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Ring Lardner told his friend F. Scott Fitzgerald that Fitzgerald’s 1926 novelette “The Rich Boy” should have been expanded into a novel. Fitzgerald didn’t see fit to augment it, but three-quarters of a century later, Caitlin Macy did in her impressive, if derivative, first novel, The Fundamentals of Play.

A few critics have drawn comparisons between Macy’s book and Fitzgerald’s The Great Gatsby, which was being prepared for publication as he wrote “The Rich Boy.” It’s true that Macy’s Harry Lombardi can be considered an ingenious Internet Age Gatsby. But in Macy’s tale of obsessive love, the more meaningful parallel is to “The Rich Boy.”

Fitzgerald’s rich boy is Anson Hunter, a genial Jazz Age preppy-turned-Yalie who drinks too much and plays cards. Hunter is a stockbroker whose heart is broken by a onetime fiancée, Paula, whom he met on the coast of Florida. Hunter, in turn, breaks the heart of a later amour, Dolly, then goes on to indulge in shallow affairs even as he interferes in the affairs of others, casually destroying a few lives.

In The Fundamentals of Play, the role of Hunter (connotation intended) is filled by Kate Goodenow, a genial Gen-X preppy-turned-Yalie who drinks too much and plays cards. Kate is a Sotheby’s expert on American paintings whose heart was broken by her high school sweetheart, Nick Beale, whom she met on the coast of Maine—or at least by the circumstances of his leaving her. She, in turn, breaks the hearts of two fiancés, Chat Wethers and the above-mentioned Harry. Kate eventually marries, but only after interfering in the affairs of others, casually destroying a few lives.

In Fitzgerald’s story, the nameless narrator is moneyed enough to track Hunter’s whereabouts but unmoneyed enough to observe Hunter’s behavior with a certain distance—equal parts envy and disdain. In Macy’s story, the narrator has a name, George Lenhart, but the other characteristics apply.

So the plots have similarities, right down to their denouements, that appear more than coincidental. The Town Club, the highballs, and all the yachting and private-school talk in Macy’s book echo Fitzgerald’s story like Gershwin tunes from a ghostly piano. But what really centers Macy’s episodic novel on Fitzgerald’s novellete is “The Rich Boy”‘s oft-misquoted pearl: “Let me tell you about the very rich. They are different from you and me. They possess and enjoy early, and it does something to them, makes them soft where we are hard, and cynical where we are trustful….”

For all Macy’s implicit borrowing, she doesn’t refer to that quote, probably because it would be too obvious a key to her literary source. Nonetheless, the passage speaks to The Fundamentals’ fundamental tension: whether that indictment of the wealthy by “The Rich Boy”‘s narrator is true.

Initially, Macy’s George thinks not. “I had always believed that my own upbringing had been just like theirs, like Chat’s or Kate’s, that except for the money we had been raised in just the same way,” he says. If the money makes any difference, George explains, it’s that it gives the Kates of the world a carefree grace. “There was no promise in Kate’s laughter; in fact it was just the opposite note that seemed to resound, an expression of utmost faith in today, of total absorption in the moment as it passed. ‘You know, George, the main thing is to have fun,’ she asserted.” Later, George says, “With Kate I was forever trying to live up to an ideal, but when you considered what that ideal was, it made no sense at all, my striving: it was an ideal of carelessness.”

Inconveniently, George cares. A budding broker, he cares about money. His father is the headmaster of a private school and the tattered if not desperate scion of a “name” family that had the gall to lose its fortune. Worse still, George cares about Kate, and he wishes to hell he didn’t. “My own ambition for Kate suddenly seemed vulgar…” he says early on, “like a bold, alcohol-induced comment that one would never make sober.”

As George learns, Kate the carefree princess has cares of her own after all, most of which find their expression in her longing for the lost Nick. Nick is a tanned, stoned boy beauty who, thanks to his natural sailing talents, literally bobs up and down between social strata. He is, by both type and analogy, the laconic Brad Pitt to Kate’s fragile Gwyneth Paltrow.

If Kate is obsessed with Nick, Harry is equally bewitched by Kate. George and the thoroughbred prepster Chat chatted about Kate at Dartmouth freshman year—George knew her from school, Chat from the Bar Harbor boating set. Little did they know, as they sifted through their Kate trivia, that Chat’s intriguing misfit roommate, Harry, was taking the information in with the same spooky, reflexive ease with which he counted cards and shot the moon the first time he played Chat and George in hearts.

While drinking Chat under the table, Harry apparently grilled him on further, arcane Katiana when the two met up working in China. Back in the Big Apple, when Chat’s away, Harry applies his knowledge of Kate to the fundamentals of social play in a new, vertiginous league, the same way he boldly applies his casually soaring computational and business skills to a mysterious novelty called the Internet.

Kate lives up to her motto and has her strangely joyless fun—about which, we find, she is deadly serious. And it seems intertwined with an almost Darwinian quest for an appropriately prosperous mate. Female competitors—particularly Harry’s once-and-again girlfriend Cara—are no match for the kind of social venom that can be produced only by generations of inbreeding on the Upper East Side.

This is, if you’ll pardon the expression, rich material, and Macy plays her authorial hand well. Brief, mysterious allusions to Kate’s origins are made by a soused relative at a Goodenow party. And Harry apparently had to get Chat out of a scrape in China involving Chat’s untoward advances toward a young woman—an episode indicating a possible dark side to Chat’s sexuality beneath his oh-so-casual unflappability. Also tantalizing are hints that Kate might be closer to wit’s end than Land’s End, suffering, perhaps, from depression and frigidity.

Macy, like filmmaker and novelist Whit Stillman, also manages to balance the silliness and poignancy of society talk. We can’t quite take it seriously; and we can’t dismiss it, either, as in this telling dialogue:

“They should never have let women into the Town Club,” said Chat gloomily.

“Oh, have they?” I said. I meant this to be ironic somehow—as if I would know the inner workings of the admissions policy—but the irony was lost on Kate.

“Well, not really,” she said seriously. “Only till we’re thirty.”

“Then what?”

“Then we have to marry in or we’re out.”

“Put out or shut out,” they both said, and they both gave half a laugh.

Macy’s descriptive powers and keen ear aren’t limited to the Poppy and Muffy dockside clique, either. In fact, Chat and George’s visit to see Nick, his decidedly inelegant sister, Deb, and her baby girl in East Haven has some of the novel’s best moments.

But the problem with sparring with Fitzgerald is that, ultimately, you’ll lose. Though Macy goes more rounds than would most young authors, she is eventually pinned to the ropes by her own late-breaking plot contrivances and character shortcuts. For instance, Harry’s conservative Catholicism, which becomes oddly important, just doesn’t fit. Nor does Cara’s morphing from aerobicized party girl in leggings to conniving temptress. Perhaps these machinations wouldn’t stand out in such unflattering relief were not George’s narrative generally so much subtler. Fitzgerald acknowledged that part of his trade-magazine formula was “a touch of disaster,” but he camouflaged the technique better than Macy. CP