversation and action and retrospects” and agreed that he had “mastered his talents and gone soaring in a beautiful flight.” The new book should “be read, the first time, breathlessly,” as it sends everything, animate and inanimate, into exuberant motion. Outside Tom and Daisy’s house the lawn “ran toward the front door for a quarter of a mile, jumping over sun-dials and brick walks and burning gardens”; inside, “two young women were buoyed up as though upon an anchored balloon…their dresses…rippling and fluttering as if they had just been blown back in after a short flight around the house.” Across the bay, at Gatsby’s parties, there’s also perpetual movement, but it feels more frantic than ebullient—couples dancing to the “tinny drip of the banjoes on the lawn…old men pushing young girls backward in eternal graceless circles,” or “superior couples holding each other tortuously, fashionably,” locked in solitude despite their bodies converging and diverging under “the premature moon, produced like the supper, no doubt, out of a caterer’s basket.” Fitzgerald was acutely observant of manner and style in his major and minor characters and equally attuned to the veiled disquiets of their inner lives. He had accomplished something uncommon in fiction: a work of social realism from which there emanates a shimmer of allegory.

The Great Gatsby tells the story of a lowborn midwesterner, Jimmy Gatz, taken under wing by Dan Cody, a man of equally inauspicious origin reared in “the savage violence of the frontier brothel and saloon,” who, having made a fortune in mining, cruises on his trophy yacht with Jimmy aboard as aide and protégé. Young Gatz eventually makes his own fortune in the bootlegging business and, mimicking his mentor’s self-invention, transforms himself into Jay Gatsby, a putative Oxford man (“All my ancestors have been educated there”) on the shore of Long Island Sound in a huge faux-Norman chateau, “spanking new under a thin beard of raw ivy,” with a portrait of Cody hanging on his bedroom wall.

But before the transition was complete, he had enlisted in the army and was assigned to a training camp near Louisville. There, magnetic and extravagantly handsome, he courted a much-pursued Kentucky belle, Daisy Fay, whose voice was “a singing compulsion, a whispered ‘Listen,’ a promise that she had done gay, exciting things just a while since and that there were gay, exciting things hovering in the next hour.” Allowing this beautiful siren to believe that he, too, was highborn, Gatsby succeeded in seducing her. At first his motive was the usual hunt for transient pleasure, but while awaiting deployment to war, as “she brushed silent lips against his coat’s shoulder or when he touched the end of her finger, gently, as though she were asleep,” he discovered that he loved her—insatiably, irredeemably—and that she nourished him with “the incomparable milk of wonder.”

This twice-transformed man returns after the Armistice to discover that on the rebound from their affair Daisy has married a more socially suitable suitor—Tom Buchanan, a rich, stupid, thuggish Chicagoan with a Yale pedigree. But Gatsby is desperate “to recover something, some idea of himself perhaps, that had gone into loving Daisy” and so becomes what in today’s idiom would be called a stalker.

All this is told in flashback. The narrative of Gatz-Gatsby’s pursuit of Daisy—recounted by her cousin and Tom’s college classmate, Nick Carraway, an unambitious bond salesman who rents a cottage on the edge of Gatsby’s estate—begins four years later, in the summer of 1922. In the intervening years Gatsby has become a considerable gangster, but he has a countervailing gentleness that’s not wholly a pose; his love for Daisy, acquisitive and vain, also has a dazed reverence that borders on piety. Fixated on the dream of recovering her, he establishes himself in impressive grandeur across an inlet from the Buchanan mansion, at which he stares with mixed yearning and revulsion. He’s been obsessed with retrieving Daisy for “so long, dreamed it right through to the end, waited with his teeth set, so to speak, at an inconceivable pitch of intensity.”

The Great Gatsby is an intensely erotic book. But it carries Fitzgerald’s favored theme of “nothing further” far beyond the erotic life narrowly construed and into the universal experience of obstructed longing. Consider Jay and Daisy’s first kiss:

His heart beat faster and faster as Daisy’s white face came up to his own. He knew that when he kissed this girl, and forever wed his unutterable visions to her perishable breath, his mind would never romp again like the mind of God. So he waited, listening for a moment longer to the tuning-fork that had been struck upon a star. Then he kissed her. At his lips’ touch she blossomed for him like a flower and the incarnation was complete.

The writing here, verging on purple, recalls William James’s account (Fitzgerald had read James after college) of religious ecstasy as a “marvelous and jubilant…sense of renovation…as if an extraneous higher power had flooded in and taken possession” of the believer. But what Gatsby yearns to feel again is not “the incarnation…complete.” It’s the wild anticipation he felt in the instant when, to the pounding of his heart, her “face came up to his” for the first time.

Soon after the transfiguring kiss, he “took” her “ravenously and unscrupulously”—an act he would undo in his retrospective imagination. It’s the virginal, bridal Daisy of whom he dreams. She is to him the immaculate lady of the troubadour songs of courtly love, or Goethe’s Lotte, who tells her fated lover in The Sorrows of Young Werther—the urtext for all Fitzgerald’s stories of sad young men—that “it’s only the impossibility of possessing me that makes you want me so much.”

Lionel Trilling once described The Great Gatsby as a book filled with “tenderness toward human desire.” Maureen Corrigan, in her delightful So We Read On: How The Great Gatsby Came to Be and Why It Endures (2014), says that “wanting…runs through every page.” It is indeed an almost concupiscent book brimming with desire—not only Gatsby’s for Daisy but Nick’s for the illicit promise of New York by night, Tom’s for any rush of pleasure to match his college football glory days, Myrtle Wilson’s (Tom’s current mistress) for release from her ashen life, Jordan Baker’s (the louche woman who vaguely wants to sleep with Nick) for desire itself.

For Fitzgerald, the electric shock of desire is always strongest just before the circuit is closed. The theme of delicious anticipation runs through everything he wrote, from the portrait of young Amory (“It was always the becoming he dreamed of, never the being”) to the account in his essay “My Lost City” (1932) of New York radiating “all the iridescence of the beginning of the world.” When, from the observation deck of the newly opened Empire State Building, he sees that the city “had limits,” the discovery fills him with dread. In The Great Gatsby, everything seems in motion, but the movement tends toward depletion, the keynote always the imminence of the end, as with Daisy’s voice, “the kind of voice that the ear follows up and down, as if each speech is an arrangement of notes that will never be played again,” or the ephemeral glow of evening light as it fades from her face, “deserting her with lingering regret, like children leaving a pleasant street at dusk.”

This dread of endings—the end of youth, of frolic, of love, of life itself—was one reason Fitzgerald resorted with such lust to alcohol, by which he could compress past, present, and future into one rapturous moment that felt impervious to time. “The drink,” he writes in Tender Is the Night, “made past happy things contemporary with the present, as if they were still going on, contemporary even with the future, as if they were about to happen again.”

Fitzgerald has been aptly called our “prose Keats.” He loved the great odes—compared with which most other poetry struck him as “only whistling or humming”—especially “Ode to a Nightingale” (from which he drew the title for Tender Is the Night), in which the “light-winged Dryad of the trees” soars and sings in joyous flight above the scene below, “Where youth grows pale, and spectre-thin, and dies;/…Where Beauty cannot keep her lustrous eyes.” This craving to arrest the relentless process of loss and decay suffuses Fitzgerald’s prose as much as Keats’s verse. Reading his notebooks (his biographer Matthew Bruccoli calls them his “workshop”) is like overhearing a musician improvising while practicing for no audience but himself. We listen in as he tries out images and phrases for expressing desire intensified by foreknowledge of its evanescence—as when prospective lovers approach each other, moving closer, leaning in, delaying contact in order to prolong the exquisite tension of the penultimate moment:

A few little unattached sections of her sun-warm hair blew back and trickled against the lobe of the ear closest to him, as if to indicate that she was listening.
Her face, flushed with cold and then warmed again with the dance, was a riot of lovely, delicate pinks, like many carnations, rising in many shades from the white of her nose to the high spot of her cheeks. Her breathing was very young as she came close to him—young and eager and exciting.
She kissed him several times then in the mouth, her face getting big as it came up to him, her hands holding him by the shoulders, and still he kept his arms by his side.

Fitzgerald was always hoping to preserve hope before it subsided into experience.

This was Keats’s theme in “Ode on a Grecian Urn,” whose painted lover is frozen in the “wild ecstasy” of perpetual pursuit:

Bold lover, never, never canst thou kiss,
Though winning near the goal yet, do not grieve;
She cannot fade, though thou hast not thy bliss,
For ever wilt thou love, and she be fair!

With Jay Gatsby, Fitzgerald embodied this inextinguishable desire in a figure who is relentless, deluded, but immensely attractive all the same. He’s an impostor and a con man yet somehow not a phony or a liar. He brings a radical, even noble fidelity to “the colossal vitality of his illusion,” at the center of which is always and only Daisy, about whom one imagines him singing like Keats’s discarded lover in “La Belle Dame sans Merci”:

I met a lady in the meads,
Full beautiful—a faery’s child,
Her hair was long, her foot was light,
And her eyes were wild….
And there she lullèd me asleep,
And there I dreamed—Ah! woe betide!—

The latest dream I ever dreamt
On the cold hill side.

When at last Gatsby is startled awake from his dream, Fitzgerald delineates with great compassion the agony of his recognition, and his simultaneous refusal to believe, that Daisy will never rejoin him.

Soon after publication, sales of The Great Gatsby dried up. Four months before Fitzgerald died of alcoholism and heart disease in December 1940, the last royalty statement he saw reported seven copies sold in the previous year. After his death it got a second life when it was issued in 1945 as an Armed Services Edition (155,000 copies printed), perhaps on the premise that GIs abroad would be drawn to the story of a soldier carrying the torch for a girl back home. Beginning in the 1950s it became a staple of high school and college reading lists and has since sold in the tens of millions.

Among major American novels it must hold the record for bad adaptations. The competition began almost immediately, with a 1926 stage version by Owen Davis, whom Fitzgerald called with wry contempt “the king of proffessional [sic] play doctors.” Later that year Paramount released a silent film based on the play, starring Warner Baxter as Gatsby (before he became famous as the Cisco Kid).

After the Armed Services Edition gave the book a second wind, a parade of heartthrob actors lined up for the role. First came Alan Ladd in 1949, then Robert Redford in 1974, and most recently Leonardo DiCaprio in Baz Luhrmann’s 2013 costume spectacle, with significant changes in the plot. (A 2000 TV version cast its leading man, Paul Rudd, in the role of Nick.) All these films—except for the Alan Ladd version, which has a brisk film noir pace—are talky and stodgy, with the predictable feel of a period piece.

Two musical versions have lately reached the stage—The Great Gatsby on Broadway and Gatsby: An American Myth at the American Repertory Theater in Cambridge, both with lavish sets populated by gyrating dancers and humping couples (including Jay and Daisy) and, in the latter case, an enhanced role for Myrtle Wilson, whose adultery is treated empathetically as her effort to escape her grief for a lost child. Much closer in spirit to Fitzgerald’s book is Elevator Repair Service’s eight-hour full-text reading, Gatz, which forces the audience to concentrate on his words in the context and sequence in which he wrote them.

Five years ago Parul Sehgal offered a lively survey (with no claim to be exhaustive) of “Fitzgeraldiana,” which by then included young adult and mystery novels, prequels and sequels, and even a Taylor Swift song.

Among Gatsby-inspired writers, she rightly singled out Joseph O’Neill for his beautifully wrought novel Netherland (2008), set in post–September 11 New York and narrated by a wounded man in a wounded city who’s drawn, like Nick to Gatsby, to a charming gangster “cheerfully operating in the subjunctive mood.” Guided by his motto to “think fantastic,” this “willful, clandestine man” steps in one scene onto a gravestone marked “DAISY” and ends up a corpse not in a swimming pool but, with his hands bound, in the industrial stew of the Gowanus Canal.

Now in its centennial year, The Great Gatsby seems likely to remain a touchstone of our culture at least for a while. Among canonical authors Fitzgerald has so far been spared from fatal chastisement for barely making room in his fiction for people without club memberships or trust funds. Black people flicker by in the background as exotics. Gay people seem menacing. Jews are sly and slithery, most famously Gatsby’s business partner Meyer Wolfshiem, the canny gambler who wears human molars as cufflinks. (One of Fitzgerald’s best readers, Arthur Krystal, calls his antisemitism “provincial but not malicious.”) As for women, they are assessed almost entirely through male eyes. Even Daisy is less a fully drawn character than a projection of Gatsby’s imagination as he feeds on the “incomparable milk of wonder” with which she nurses his narcissism.

But Fitzgerald was far more dismissive, even savage, about the self-adulatory country-club set, as in his portrait of Tom Buchanan, who is cruel to women (both Myrtle and Daisy) and warns with odious sanctimony that “if we don’t look out the white race will be—will be utterly submerged” in the coming flood of miscegenation. Fitzgerald had measureless contempt for “careless people” like Tom, and ultimately for Daisy, who “smashed up things and creatures and then retreated back into their money…and let other people clean up the mess they had made.”

Back in 2020, with her eye on the inscrutable future, Sehgal asked, “What other waves of analysis await us as the new narratives rush in?” Since then The Great Gatsby has continued to be read as, among many other things, an indictment of Jazz Age decadence, a parable of overreaching, a study of gender dynamics, a tale of old money triumphing over a parvenu, and an account of unconscious homoerotic desire—in one way or another, a modernist rebuke of the hollow mendacity of the American Dream. Most recently, it supplied the title, Careless People, for Sarah Wynn-Williams’s best-selling takedown of Meta (formerly Facebook).

But first and last, The Great Gatsby is a story of unrequited love that invites rereading or even reciting, as poetry does when there’s too much music in the words to be absorbed in a single listening. However counterfeit Gatsby may sometimes seem, there is, as Nick says, “something gorgeous about him,” something ingenuous in his “extraordinary gift for hope.” And so the sadness is fierce when, forced at last to relinquish his imperious dream, he “looked up at an unfamiliar sky through frightening leaves and shivered as he found what a grotesque thing a rose is and how raw the sunlight was upon the scarcely created grass.” The story of this man—once brazen, now bereft—is told with such ravishing prose that he must have merged again in Fitzgerald’s imagination with Keats’s broken lover, stranded where “the sedge is withered from the lake,/And no birds sing.”