High Society:

“Darling, I can love you better. I promise.”

“Get your filthy hands off of me, Charles. You’re lucky half of New England is here or I’d divorce you right now.”

“Honey, please—”

Tyler surveyed the hosts’ hissed quarrel lazily over the rim of his champagne. It wasn’t a party without Mr. Baudelaire getting caught pawing at a lithe, blonde waitress while his spouse imbibed five too many martinis, and proceeded to erupt like a menopausal Mount Vesuvius, to the scandalized murmurs of the mob of trophy wives ready to devour the fresh gossip material that they’d regurgitate over Sunday brunch. Half of the guests only showed up to these little country club soirees to watch these showdowns, Tyler not included. If he wanted to tune in to the petty quibbles of the elite, he could do so from the comfort of his crocodile leather couch, and maybe even catch the bone china his parents hurled at each other when they’d exhausted every curse word they knew.

That very morning they had smashed through the last of their antique tea sets, but now the Westleys hovered near the oysters, schmoozing some Manhattan socialite and nautical lawyer, regaling them with fabrications of “the lovely weekend they had out on the Cape,” and having a subtle “my-yacht-is-bigger-than-yours” pissing contest. Even a couple of Xanax later—for his “anxiety”—seeing their happy couple dance, featuring trademark moves like Mother clutching her pearls and laughing airily and Father patting her shoulder like a bear having a seizure, made Tyler viscerally ill. 

The sea of pastels saturating the practically blinding marble courtyard only added to Tyler’s growing migraine. The partygoers wafted about haphazardly, swatches of shift dresses and suits in bourgeoise colors like Nantucket Red and Carolina Blue alternating between orbiting around the open bar and each other, but never lingering longer than a generic jazz song churned out by the orchestra. Somewhere a toddler in a unnecessarily expensive designer suit let out a wail. 

Tyler twiddled his monogrammed cufflinks, before letting his gaze fall somewhere over the pale glow of the horizon, contemplating the inexhaustible soul-crushing boredom afforded only by the ludicrously wealthy: the purposeless existence of the privileged. He was a Dartmouth man, just as his father had been, and his grandfather before that, and soon enough he’d breeze through Harvard law school, out of tradition more than necessity, and take up the mantle at the family firm. There was nothing more for him, but to act out the script of the perfect White-Anglo-Saxon-Protestant life floating from country club to yacht club, from the Hamptons to Martha’s Vineyard before inevitably turning to liquor or mistresses or hard drugs to fill the gaping hollow where meaning should be. 

The sight of a figure clad in an identical Brooks Brother suit sashaying a path through the masses shook Tyler out of his melancholia. The man bounded up the stairs to join him on the marquee, lolling back against the banister beside him, drink in hand. 

“Hola.” Kelly slid Tyler a fat alligator skin pouch by way of greeting. “Good haul today.”

“I’d say,” Tyler said, producing a Rolex from his khaki pockets, before checking the time on his own. “And it’s still early.”

They’d perfected their craft over the years, the hours of relentless ennui imprisoned in the ivy-and-brick confines of boarding school giving them ample opportunity to train themselves to wade through the pretentious muck of old money and sniff out the fake Prada bags from the genuine Cartier wedding bands. They started with hockey sticks from their team’s locker room, then targeted their dorm parent’s marijuana stash, then it was the liquor store a couple towns over, and then their crowning glory: the Pyramid scheme that spanned the entire prep school community and resulted in over a hundred expulsions; however, Tyler and Kelly still graduated cum laude with smiles on their faces and even more money weighing down their trust funds. They’d donated it all to the Red Cross.

With Tyler’s All-American boyish charm, perfectly parted blonde hair and prep school drawl that rolled words like “conundrum” and “inadvertently” off his tongue like shredded autumn leaves, no one ever suspected him of getting his lily-white hands dirty. Kelly looked a little more culpable, especially to the elder and inherently more racist generations: his year-round tan and the excess of vowels in his last name lumping him closer to the country club’s pool boy crowd. But since his family owned half of America’s oil industry, people kept their prejudices to themselves. 

A group of Dartmouth alumni stopped to congratulate Tyler on his big lacrosse win, sparing Kelly only withering glances. 

“Go Big Green,” Tyler intoned, his rehearsed response. 

“They don’t like me,” Kelly said ruefully. Who could blame them? He was siphoning off the last of their offshore accounts as they shuffled by. “Oh hey, did you hear Ames is here?”

“His first appearance in high society since he got kicked out of Exeter,” Tyler noted. Their former disgraced classmate skulked by the fountain, while his parents tried to assure everyone that he’d “cleaned himself up” and the sexual assault charges were “never proven.” 

“I wonder if he still wears that massive ring,” Kelly mused with a wicked grin. “I’m gonna go say hi. Maybe shake his hand.”

With Kelly’s departure, Tyler slumped back into silence. A girl caught his eye from across the yard, a bright young thing radiating naiveté, Prohibition-era money, and low self-esteem. She smiled at him, and he smiled back at the colossal diamond chandeliers dangling from both her dainty ears. This was the sort of girl he should marry. The kind he should bring round to his parents who’d laud her family’s name and fortune before they’d all go out on the boat and soon enough have a couple of kids to fill their hauntingly large Greenwich mansion, who’d eventually be shipped off to prep school, and then an Ivy League all for the vicious cycle to start again. The very prospect of that future propelled him to the bar. No one questioned his age, after all, in these parts money got more drinks than a fake I.D.

As the music started to die out and the throngs of revelers began to ebb away, Tyler excused himself to the club’s cobblestone driveway, a bottle of twenty-one year old Chivas and the girl’s earrings poking out of his jacket, with his now-loosened Vineyard Vines tie an idle noose. A black cadillac pulled up in front of him with a honk and a screech of imported rubber.

“I hate when the valet hands me the car. They all look at me like I’m your chauffeur,” said Kelly. 

Tyler edged into the passenger seat wordlessly, and Kelly gunned the engine, laughing at the terrified gasps of the crowd who had just shuffled out of the party. Dixie Chicks blared on the radio. 

“Oh my god, I like, love this song,” Kelly said before miming vomiting and changing the channel to some indie station that Tyler had never heard of. He lit a cigar, balancing it on the hulking, golden “B” monogram of the ring now adorning his hand. Tyler stared out of the dashboard as the smoke swirled and blurred the last of the summer foliage streaking by. They were halfway home and halfway through the whiskey bottle when he spoke up.

“God, we’re in our twenties. We’ve got four times this much longer to live through. I can’t do it.”

Kelly gave him a veiled glance. “I feel you man, but hey, you know what, I think I saw a liquor store back there.”

Tyler perked up in his seat as Kelly reached one hand into the glove compartment, the sky’s dull cerulean-pink blend that heralded the evening and the promise of restless delinquency falling upon a bundle of ski masks and their fathers’ hunting pistols. 

“Do we have to ditch the car again? Nothing says class like a drive-by robbery in a Cadillac.”

“Nothing says convicted like a drive-by robbery in a Cadillac.”

Kelly threw his head back and laughed into the wind. With their faces hidden, windows rolled down, and radio belting out the deranged cello riff of a Vampire Weekend song, they drove off into the dying embers of the sunset, like a yuppie Thelma and Louise.