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The Miseducation of Henry Cane

A stunning coming-of-age novel about one young man's eye-opening sexual awakening at the hands of an intriguing older woman.

Henry Cane knows exactly what he’s going to do with the rest of his life.

That’s the problem.

Born into the rarefied world of Manhattan wealth and privilege, after graduating from Princeton, Henry is about to start his perfectly planned out life. He's always known he will move back to Manhattan and be groomed to take over his father’s publishing business. He's destined to date a string of appropriate girls until he dates the most appropriate girl and asks her to marry him.

It’s all so awfully tedious.

But Henry's been given eight weeks to do something else, to be an entirely different person. When his parents leave him alone in their Sag Harbor estate for the summer, Henry embarks on a double life as Joe, a blue collar fisherman on the other side of the bay. Once ensconced in his fake identity, he finds himself entangled in an affair with an alluring, older European woman—who happens to be married. As he becomes more and more infatuated with her, their affair threatens to unravel his tightly wound story, and could jeopardize his entire future.

This is the story of a boy becoming a man, shaped by the hands of women who truly control the narrative.

The Miseducation of Henry Cane CHAPTER ONE
Two months earlier . . . June 1, 1994

“Will you miss me?”

Caroline had asked me this twice already, and each time I gave her the required “Yes, of course . . . very much.”

I wondered if she’d ask a fourth time, and I told myself that if she did I’d come up with something more clever. In fact, I started practicing witty things I could say in my mind, but they all sounded cheesy and lame, so we rode the rest of the way in silence.

Before she got out of the car at the British Airways doors at JFK I gave her an awkward hug, because, for all intents and purposes, we’d broken up the night before in a very courteous and official way. She’d be spending the summer in London interning with the Royal Shakespeare Company and hoped to stay on in the fall as an associate producer. We’d gone back and forth for months about the idea of staying together. I needed her to be the one to break it off. I’d always been terrible at making big decisions. If I’m being honest I was used to women making all my decisions for me: first my mom, then Caroline. I’m not gonna lie about the fact that I liked it. I functioned best when things just sort of happened to me. When Caroline finally announced we were definitely calling it quits, in an act that involved plenty of tears and bold proclamations about what we both really deserved and needed, she told me she still wanted me to be the one to see her off at the airport. I’d never once told her no during the course of our three-year relationship, and I saw no reason to start.

I carried her luggage to the curbside check-in and tipped the guy there twenty bucks for no real reason except I wanted Caroline’s last image of me to be me handing off her bags and tipping some guy too much. She leaned in and kissed me goodbye on the side of my mouth the way you’d accidentally kiss an elderly aunt.

Caroline Alby. I’d loved her the moment I set eyes on her, but by the time I was back on the Long Island Expressway I felt a strange relief, the kind of feeling that comes when winter becomes spring and you get to take off a too-heavy and too-itchy sweater. I would have stayed with Caroline as long as she wanted me to. I hadn’t known the freedom would feel both sweet and terrifying.

My mother kept threatening to sell our beach house. Every single June that I can remember, Deidre Cane packed two suitcases for each of us and drove the three hours from our town house on East Eighty-Third Street to the beach house in Sag Harbor. Once she was there she flung open all the windows, wiped her finger through the collected winter dust, and declared, “We should get rid of this old wreck and get an apartment in Paris.”

For a long time I believed that was actually what she wanted. Only in my teen years did I understand it was sarcasm or maybe irony. It took a while before I became fairly certain my mother just enjoyed being unhappy.

The house, a weather-beaten colonial revival, had certainly seen better days, but it wasn’t a wreck by any means. This was the Hamptons after all. The peeling paint and the floors that forever smelled a little like salt, sand, and damp towels only made me love it more. I knew my mother secretly took pride in our rickety old house with its musty furniture. Old-money houses out east tended to have an up-market thrift-store decorative style, whereas new-money houses were all white leather and sharp edges. I once attended a party with my parents at the home of this Internet millionaire. That’s what everyone was calling him, “that Internet millionaire,” like it was a strange sort of profession, an encyclopedia salesman or that guy who sells you potions out of a briefcase. “That Internet millionaire” helped build Prodigy or had a diaper delivery service you ordered through AOL or something like that.

“It looks like it was decorated by a Colombian drug lord,” one of my mother’s friends said to another woman. “And not even one of the interesting ones.”

But this summer, Deidre had gotten her Parisian wish, or at least a taste of it. My father had been invited to teach a summer session at the Sorbonne, something about publishing the great American novel, and Mother said if he didn’t take it she was finally going to leave him for Stan the butcher, a man she insisted knew how to take a damn vacation. How she knew anything intimate about Stan, a man who also had a lazy eye and was missing a canine tooth, was beyond me, but Mother did have the ability to talk to anyone about anything, and maybe she’d managed to unlock secrets about Stan beyond how he trimmed a pork shank.

My father suggested renting out our old house at the beach, but my mother wouldn’t hear of it.

“Strangers putting their filthy feet on my furniture,” she scoffed.

“I thought you couldn’t stand that wreck of a place anyway,” my father replied with a bemused smile.

“It’s my wreck, and I don’t want anyone else in it. Henry will spend the summer there before he starts work with you in the fall. Let him relax a little before you and the cutthroat world of publishing break his spirit.”

I couldn’t object. Having the beach house all to myself for the entire summer was a better plan than staying in our place in the city, which, by the way, was also the complete opposite of a wreck—a four-floor town house with actual servants’ quarters. There hadn’t been any servants in the house since at least the turn of the last century, but the quarters were still there all the same. Mother used them for storing holiday ornaments and one time for an au pair from Germany who Deidre said smelled like sauerkraut.

Their house wouldn’t be my house for that much longer. Beginning in September I had a lease on a studio on West Eighth Street. I would never say out loud that I wanted to escape the Upper East Side. I just wanted something new, something different. And maybe a part of me liked the fact that my mother didn’t love trekking below Fourteenth Street unless she was picking up whitefish from Russ & Daughters.

Relaxation was a foreign concept to my father, but because my mother was keen on it he accepted it and Paris all the same. I’m fairly certain I inherited my desperate need to please beautiful women from him.

It took only two hours to get to the beach from the airport. That’s what happens when you leave on a Wednesday afternoon. I rolled all the windows down and indulged in the guilty pleasure of singing at the top of my lungs to the entire CD of Madonna’s greatest hits, which Caroline had left in the six-disc changer. I hadn’t exactly forgotten to remind her about it.

Nothing had changed about the beach house since I’d seen it last September, and its sameness comforted me. By the time I opened all the windows and swiped away enough of the dust from the furniture, I had no idea what I wanted to do next. Endless days of nothing stretched ahead of me. I had a stack of novels I’d been meaning to read, and part of me relished the idea of staying put in the house for an entire week as I made my way through them in delicious silence.

I didn’t get that luxury

“Hey, dildo.”

Sperry never knocked. He hadn’t knocked since he started wandering into our beach house when he was five years old. It’s how we became friends—he just wandered on into a stranger’s house. His parents bought the place next door, and they were the kind of parents who had no trouble setting their child loose on the neighborhood while they unpacked. He came right into our kitchen, opened our fridge, and made himself a ham sandwich. My mother found him sitting at our kitchen table and sent him up to my room to play. That was how Deidre parented in the late seventies. Sperry was a real big kid. My mother called him husky and was always trying to get him to eat things like celery sticks with peanut butter and raisins, and instead he’d demand a sloppy joe.

It turned out he lived not too far from us in the city, and we both wound up at Collegiate for kindergarten through the twelfth grade. When I left for college in New Jersey, Sperry went to Dartmouth and made a big deal about how it was just his safety school, even though everyone knew his dad paid for a new wing at the main library to get him in. If I thought hard about it (and I tried not to), Sperry and I shouldn’t still be friends. He’d grown into the kind of frat boy who would go down in Dartmouth history for rushing the field naked during the Ivy championships and doing a five-minute keg stand, whereas I could never even find the keg at most college parties. But it was easier to keep him around than to get rid of him. He was familiar and comfortable, like waffles or a crocheted quilt.

Sperry opened my freezer and turned back to look at me with disappointment in his puppy-like eyes.

“No ice cream.”

“Haven’t shopped yet.”

How had it just occurred to me that I would need to go to the market and fill the refrigerator myself? The realization was both enlightening and embarrassing.

“I gotta eat, man.”

“You know there’s probably food at your house.”

“There definitely isn’t. Kelli-Anne is on a new diet where she doesn’t eat things that have mass.”

Kelli-Anne was Sperry’s latest stepmom. She wasn’t all that much older than us. In fact, we could have overlapped in high school. Sperry was saved that indignity. Kelli-Anne came from some small town in Texas.

Sperry mimicked Kelli-Anne’s high-pitched, nasally twang. “Brett, you could stand to quit eatin’ so much too. You’re as fat as a sow ready for slaughter.” He placed one hand on either side of his formidable gut and shook it like he was a mall Santa Claus. Nobody but Sperry’s parents called him by his given name, Brett. We called him Sperry since he owned more boat shoes than anyone I’d ever met. No one had ever seen anything else on his feet. Not even when he was just a chubby kid raiding my mother’s fridge.

“Come on. Let’s get out of this house. Let’s get crabs,” Sperry insisted.

“You had them. Remember junior year.” That was a joke that didn’t get old.

“You’re funny. At least I got laid in high school. Nothing a little antibiotic didn’t clear up. Let’s go.” He was already halfway out the door. “We’ll take the boat and get some good claws across the bay.”

By the boat he meant my boat, which should have irritated me, but I let it go.

“You want to go all the way over to Greenport?” I complained.

“They taste better out there. So do the beers. And the girls are prettier.”

“The girls out there just don’t know you. That makes them prettier,” I countered. “You haven’t done anything to offend them yet.”

“Touché. Come on, dildo. I’m starving.”

My boat wasn’t anything special. But it was all mine, every single piece of her. I started building her from scratch when I was thirteen years old. My grandfather was alive back then, and the only thing he wanted to do besides work was show me how to build a wooden boat, a childhood dream of his. Her name was Arabella, from the Captain Blood pirate stories, which I read when I was way too young to be reading them because they were filled with blood and guts and nasty men doing nasty things. My Arabella was a flat-bottomed skiff made entirely out of sweet chestnut, and, in my opinion, she was only getting better with age. I didn’t let just anyone go out on the boat. I’d never once taken a girl out on her; it would feel curiously unfaithful.

The water was smooth as glass, and the tides were in our favor to whip us around Shelter Island and over to the North Fork in less than an hour.

Sperry removed his salmon-pink polo shirt and let his pasty chest bake in the midafternoon sun, stretching his arms skyward. That was another difference between the two of us. I preferred to keep my shirt on unless I was planning on swimming, showering, or getting with a girl. At the age of twenty-one I was the rare man who still slept in a pair of pajamas bought by my mother. Sperry liked to be naked as often as possible.

“This summer is gonna rule,” he shouted, even though I was well within earshot. Like me, Sperry was taking a break for the summer before he’d start a job his dad got for him in the mergers and acquisitions department of Goldman. Unlike me, Sperry was wildly excited about his life come September. Sperry had never wanted to do anything but work in M&A at Goldman. It’s what his dad had been doing for the past thirty years and what his grandfather did for fifty years before that.

I knew I should feel grateful that I had such a good job lined up for me. I’m not one of those people who take these kinds of things for granted. Still, I was less enthusiastic about my future working for my father than Sperry was. I also wasn’t even that excited for the next two months. I knew this summer would be exactly like every summer we had at the beach. That’s the thing about the Hamptons. It’s all about the same people doing the same things in the same places and then pretending something new and interesting was happening.

Sperry kept going on and on about his plans for our epic season. His specialty was making plans. In another life, another world, he should have been an event or wedding planner, maybe a hotel concierge, not a corporate banker.

“Johnson’s cousin is bouncing at the Sand Trap and he promised to let us cut the line as long as we bring some hot chicks. I feel like Beth is pretty hot, and she’s got enough decent-looking friends to get us in all summer.” Beth was Sperry’s stepsister from his dad’s third marriage, the shortest marriage of the five, and the two of them never actually lived under the same roof, which is probably why it was so easy for Sperry to constantly fantasize about taking off her clothes.

“It’s still creepy when you talk about how hot Beth is,” I said.

Sperry flipped his palms toward the blazing sun.

“I can’t help it. The heart wants what the heart wants.” He pounded on his chest like he was Tarzan and did a cannonball off the boat and into the water, making a splash that forced me to hold tight to the steering wheel.

Because it was a Wednesday we found a spot to dock right next to this place called the Feisty Crab and Sperry was out of the boat before I could even tie her up. By the time I got to the table he’d ordered a basket of fries, clam strips, crab legs, and two frosty mugs of beer. The Feisty Crab was small and warm, with taxidermy fish and photos of fishermen covering the wooden walls. The crowd, even on a weekday, was feistier than the crab, which, to be honest, was perfectly serviceable, but not any better than a crab we could have ordered in Sag Harbor or Montauk. It was absolutely better than anything we could get in East Hampton, where all the food was the same as country-club food the world over: overcooked chicken, frozen crab legs, and enormous rubbery shrimp covered in ketchup that someone claimed was cocktail sauce.

The Feisty Crab’s menu consisted of things that came directly out of the ocean and other things that had been dropped in a deep fryer for approximately seven minutes.

“I’m in love with the waitress,” Sperry informed me as we dug into our food.

“Which one?”

“That sloe-eyed goddess who just wiped the crab crumbs off the table.” He pointed with his chubby index finger.

“She’s pretty,” I said, because Sperry likes validation and because it was true.

“Man. Are you still hung up on Caroline? She’s definitely boning a Frenchman at thirty thousand feet as we speak.”

I didn’t tell him I’d imagined the same thing as I pulled away from JFK. I took a long sip of my beer instead.

“Nah. I’m just getting reacclimated to being a single man.” That was true. Caroline was only the second woman I’d ever slept with, a fact Sperry may have thought but not known for sure. Contrary to his previous jest, I did have sex in high school, I just didn’t talk about it the way Sperry did all the time. I’d done it seven times to be exact, with the same girl—Annie Westover. And then I met Caroline the first day of freshman orientation. We weren’t exactly strangers. We had circled each other for years in various Manhattan and Hamptons social circles, but that icebreaker session in Annenberg Hall was the first time we’d ever spoken to each other beyond Hey and Are you spending the summer out east? It turned out we were in the same microeconomics section, a requirement that neither of us had any interest in. We sat next to each other there because we’d already developed a vague familiarity. I became her study buddy for all of freshman year. I figured spending time in her dorm room was better than staying in my own double and listening to my roommate have loud sex with Michiko, our Japanese RA. Caroline dated this guy named Carter for the entire first semester. Carter happened to be the Princeton quarterback and the lead baritone in the campus’s most adored a cappella group. It probably doesn’t mean much anywhere else, but at an Ivy League college the Venn intersection of football player with a cappella geek is equivalent to a Mount Olympus–level god. But Carter broke her heart when he fell for the second-string baritone. I pretended to be incredibly surprised, let her cry on my shoulder, and delivered pints of rocky road to her dorm room every night for a week. My persistent presence eventually wore her down, and sometime during sophomore year she started calling me her boyfriend, and that was that. I think she knew I would never break her heart.

Sperry pulled a paper wrapper halfway off a straw and then blew it into my face. “Earth to dildo! You can ask the waitress out if you want to. I’m a very good friend. I’m chivalrous. Like a knight.” He raised his arm as if he were pulling out an imaginary sword and managed to knock all the condiments off the table. Sperry’s first beer was already gone, and he was twirling his index finger in the air to summon another.

I picked up the wrapper and threw it back in his general direction, letting it settle in the dregs of his beer glass. “All yours. I’m not big on long-distance. But this is a logistically tricky romance for you. How will you get across the bay without a boat? You gonna drive all the way around Riverhead?”

“You’ll bring me, man. This is all we have to do for the entire summer.”

The thought of doing this every day with Sperry felt worse than the existential sameness of the rest of my life come September.

I took this class called Philosophy of the Twentieth-Century Man my junior year at Princeton. Being in the privileged position of knowing exactly what you’re going to do with the rest of your life means you can take classes as frivolous and enjoyable as Philosophy of the Twentieth-Century Man. God, I loved that class. We spent nearly half the semester on Viktor Frankl and man’s search for meaning. Of course we did. Frankl was pretty much the crux of man thinking about philosophy in the last hundred years. Caroline took the class too, and she hated it. Really hated it. “Why is it Twentieth-Century Man and not Woman?” she scoffed. I didn’t have a good answer. She stopped going about three weeks in, a couple of days after it was too late to officially quit the class without getting an incomplete, which meant I took even more diligent notes to please her. I couldn’t get enough of man’s search for meaning. It was one of the few classes that really got stuck in my brain.

“Everything can be taken from a man but one thing: the last of the human freedoms—to choose one’s attitude in any given set of circumstances, to choose one’s own way.”

Sitting at the Feisty Crab with Sperry I let Frankl’s line pass through my mind a few times.

I wasn’t paying attention to Sperry’s slurry come-on to the waitress. “I seem to have lost my phone number. Can I have yours?” Her snorty laugh brought me back to reality.

That one usually worked with about 50 percent accuracy. I’d once said it aloud myself, just to hear how it sounded coming out of my mouth. I never said it again. Guys like me shouldn’t say things like that.

“You seem like a guy who loses a lot of things.” She reached into her pocket, pulled out a blank piece of paper, and wrote her name, Kelli, with a little heart over the i, and her number on it.

She got real chatty then. She was eighteen and would be starting classes at Hofstra in the fall. She grew up just a few streets over from here and wanted to study fashion design.

“You know Isaac Mizrahi is a family friend,” Sperry bragged. “I could probably introduce you.”

The famous fashion designer was actually a friend of Sperry’s father’s and not Sperry’s. The only time I’d ever seen them interact was last summer at the Watermill Center benefit when Sperry passed out in the back seat of Mr. Mizrahi’s car, thinking it was his own car. Mr. Mizrahi was not pleased, and I knew that he would not consider Sperry a friend at all.

Sperry then made a big show to Kelli of pointing across the water to indicate where we lived, on the right side of the bay. His pudgy digit became a laser pointer on a chart indicating relative wealth and success.

“When do you get off? Get on our boat.” Now it was our boat. “And we’ll all go out in Sag.”

I shot him a severe glance. It was one thing to drive the boat back tipsy with just Sperry and me on it. Somehow that didn’t worry me. I’d been keeping the two of us safe since Sperry learned how to huff on whipped cream cans in the eighth grade. But I hated having strangers on the boat. He knew it too. He avoided my eyes, knowing exactly what I was thinking.

“I’m hitting the bathroom,” I said, and pushed my chair back a little too forcefully. It made a noise like fingernails scraping against a chalkboard, and that shut Sperry up for a second.

“You want another beer?”

“Sure. Whatever. But then we’ve got to get back.”

Sperry rolled his eyes. “Because you’ve got so much to do, man.”

The Feisty Crab had only a single bathroom, and there was a line of mostly women waiting to use it. I supposed the men probably went outside and peed behind their cars in the parking lot or off the docks. I didn’t actually consider doing it myself. I wish I could. But I was always terrified I would be caught by a well-appointed woman like my mother with my zipper down. That woman, dressed like Deidre, in her silk camisole, pink clamdiggers, and pearls would see me and my very average penis and scream or call for the police. Nope, I couldn’t pee outside. Instead, I occupied myself by reading notes and ads pinned to the large community bulletin board next to the bathroom. An orange cat named Oscar had been missing for almost a month. A woman named Shana would clean your house for $9 an hour. The auxiliary club was hosting a bake sale for some guy named Rooster who needed help raising money for his chemotherapy treatments. An evening of poetry at the Last Drop Coffee Shop would be held on Thursday night.

An older woman, maybe in her forties, with chemically bleached blond hair came out of the bathroom. She wore a crop top revealing a tight tummy and a tattoo of a dolphin leaping over her navel.

“Toilet won’t flush,” she announced in a singsong voice to imply that the broken toilet was absolutely not her fault and everyone in line groaned. The next person waiting plugged her nose and went in anyway.

“Why don’t you just pee off the pier?” a girl who couldn’t be more than fifteen asked me.

“You know that’s illegal.”

“Pussy,” she murmured under her breath.

I was about to abandon the line and just try to get Sperry back on the boat when a yellow-lined piece of paper caught my eye. It was pinned all the way in the top-left corner of the bulletin board, handwritten, and the ink was fading. A tearaway phone number was written five times vertically on the bottom.

FISHERMAN WANTED—No experience neccesary.

I first noticed that necessary was misspelled, and I had an intense desire to find a pen and correct the mistake. Then Frankl manifested again—though I actually heard it in Caroline’s deep and husky voice this time, the one she’d used in my dorm room when she repeated it back to me from my own notes.

“?‘To choose one’s attitude in any given set of circumstances, to choose one’s own way.’ What does that even mean?” she’d asked. And then, “Why should I care what this guy thinks?”

Why should you care? The man survived the Holocaust. That’s what I should have said. But then she peeled off her top, and she wasn’t wearing a bra beneath her itchy Fair Isle sweater, so I didn’t say anything.

The bathroom line was shorter now. Some had given up, dropped out, and I was the next person waiting. When the door opened I looked at the yellow paper one last time.

“You going?” the girl behind me barked. “?’Cause I’m gonna go if you’re not going.”

“I’m going,” I said. But first I ripped away one of the phone numbers.

Maybe, for at least a couple of months, I could choose my own way.

Charles Brooks is an editor and publisher. He lives in New York City with his two daughters. The Miseducation of Henry Cane is his first novel.