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  For my husband, John—my love, my favorite,

  and my happily ever after.

  This book would not exist without you.

  Who’s Who in Anna K

  (in order of appearance)

  LOLLY S.

  Seventeen, junior at the Spence School. Girlfriend of Steven K., older sister of Kimmie.

  STEVEN K.

  Eighteen, senior at Collegiate School. Older brother of Anna, boyfriend of Lolly.

  DUSTIN L.

  Eighteen, senior at Stuyvesant High School. Homework tutor to Steven, younger brother of Nicholas.

  KIMMIE S.

  Fifteen, sophomore at Spence. Younger sister of Lolly.

  ALEXIA VRONSKY (ALSO KNOWN AS VRONSKY OR COUNT VRONSKY)

  Sixteen, sophomore at Collegiate. Cousin of Beatrice.

  ANNA K.

  Seventeen, junior at Greenwich Academy. Younger sister of Steven, girlfriend of Alexander.

  ALEXANDER W. (ALSO KNOWN AS THE GREENWICH OG)

  Nineteen, freshman at Harvard University. Boyfriend of Anna K., older half-brother of Eleanor.

  ELEANOR W.

  Fifteen, sophomore at Greenwich Academy. Younger half-sister of Alexander.

  BEATRICE D. (ALSO KNOWN AS BEA)

  Seventeen, junior at Greenwich Academy. Cousin of Alexia.

  NICHOLAS L.

  Twenty-one. Older brother of Dustin, boyfriend of Natalia.

  MURF G.

  Sixteen, sophomore at Greenwich High School. Childhood friend of Vronsky, stable hand at Staugas Farms.

  NATALIA T.

  Eighteen, lives in Arizona. Girlfriend of Nicholas.

  Part One

  I

  Every happy teenage girl is the same,

  while every unhappy teenage girl is miserable in her own special way.

  The whole thing was a fucking disaster. Lolly found out her boyfriend Steven was cheating on her while she was getting his Apple Watch outfitted with a new wristband at the Hermès store on Madison Avenue. Steven didn’t even know she had his Apple Watch. Twenty minutes ago, he decided to do back-to-back SoulCycle classes, while Lolly begged off staying for the second class with him. (Her new gluten-free diet lacked the necessary carbs for her to handle doing a double sesh without passing out.)

  She was telling him the truth while also needing the time and access to his Apple Watch to take it to the store for a new wristband, his present for their eighteen-month “screw-a-versary,” which happened to be the very next day. (Lolly didn’t love commemorating their first official date with this crude moniker, but Steven called it that. Lolly went along because she loved him.) So while Steven was climbing an imaginary hill to the steady beat of Dua Lipa’s “IDGAF” at the East 83rd Street studio, Lolly was fifteen blocks south standing at the counter of Hermès.

  She was deciding between the traditional double-wrap band in iconic orange leather and the more hetero choice in matte black. She was admiring the orange band on her own delicate wrist, when Steven’s Apple Watch vibrated and a tiny tit pic flashed on the screen, followed by the gray text bubble containing the letters: DTF? *eggplant emoji*

  Lolly tapped the touch-screen to see the photo again. Confirming the worst, she froze until her fight-or-flight impulse kicked in. Lolly chose flight, forgetting to take off the new band as she ran out, and was stopped by the burly security guard who blocked the door. Lolly, never good at holding back tears, started to sob pitifully, staring down at her beloved Gucci sneakers (the ones with the glittering snakes) that Steven had bought for her this past Christmas. Unsure of what to do, the security guard placed his arms around the crying girl. She pressed her face into his poly-blend jacket and whispered, “It’s a mistake. It must be a mistake. Please let it be a goddamn mistake.”

  Eventually the beautiful Japanese saleswoman decked out in head-to-toe Hermès, who had been helping Lolly before, took charge of the situation and brought her into the back room. She sat her down on a small couch and gave her a Perrier, which gave Lolly hiccups and made her start crying even harder. The whole scene was quite embarrassing for all parties involved. Kimiko, who had worked at Hermès for ten years, was no stranger to the rampant cheating of the city’s wealthiest citizens, many of whom were her clients, but there was something about witnessing this seventeen-year-old girl’s loss of innocence IRL that unexpectedly moved her.

  Once they had gotten rid of her hiccups, Lolly asked if she should scroll through the rest of her boyfriend’s messages or not. Kimiko said in a quiet voice, “Better to find out how bad it is now when you’re not alone.” Soon both women were mesmerized by the appallingly graphic nature of Lolly’s boyfriend’s relationship with the mysterious “Brad.” Steven had used a fake name in his contacts, but there was no chance “Brad” was a guy judging from the plethora of female body parts being photographed and sent to Steven over the last several weeks. There was even one blurry up-the-skirt video that made both women wince and groan in unison.

  Lolly purchased an Hermès Iris belt buckle and reversible strap in bleu saphir and bleu Brighton to thank Kimiko for her kindness and left the store fifteen minutes later, Uber-ing straight to Steven’s parents’ massive four-bedroom penthouse apartment at 15 Central Park West (his parents were currently in Aspen skiing) to wait for his cheating ass. She tipped Gustavo the doorman a Benjamin not to tell Steven she was upstairs, citing a surprise gift and waving the orange Hermès shopping bag as proof. The doorman took her money, but clearly warned Steven anyway because ten minutes later her bf showed up carrying red deli roses in his still sweaty hands.

  He had managed only the words “Lolly baby, what’s wrong?” before his mother’s favorite Lalique Tourbillons amber vase whizzed past him and smashed into the marble foyer floor. He stared at his normally demure girlfriend in shock when she said, “Just tell me one thing Steven…!” her voice now building in ferocity, “When’s your screw-a-versary with Brad?!” She was now holding up his Apple Watch as digital proof. Steven stared at it and knew he was irrefutably busted.

  Steven’s momentary confusion quickly turned to sheepish shame and he activated full grovel mode. He tried to approach her, but she backed away from him. “Don’t come near me, you … you … disgusting pig! That’s right, I saw all the vile thirst trap pics that slut Brad sent you!” she screamed. At the mention of the pictures, the latest naked pic that Steven had seen on his phone after class popped into his brain and the tiniest lascivious smile flickered across his face. He was an eighteen-year-old boy, after all.

  Unfortunately, Lolly caught Steven’s smirk.

  The noise she emitted was more animal than human and she ran past him, almost knocking him over in the process. Having nowhere to run except the end of the hall, Lolly opened the door to the master bedroom and slammed the heavy door behind her. She locked the door and ran straight into Steven’s mother’s walk-in closet. She threw herself facedown on the bloodred crushed-velvet chaise at its center and began to cry harder than she had ever
cried before.

  Steven tried talking to Lolly through the door, but he was met only with the occasional sound of things being thrown at the door. An hour later he was in the living room watching SportsCenter highlights and eating his third pepperoni Hot Pockets when he received the following text from his buddy Kaedon: Dude, did U buy ur gf a fur coat?!!! Steven paused the TV and quickly discovered he was already unfriended and blocked across all Lolly’s social media accounts. (So much for their 453-day Snap streak!) He texted Kaedon back: screenshot?

  Seconds later he received a selfie of a possibly naked Lolly wearing one of his mother’s fur coats. Lolly, being much tinier than his mother, looked ridiculous in the chevron-quilted Russian sable, her eyes wild and ringed with mascara. She looked like a rabid raccoon … one who just found out that her boyfriend was cheating on her and was royally pissed. He shook his head and knew the situation was now far beyond his skills to rectify. Steven fired off a string of texts to his sister Anna in Greenwich, Connecticut, telling her he was in dire need of her immediate in-person assistance. His sister was younger than he was, but much wiser, especially when it came to relationships and all the tricky emotions that came with them.

  Ten minutes later he received a text from Anna announcing her arrival into Grand Central at 8:55 P.M. Before he could text back telling her to take a car, two more texts arrived explaining the latest snowfall was backing up traffic, with Google Maps showing how a train would be the fastest way into Manhattan for her. Anna’s last text stated she expected him to pick her up at Grand Central in person so she could hear his side of the 911 gf emergency!! Steven replied with only the single character k, as there was no emoji to depict the grand scale of how fucked he truly was.

  II

  After playing Shadow of War to clear his head and sipping some of his dad’s Glenmorangie Pride 1974 scotch to calm his nerves, Steven tried once again to talk to Lolly through the door. A moment later he finally received some indication of his girlfriend’s state of mind, but it wasn’t good. Lolly pushed the black-and-white photo strip of the two of them, which they had made together in the photo-booth at her little sister Kimmie’s bat mitzvah a year and a half ago, underneath the door. This picture was at one time (like four hours ago!) Lolly’s most cherished possession, which she carried around in her LV wallet.

  Steven often found his girlfriend staring at the photo strip, but it had been in a different condition than the one he was looking at presently. His eyes had been poked out in each of the four pictures and she had also drawn tiny dicks on his forehead.

  “Lolly, baby, it didn’t mean anything. It’s you I love. I swear.” Saying this out loud he knew it was true. When Steven was fourteen years old, his father discovered him getting a BJ from Jenna H. while her parents were over for dinner. His father sent the humiliated girl out of the room and sat Steven down and told him two things. First, he needed to get better at hiding if he didn’t want to get caught. And second, the more important lesson, Steven needed to learn the difference between loving sex with girls and loving the girl he was having sex with.

  At a loss for what to say and knowing Lolly adored Anna, as every girl adored his younger sister as soon as they met her, Steven announced Anna was on her way into the city, hoping Lolly would take this as a sign he wasn’t giving up easily. But again, he was met with only silence. He did however get a text from the doorman alerting him to the fact that Dustin L. was on his way up. Steven sighed, pissed at himself for forgetting to cancel his thrice-weekly homework tutoring session. He stood up in the hallway and headed toward the front door.

  He considered talking to Dustin about his current dilemma, as Dustin was one of the smartest guys he knew, but Steven decided there was no way Dustin would take his side. Dustin was technically one of Steven’s oldest friends, as their mothers had happened to attend the same mommy-and-me music classes, so they played together as babies every Tuesday and Thursday and were “best buds” until the age of five. But then Dustin’s parents divorced, and he went to public school while Steven went to private, which meant they hadn’t run in the same social circles for years and had only recently gotten back in touch when Dustin became Steven’s homework tutor.

  Currently Dustin was a senior graduating with honors from Stuyvesant in June, while Steven was a second-time senior at Collegiate. Steven had attended Collegiate for elementary school but was kicked out in fifth grade when he got busted pantsing a classmate during PE. Next, he was kicked out of Xavier in seventh grade for pot, then Riverdale in ninth grade for fighting. He then attended Horace Mann for a few semesters and was now back at Collegiate on a very short leash.

  Steven had his mother to thank for his reinstatement. She’d had to call in a few favors to make it happen. And since one of the conditions of his academic probation was maintaining a high GPA, his mother had hired a string of overpriced homework tutors that all quit after a week or two, citing Steven’s poor attitude (i.e., filthy mouth) and even worse work ethic. At her wit’s end, his mother finally had the brilliant idea to call Dustin’s mother to see if Dustin, whose impressive academic accomplishments were always touted on fb, would agree to work with Steven as his new homework tutor. His mother knew that while her son had little respect for the authority of adults, he coveted the approval of his peers.

  Dustin had been adamantly opposed to tutoring Steven when his mother brought it up to him last October. He pointed out that he and Steven were only “friends” because of the happenstance of their two mothers meeting, and by all accounts, the two boys could not have had more different childhoods. “We have nothing in common!” Dustin moaned. “What will we talk about?”

  “What you’re being paid to talk about … homework,” was her calm reply.

  Dustin let out a deep sigh and rolled his eyes. Where Steven was a good-looking, rich party boy from Manhattan’s highest social circle, Dustin was none of those things. Dustin was adopted and knew nothing about his biological parents. Well, he did know that his teenage mother had left a note saying he should be given to Tamar L., “the nice social worker lady who was smart and kind, when she was just a kid from a fucked-up home living with her messed-up mom.” She wanted a better life for her own kid, which is why she knew she should give him up.

  And so, one Friday night on her way to temple for her first Shabbat service in quite some time, Tamar received a call from a social worker at a hospital and was given one hour to decide if she wanted to become the mother of a two-day-old newborn. Taking it as a test of her lapsed piety, she leaned forward and gave her cab driver the address to St. Luke’s on 112th Street. When she told her husband about her intentions and explained her taxicab epiphany, Dustin’s soon-to-be adoptive father didn’t give it a moment’s hesitation (even though they already had a three-year-old) before saying, “I’m in!” And Tamar was consumed with a feeling of security that she had married the right man. Eighteen years later, Dustin’s mom still told this story, but with the caveat that while she was right about adopting Dustin, she had spoken too soon about her now ex-husband.

  Dustin had grown up to be a quiet, serious boy whose adoptive parents continually made jokes to their friends that their own genes could have never produced such a smart kid, and Dustin, knowing the routine, would respond that he was pretty sure his biological parents could never have raised him to be such a good Jewish boy. (Only recently with the rise of Drake’s popularity was Dustin’s blackness combined with his Jewish upbringing thought of by his peers as “cool” rather than “weird.”) What people didn’t know was that Dustin was also prone to panic attacks and had been in therapy for his anxiety since the age of ten, which was why the thought of tutoring a “crazy rich kid” like Steven tied his stomach in knots. “No way. I can’t do it, Mom,” Dustin said. “Steven’s the epitome of the one percent, and me helping him is like going over to the dark side. I’m no Kylo Ren.”

  Dustin’s mother, being a very practical woman, calmly explained to her son that he was making far too much of a b
ig deal over the matter. “You’re being too emotional, Dusty,” she said. “This is not Star Wars. This is real life, and it’s not fair of you to write Steven off just because he was born into great wealth. No one’s saying you have to be best friends with him. This is a job where you’re providing a needed service and getting paid well for doing it. You’ll make more money in the next eight months than I make in an entire year.” The going rate for homework tutors in Manhattan was easily two hundred bucks an hour, and Steven’s mom was of course offering more, which meant Dustin would be clearing over two thousand dollars a week along with a bonus of ten grand if Steven ended the year with a GPA above a 3.2.

  “Don’t you see how insane that is?” Dustin replied. “You’re a licensed professional who spends her days helping the underprivileged, people who actually need help. You’re the one who’s always saying social workers and public-school teachers are the two noblest professions that are grossly undervalued in today’s world. How can you in good conscience suggest I do this?”

  “Stop being so melodramatic! You’re going to college next year and this will spare you working at some crappy part-time job for spending money. That’s the way I’m looking at it, and so should you.” Dustin found his mother’s viewpoint to be simplistic and shortsighted but when he tried to tell her as much, she refused to debate the matter with him further and instead insisted he talk the matter over with someone else before turning it down.

  Dustin decided to end the matter quickly by going to the highest authority first, the rabbi at their temple. Much to Dustin’s surprise, Rabbi Kennison agreed with his mother, citing the example that she herself had worked at McDonald’s in high school. “I asked every customer if they wanted to supersize their meal; does that mean I’m responsible for the obesity problem in America?” she asked. Before Dustin could answer, she added that Dustin would be performing a mitzvah by using his God-given intellectual gifts to help another. “What if Steven grows up and becomes a senator because you helped him with his studies?”