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Gatsby and Me on Waikiki


By Michelle Railey

The Moana Surfrider: Main Portico

Let me tell you about the very rich. They are different from you and me.”  ~ F. Scott Fitzgerald, The Rich Boy“

I’m in Hawaii on borrowed grace. Red‘s here for work, my dad had extra miles he graciously gave (loaned, for somehow I’ll eventually pay him back) me. In short, it feels rather like I’ve shammed my way into paradise, gate-crashed my way into a vacation I didn’t actually earn. And you know, between never-ending gratitude and delight, there’s also a not inconsiderable sheepish, slightly shame-colored thing we’ll call guilt. I don’t know how or why I am lucky enough to be here and other people are not. Yet here I unfairly am, and I’m mostly exhilarated by it, but the strangest thing happened today and it seems oddly related to shams and shame and inadvertent admissions to extravagance, to questions of money and place and surreal experiences. So…

I swear this really happened.

I found myself in easily one of the most elegant and expensive places I have ever been; a place so beautiful I would have assumed people like me would not be permitted to do more than walk through; a place so exclusive, so tasteful, and so luxurious I can’t imagine the number of Condé Nast publications it’s been in, the number of photo shoots it’s formed the backdrop for. High-class, high-dollar; old, historic, Belle Époque grandeur. And, turns out, the Moana Surfrider will let literally anyone in to the casual beach bar to have a $12 cocktail in swank surroundings.

So I sat at a table with a friend while Red was working. We ordered a drink and basked in the banyan tree, the palms, the Pacific; I took unfortunately fuzzy photographs of architectural details and tropical flowers, shells, and sand artfully arranged in huge crystal vases on marbled mahogany tables among endless white Ionic columns and an equally endless parade of beautiful, society, moneyed sort of brides in equally white couture gowns having their photographs done by professionals lugging column-sized cameras.

And then Alberto (not his real name) walked in and sat at the table next to ours, dripping Gucci and Ferragamo bags, clothed in conspicuous consumption, Prada, aviator glasses and gold. He made a quick costume change at his table, from a military-style coat into a shirt he later informed us was a thousand-dollar Gucci purchase he had made minutes ago just so he could change shirts. He sat alone, was clearly already drunkish, and was having to be cared for by the server, who knew him well and handed him the pair of loafers, also Gucci, which she had been keeping for him in her locker. “You left your shoes here last time.”

He approached our table and asked us, please, to join him on the catamaran he was going on. “Come on, come on the boat with me.” We politely declined. And he left, without shoes, leaving his array of high-end shopping bags, his drink, and his leather bag at his table.

The server explained to us that he had a good heart, had old money, and had two homes on the island. She said he just did that sort of thing, found people and put them on boats with himself, or invited them to drink for the day and well into the night. She said she tried to watch out for him and keep him from harmful, predatory people like the Australian couple who had just recently run up a $700 bar tab for Alberto to pay. She said he was the kind that had to go, go, go and liked to have company and, laying a hand over her heart, was “just so good inside.” She said we should have gone on the boat.

I tweeted I had come across the Waikiki Beach Gatsby and my friend and I finished our drinks. Time passed. Alberto returned from the catamaran just after we had paid our tab. He asked if he could sit at our table and repeated that we should have gone on the boat with him. He still had not remembered his shoes.

He ordered what would have had to have been an inordinately expensive bottle of champagne with three glasses. The server brought him some food— he needed it– and champagne was poured: and uncertain what the correct course of action in the situation was, I averted my eyes, expressed gratitude and took a sip. With a stranger who was, frankly, all lost and restless amiability, and probably prone to being taken advantage of, something it felt like I was doing, through no real fault of my own, just by having been handed a glass of absurdly luxurious champagne and being given a peculiarly imperative look from the server.

So we all three sat there, making awkward conversation as it began to rain, next to the banyan, next to the candles, and the brides, the palms, and the Pacific. With champagne. With Alberto/Gatsby, who said he was a nurse, companion, and secretary to a very wealthy elderly lady with Alzheimer’s. He said he had already money. He had a husband whom he loved and two homes and two fur coats (a sable and a mink) he could never wear because “it’s Hawaii.” He said he didn’t have to work. He said he had known the family forever; had cared for the woman’s husband until he passed and was caring for her until the end and he’d be inheriting her complete estate as well. “She has no family. I take care of everything.” A couple tears dropped down his cheek. He removed the aviators to wipe his eyes. He said all he wanted to do was sleep; he just wanted to sleep but he would settle for blowing off steam and he probably drank too much. He said he wished he could sing.

“You should have come with me on the boat. It’s so blue out there, deep blue. I like to dive off the boat,” he said, “straight down. There’s no bottom. It’s very freeing. It’s the best feeling.”

And so it went, sipping champagne with Alberto/Gatsby: sheepish comments on his part about shopping to make himself happy and how he didn’t care how much anything cost and how ridiculous it seemed; stabs at humor with self-conscious grins alternating with deeply sad statements and tears tracking down his cheeks.

My narrative doesn’t do justice to the afternoon, certainly not to Alberto. There was depth there, I think. There was a good heart there, of that I am also certain. But mostly there was a pained and misplaced soul; able to purchase anything but, to date, peace, wanting and seeking and clearly not finding. Alberto’s palpable, rather raw unhappiness was blinding, in a way: I found myself tongue-tied, wishing I could order him buttered toast and scrambled eggs, knowing these things would not help, not really, but that they were comforting sorts of things for sad and hungry souls who might be chilled from catamaran dives and sudden, misty, November Hawaiian rain. I kept pulling my eyes down because it felt indecent to look into a stranger’s face and see such tears, such things; an invasion of privacy accompanied, in a supremely surreal twist, by sips of celebratory champagne. I regretted thinking of fictional, literary Gatsby in connection with this very real human being with very real feelings, very real loneliness.

I hoped the company of my friend and I at least gave Alberto some temporary comfort but imagine it was no different than any other of these days for him: another day, another drink, another batch of strangers to temporarily, quixotically befriend. Simple distraction: transient, anonymous, and interchangeable. Not unlike his luxury shopping, which he described in detail. No judgment here, truly, but I’d place a glass of champagne on a bet that the ink hasn’t dried on the AmEx receipt of any given purchase before the happiness he derived from it has dissipated completely.

I stepped away from the table and when I returned, Alberto was on his way out. He was being gently guided by a concierge as well as the server. He still hadn’t put his shoes on, but he had at least remembered his many shopping bags. He shook my hand. He said he wanted more than anything to go and sleep and so he was leaving. I said that it was understandable and that sleep sounded like a good idea. I asked if I could give him any money towards the champagne (a gauche and probably insulting thing to do, I’m sure). He declined. He put an arm around my shoulders, briefly, and said “Aloha.” I said “Thank you. I hope you find happiness” (I’m socially awkward with a chronic case of pedestrian-mouth and was under the influence of half a glass of Faustian champagne). That’s what I meant but it’s not normally the type of thing one says out loud, you know? I was on my way to saying something else and somehow those are the words which horrifyingly, embarrassingly tumbled out of my mouth. But there it was and I did my best. He said thank you again and his train of discreet and professional hotel staff members assisted him through the lobby and out to whatever ride was taking him wherever it was he was going to, I dearly hope, sleep soundly, deeply, peacefully.

I’ve decided I don’t much care for expensive champagne.

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