The breakfast room is bright; sunlight streams in through the palladian windows. The air smells of bacon and coffee and the subtle saltiness of sea air drifting in from off the Sound. A platter of croissants and slices of lightly toasted Portuguese bread sit on the center of the table, flanked by delicate Royal Delft dishes holding softened butter, marmalade, and beach plum jam. Will saunters in, his hair tousled and his shirt rumpled, testament to the late hour he stumbled home the night before. Despite the gorgeous day unfolding and the leisurely breakfast awaiting them, there’s tension humming in the room.
His mother is mid-sentence, and as he picks up a plate and loads it with soft scrambled eggs and buttery crisped potatoes, he begins to gather what’s going on.
His aunt Caroline—his mother’s sister, younger by three years—has just informed them that she isn’t coming this weekend as planned.
“Of course she RSVP’ed yes,” his mother said tightly, in response to his father’s blandly placid question. “She’s hosting the party with me.”
His mother is referring to the baby shower that they’re throwing at the house on Saturday afternoon for their cousin Keaton’s daughter Mackie, who’s having her first baby in eight weeks. The party has been in the works for months; Caroline being an aggressively bossy partner who was constantly calling in the evenings to weigh in on details like cucumber versus radish tea sandwiches or whether they should invite Keaton’s neighbors from Wellesley even though they’d never attend.
Caroline was originally slated to stay in the guesthouse with her husband and two daughters, but last week Will’s mother had shifted the arrangements because Keaton’s husband tore his Achilles tendon playing squash at the Yale Club and was barely able to walk, let alone traipse back and forth to a hotel. Upon hearing that she was relegated to the Harbor View Hotel (to be clear, this was the nicest hotel on the island and Will’s mother had booked the entire Captain’s Cottage for them, a plum property right in the center of town), she had suddenly remembered that one of her daughters (Alexandra, the seven-year-old) had a tennis lesson that weekend.
“A tennis lesson?” Jack said incredulously. “She’s bailing on the party you’ve been planning for months because she’s being snippy about the accommodations, and she’s blaming it on a tennis lesson? That’s not even a very creative excuse.”
“Alright then,” Will’s father said, reaching across the table for the salt shaker. “I think that’s enough discussion about that. Alexandra is a crack tennis player at such a young age, really it’s impressive.”
Will looked at him, eyes wide and serious. “That’s absolutely not okay!” Will nearly shouted, causing his father to drop the piece of marmalade-laden toast he was holding.
“William!” his mother reprimanded him crisply. “What in the world?”
“I’m not going to sit here, as always, and listen to this bullshit. No one here thinks that is okay behavior. You could just, like, talk about it for a change. Nothing catastrophic would happen if we decided to acknowledge something messy, for once.”
Half of the table was appalled, but the other half was inwardly thrilled, his sister-in-law Allison in particular. Ali had grown up in Breckenridge with parents who talked easily and openly about everything from their own marriage to politics, and the world of tightly repressed emotions remains bewildering to her. Privately, she thought Will was both brave and out of his mind to take on Hayward Rutherford but in her eleven years with Jack she had learned enough to stay quiet.
Hayward cleared his throat loudly, and stood up, shaking his napkin out and placing it next to his glass of orange juice (freshly squeezed). “I’m going to call Stuart and check to see if he’s in for the ten o’clock tee time. Otherwise, Jack, there’s a space for you.”
He strode out of the room and Will watched his retreating figure, then turned back to the table. “Seriously? Mom. Seriously?”
She looked at him, her jaw set firmly. “He, like me, doesn’t necessarily want to start the morning with histrionics. Would anyone like more coffee?”
She pushed her chair back and followed Hayward’s path towards the kitchen, leaving Will and Ali and Jack to sit in silence until she was gone.
Will looked at both of them, raising his eyebrows.
“Unbelievable.”
Ali burst out laughing. “No, it’s entirely believable. I mean, you have to laugh!”
“Do you?” Will said back, although his mouth was quirking up into a smile. “Let’s just say I gave it the old college try.”
“Dude, don’t encourage Ali. This is basically her dream come true to finally put the screws to Dad.”
“Hey,” she said gently. “I consider myself a creature of admirable restraint, can we agree on that?”
Jack picked up his coffee mug, and raised it to her in a mock toast. “You are a wonder woman Ali. But no, I don’t award you extra points for not antagonizing my father over breakfast. Will, you get points docked, because now he’ll be in a mood all morning and I’ll probably bear the brunt of it for nine holes straight.”
“Uhh, just don’t play. Noah’s picking me up in half an hour to sail to Cuttyhunk. Come with.”
Jack glances at Ali. “For the day? You’re coming back tonight?”
“Probably not. Noah’s bringing Sadie and we’re going to stay for the raw bar, then probably just sleep on the boat.”
Sailing over for the Cuttyhunk floating raw bar is a rite of passage both Jack and Will had undergone when they were teenagers—an adventure so steeped in summertime tradition that it’s taken on the magic of a ritual. Around sunset, when pinks and neons begin to streak the blue sky, a Boston Whaler with the words RAW BAR emblazoned on the side putters out into the harbor, making the rounds from mooring to mooring, offering up freshly shucked oysters with a bottle of mignonette sauce and stuffed quahogs, the toasted sausage-and-breadcrumb filling still steaming hot from the oven.
Anyone who knows the ropes knows to bring your own beer (Will already has a cooler packed with two six-packs of Provincetown Brewing’s session IPA and another sour ale from Vermont, because Noah is a true beer snob and he’s pretty sure he won’t have tried this one yet), and to pack cocktail accouterments: sweatshirts and blankets for after the sun goes down, weed (if you’re Will), a deck of cards, and more food (Will would have just thrown a bag of chips into the boat, but as soon as his mother heard the word Cuttyhunk, she began assembling her go-to platter—smoked bluefish paté, melba toast, and and there’s nothing he could do to stop her).
“Well then he can’t go,” Ali interjects. “We have Madeline’s engagement party tonight, remember?”
Jack groans audibly. “All the more reason to evacuate the island!”
Ali smacks him lightly on the shoulder. “She’s your friend. I’m the one who should be dreading it.”
“Friend is a stretch,” Will teases. “She is still in love with Jack, you know that right? The entire engagement is probably staged in the hopes that he’ll throw a glass of Champagne in Connor’s face and profess his undying love for Madeline right in front of the lobster roll station.”
Jack grimaces, “Can you guys drop it please?” Ali is cracking up now, because this is an endless joke on Jack’s behalf and he despises it, likely because there is more than a grain of truth to it all.
Madeline Case, soon to be Madeline Sutcliffe when she marries Connor Sutcliffe III in September, had been Jack’s girlfriend the summers after junior and senior year of high school. It was a quintessential June to August romance: they rode bikes into town and kissed on the Flying Horses carousel and skinny-dipped at sunset in the waters off the Aquinnah Cliffs and got drunk off vodka lemonades at beach bonfires. Each fall, they’d go their separate ways: she back to Ardmore and he back to Newton. Jack would spend the school year thinking about…everything a teenage boy thought about, but certainly not about Madeline, and Madeline would spend them pining for him, writing long perfume-scented letters and counting down the days until Memorial Day.
When it came time for college, she went to Trinity and he left for Stanford, eliciting an extremely tearful goodbye on Madeline’s part and an attempt to extract a promise to stay together. Jack was entirely out of his element in this kind of emotional terrain, so he loosely steered clear of committing one way or another, and spent the first semester of freshman year dodging Madeline’s calls. He told her it was too far to come home for fall break, instead flying to Bellingham to kayak the San Juan Islands with his roommates. Over Christmas break, he took the most cowardly approach to breaking up by kissing another girl (Bailey Griffith, one of Madeline’s best friends, to add salt to the wound) in front of her at a party and ever since, Madeline has pretended to affect some degree of public scorn, which anyone can see is barely disguised unrequited adoration.
Decades later, she still treats him with a certain nervous energy. Ali, along with most of his friends, loves to tease him about Madeline which he goes along with laughingly, but in truth he wishes he never had to see Madeline at all. Partly it’s some long-standing guilt over treating her poorly (Madeline is, at her core, a nice and relatively harmless person) and partly it’s the feeling it gives him that he’s never really moved on from high school.
The years passed, the faces got older, the houses nicer, the clothes more expensive, but nothing fundamentally changed., only now they talked about stocks instead of soccer games or mortgages instead of who was doing MDMA at the Disco Biscuits concert the weekend before, and at any given party, Jimmy Nichols will get too drunk and be the loudest in the room and Julie Linden and Catherine Walton will hold court making snide remarks about other women.
For Jack, the saving grace is Ali. Meeting Ali was his own private rebellion against everything that tied him to home. Ali was a breath of fresh air (literally, in some senses, as she’s the most outdoorsy person he’s ever met). She’s funny and smart and curious about the world. She teases but she doesn’t gossip, at least not in the competitive sport sort of way he’s used to from the girls he grew up with.
Ali is the most easy-going woman he’s ever dated, by far. She would happily have stayed in Colorado after they met. He could see their life there: hiking Boreas Pass with their dogs on Sundays, listening to live music outside over beers at Broken Compass Brewing, skipping work to go ski Peak 9 on winter mornings. And he almost did, but Ali knew him better than he knew himself, and she recognized that Jack had New England in his veins. Try as he might to embrace his wanderlust and denigrate the closed social circles of the East Coast, he would never feel like he was home anywhere else. After two years in Colorado, they bought a five-bedroom brick townhouse in Beacon Hill and that was that.
Ali is the head of media relations for Deloitte, a job that requires an extreme amount of authority, calm competence, and intelligence, all of which she possesses in spades. Combined with her blond good looks and cheerful demeanor, it’s easy to see why Jack fell for her almost immediately when they met.
He was at a bachelor party in Napa, a few glasses of Pinot Noir deep into a tasting at Domaine Carneros; she was entertaining clients. Ali had been wearing navy trousers and a crisp white button-down, her freckled cheeks flush with a summertime tan, her blond hair pulled back into a low bun, gold jewelry winking at her neck. Jack, along with every other person with a pulse in her immediate radius, was smitten.
Ali swears she only noticed Jack with a modicum of annoyance over how much noise his group was making in the tasting room, acting like they were sophomores at a dive bar instead of men in their thirties at one of the most beautiful wineries in California. That night, he’d run into her at La Toque: He’d snuck glances at her over seven courses of the chef’s tasting menu, finally getting up the nerve to walk over and introduce himself after the fig brulée with brown butter ice cream. Uncharacteristically, she’d agreed to meet him for coffee the next morning—later she’ll say the only reason she said yes was to get him to leave the table where she was trying to smooth over a sticky conversation with a senior correspondent from CNN.
Over cappuccinos and griddled English muffins at Model Bakery, she discovered she actually liked Jack: his self-effacing humor, his unbridled enthusiasm that matched hers, his willingness to go anywhere and do anything. She had a work trip to Boston the following week; he convinced her to have dinner with him—spicy shrimp tacos and pisco sours at Puro Ceviche; the rest is history.
To her surprise, Ali fell in love with Boston. She loves the seasons, the cobblestone charm of Acorn Street, the lights at nighttime games at Fenway, the musty smell of the travel section at Brattle Book Shop. The closeness of the sea and the smell of the coast that hangs in the air. She likes quiet fall evenings eating coq au vin at Ma Maison then walking home in the crisp cold; the linguine alle vongole at Ristorante Limoncello; the signature martini at The Newbury Hotel; the spicy ham and pineapple pizza at Florina.
As much as she embraced her new city, a tiny part of her felt hemmed in by the skyline. She was used to the brimming blue backdrop of Colorado mountains and forest as far as the eye could see. In the winter, when she isn’t traveling for work, they spend weeks back in Colorado. Her sister Annalise had an extremely luxe ski chalet in Aspen; the four of them (Jack, Ali, Anna, and Anna’s husband Hugh) would ski all day and lounge in the hot plunge pool on the deck at night, drinking ridiculously expensive wine.
Hugh was an adorably nice guy who’d invented an app in his mid-twenties that connected college kids with people willing to do their laundry—”the Uber of clean clothes,” he liked to joke—which had been bought for many millions of dollars. Then, he’d nearly tripled that money by lucking out and investing almost all of it in a company that brewed non-alcoholic beer before anyone else was, and had rocketed to success. Hugh now had more money than he knew what to do with, but as someone with intellectual curiosity and a need to be busy, he’d started a company that mentored small start-ups through the investing process. He focused on the wellness space: companies that made gym shorts out of endangered alpaca wool and non-toxic bamboo alarm clocks that whispered meditative mantras before bed and that sort of thing.
Hugh and Anna had two children: Eliot, who was six, and Peter, who was eight. Ali felt the distance between her nephews keenly, like an invisible thread pulled taut against her heart. Peter was quiet and cerebral; he liked to play trains and draw elaborate diagrams of planes and airports for Ali, his rosebud lips pressed tightly into a firm line in concentration. He had gorgeously thick blond curls and eyes that were an arrestingly deep shade of blue. Eliot, on the other hand, had inherited Hugh’s dark good looks: a flop of nearly black hair, hazel eyes, and an impish dimple in both cheeks.
Now that the boys are old enough to happily stay with their grandparents for a week (Ali’s parents dote on their grandchildren, taking them hiking and fly-fishing in the Rockies and plying them with homemade French toast and introducing them to the wonders of black-and-white Cary Grant films), Hugh and Anna travel more and more, often with Jack and Ali. They start a tradition of spending the first week in February somewhere warm, rotating who gets to pick the destination each year. It became a bit of one-upmanship: Hugh has chosen Buenos Aires and Tenerife and Jack picked Cabo and Kauai, largely for the surfing and the golf. They all agreed that Anna’s choices—Grenada and Cartagena—were some of the best trips. In Cartagena they stayed at Hotel Casa San Augustin, the lime-washed stucco walls and trailing bougainvillea even dreamier than they’d imagined. They stayed in a suite with a sprawling private terrace paved with terracotta tiles and a plunge pool bordered by high walls painted with 17th-century frescoes over which palm trees dipped. They sunbathed topless on the beaches at Bocagrande and washed down plates of fried cassava spiked with hogao sauce with spiced rum cocktails.
Ali’s trips were the most memorable of all, one for the sheer disaster of it all and the other for the sheer luck.
Her first choice had been to Costa Rica. The plan was to stay in the Monteverde Cloud Forest for six days of hiking and zip-lining. Ali had booked two suites at the Cielo Lodge, an eco-resort so chic they felt odd wandering in each day in their sweaty, mud-splattered hiking gear. On paper, the trip should have been perfect, except that in the world’s strangest twist of fate, Jack got kidney stones on the third day and while they were in the (extremely small, extremely dimly lit) hospital waiting for him, Anna got up from the slumped vinyl waiting room chairs to refill her paper cup of military-strength coffee, slipped on a wet floor, and broke her left ankle. They ended up spending the final three days drinking guaro sours on their balcony and ordering room service while Anna relaxed in the hammock—all in all, one of their more entertaining stories to retell at cocktail parties.
For her second round, which was eight years ago, Ali had taken them to Montego Bay. From the moment they touched down on the tarmac, the trip had seemed golden, like everything clicked into place in some cosmic way. Upon arrival at Round Hill, the receptionist had explained that a pipe had burst above the two adjoining suites they’d booked. He apologized profusely, looking anxious (the hotel was renowned for top-quality hospitality). Jack had nodded tersely and asked, “So, we have nowhere to stay?”
The receptionist had smiled widely, “No! Of course not. Happily we have one room available, at no additional charge of course, but it is a bit far from the main lobby.” The room in question turned out to be the 8,000 square foot Estate Villa, perched high above the resort, reachable only by golf cart. It had two pools, a dedicated staff, in-villa breakfast each morning, and an unparalleled view of the water.
It kept getting better from there. Tiny bits of luck kept cropping up. On Monday, a pod of dolphins circled them while snorkeling. The next afternoon they went cliff diving into the warm, gently bobbing waves in front of Rick’s Cafe in Negril. After climbing out and drying off, they threw on clothes and walked barefoot into the cafe for a round of rum punches. A few guys were on the small stage, tuning their guitars, and when they began to play, Hugh turned to the rest of them and almost scream-whispered, “Holy shit! That’s Dave Grohl!”
It turned out that the Foo Fighters frontman regularly rented a house down on the beach, and some of the band members were there for the week. The bartender leaned over as he placed their drinks in front of them and explained that sometimes the band would spontaneously play a set or two for any lucky patrons who happened to be there. Hugh was so excited he was practically pink, as giddy as a teenage girl meeting a pop star: Foo Fighters had been his favorite band since he was old enough to tape a poster up on the back of his door.
The trip unspooled beautifully. Jack and Hugh golfed while Ali and Anna paddleboarded and windsurfed—they all fell into bed at night, sunburned and happily exhausted. The afternoons were lazy: chaise lounges on the beach; reading; swimming; bowls of freshly cut fruit on ice. After showers, the cold water stinging their skin, tight from hours in the sun, they’d climb into a tiny open-air cab and drive off for an adventure: rafting down the Rio Grande or hiking the narrow trails up into the jungle.
And then, of course, they’d met Ben.
Their taxi driver, an astoundingly chatty man with a mouthful of gold teeth and an infectious grin, had sworn up and down that no trip to Jamaica was complete with a late dinner dinner of goat curry and sauteed callaloo at Sips & Bites in downtown Negril. Next door, reggae music floated out of the doors of a crooked-looking wooden bar painted bright pink and turquoise.
People were spilling out onto the porch; lights were strung up into the palm trees, illuminating the ocean and waves beyond. All four of them looked at each other and wordlessly walked into the bar. They had just ordered a third round of daiquiris; Ali and Hugh were tipsy and dancing, sweaty and happy, on the crowded dance floor. Jack stood up and grabbed Ali’s hand, motioning to everyone to walk over to the restaurant to eat (it had been over seven hours since they’d had lunch—jerk chicken and roasted sweet potatoes and cold Red Stripes—and the cocktails, combined with the sun and the lack of food, were making him feel dizzy and light-headed).
The restaurant, if you could call it that, was nothing more than a brightly lit shack with an open kitchen and a window where you could stand and call your order up to the cheerful woman manning the register. Her accent was thick and lilting; she asked a series of quick, rapid-fire questions to each customer, then sang the orders back to the chefs behind her, laughing and sweating over the grill. “Extra spicy? Ackee on side?”
Hugh and Jack carried the plates of food over to a plastic table and pulled up chairs. Next to them, a man sat alone, tucking into a plate of stewed oxtail over rice and peas. He could have been a twin of Daniel Craig in the James Bond era: tanned and fit with blond hair streaked with silver. In a low-pitched British accent, he leaned over and asked Hugh if he could borrow a bottle of hot sauce from their table.
“Mine’s a bit stuck, it seems,” he gestured to the bottle on his own table. Hugh asked where he was staying, and they began to strike up a conversation. The other three kept eating, noticing that Hugh and the British man’s conversation had grown more focused, no longer the loose small talk of two strangers on vacation.
Anna tapped Hugh on the shoulder. “We’re walking over to that little ice cream place we saw across the street. Coming?”
“I’ll stay here. Ben and I are hashing out a few things.”
Anna gave him a quizzical look. “Sure. We’ll bring you back a cone,” she smiled politely at the other man and walked off.
Twenty minutes later they returned, licking cones of creamy coconut ginger ice cream, heavily infused with rum. Hugh was alone.
“Where’d your friend go?” Ali asked teasingly.
Between licks of his ice cream cone, Hugh explained that Ben was Benjamin Henderson, one of the most influential angel investors in Great Britain. It turned out that they’d both gone to the same international high school program (United World College in Wales; Hugh’s parents were aging hippies who believed wholeheartedly in uniquely experiential education). Ben was a few years older than Hugh, but attending UWC was like gaining membership in a very exclusive, very small club that lasted you for your entire life. Meeting someone else who’d matriculated guaranteed an automatic kinship.
It turned out that Ben Henderson had just invested in a C-rate Italian soccer team, the sort of promising yet ragtag misfits about whom a great indie film would probably have been made. In the haze of all the daiquiris and the heat of the evening, Ben had convinced Hugh to invest also, and he had.
Six years later, the team had—thanks to several coaching changes and the recruitment of three wildly talented local teenagers—transformed itself into a rising success, earning entry to the FIFA World Cup. Ben and Hugh were now part-owners of one of the world’s top soccer teams, which garnered them both a not inconsequential income but more importantly, endless bragging rights.
Whenever it came time for someone to pick the next trip, they all referenced Jamaica. “Try to top the Foo Fighters. Seriously, just try.”
Coconut Ginger Ice Cream
Makes 1 quart
400ml full-fat canned coconut milk
1/2 cup whole milk
2 tablespoons minced fresh ginger
4 egg yolks
1/3 cup sugar
1/2 cup heavy cream
2 tablespoons rum
Combine the coconut milk, whole milk, and minced ginger in a saucepan and bring to a simmer over medium heat. Once it simmers, remove it from the heat and let sit until it cools slightly.
In a large heatproof bowl, whisk together the egg yolks and sugar until pale yellow.
Add 1/2 of the coconut milk mixture to the eggs, whisking constantly, and whisk until well-combined.
Place the bowl with the egg mixture over a double boiler and slowly add the remaining coconut milk mixture, whisking constantly.
Cook until the custard thickens and coats the back of a spoon, stirring often.
Once the custard thickens, remove from the heat and let cool in the refrigerator (or in an ice bath) until chilled.
Once chilled, strain the mixture over a sieve to get rid of the ginger, then whisk in the cream and rum.
Pour into an ice cream maker and process according to the instructions. Once churned, freeze.