Chapter 2: Real Regrets: Chapter 1

When the door opens, my very drunk, very irritated brother is leaning heavily against the frame. All of his weight is supported on one hand while he aggressively yanks at his navy tie with the other.

He scowls when the knot refuses to give, like it’s personally offended him by staying put. Belatedly realizing the door has opened, Crew shoves past me and stumbles into the penthouse, grumbling under his breath.

“Hello. Hi. Sure. Yeah. Come on in,” I call after his disappearing back.

I’m still in my suit from work, but it doesn’t smell like a distillery the way Crew’s does. The woodsy, buttery aroma of whiskey lingers in the entryway longer than Crew does. It’s the same scent I associate with my father. And what I usually drink.

I shut the door, sigh, and then follow my brother down the hall that leads to the living room.

When the doorbell rang, there were only two unread emails left to answer before I poured myself a stiff drink and changed into some sweatpants. I can feel that number ticking higher with each second that passes.

Kensington Consolidated does business with companies all over the world. Someone, somewhere, is always awake and replying. And when you’re struggling to make it to the top—or struggling to accept you’ll never be at the top, in my case—it means regular business hours don’t exist.

Crew is sprawled out on the brown leather couch when I walk into the living room. One arm is flung dramatically over his eyes, black fabric blocking most of his face from sight.

“Guest rooms are upstairs.”

He grunts. Doesn’t move.

I rub my forehead, feeling a literal headache form, then drop into one of the matching leather armchairs. I hired an interior decorator to furnish this place, too busy to pick out anything myself. Since I always sit on the couch and rarely have company, this is the first time I’m sitting in one of the chairs. They’re uncomfortable.

“So… What are you doing here?”

No response.

I clear my throat and cross my arms, worried I’ll be stuck in this awkward purgatory where Crew sulks—or sleeps, I can’t really tell what’s happening under his arm—and I’m stuck sitting on what feels like a wooden board waiting for him to speak or shift.

Crew visiting me at home doesn’t happen. He’s been here once—twice, maybe—since I bought this penthouse a few years ago.

We’re brothers who work together. Spending time together outside of the office or beyond the social events we’re obligated to attend as part of our prominent roles at the company our great-grandfather founded is basically unheard of. It was rare back when Crew spent his free time at Manhattan’s most elite clubs, and basically unheard of now that he has a wife, daughter, and dog.

“I got into it with Scarlett earlier.” Crew finally speaks. “Went to a bar and then came here.” He lifts his arm and fixes me with a serious, tired stare. “Don’t get married, Oliver.”

“Thanks for the unsolicited advice,” I reply, eyeing the bar cart in the corner of the room with the same longing desperation someone stranded in a storm would seek shelter.

Marriage is an unappealing prospect, low on my priority list—if it’s even on there at all. Aside from the phase in my life when I thought my wife was already chosen for me, I’ve given little thought to it. With each failed relationship, the possibility has drifted further away. If you ask any woman I dated in the past decade, I’m already married—to my job.

Ironically, Crew is the reason I have any favorable thoughts about the institution. All the marriages I’ve seen up close have fallen apart in some way, cracks cratering the surface until they collapse.

Except for Crew’s.

I’ve witnessed his relationship take hits, but I’ve never seen a fissure form. Cynical as I am, that gives me a little hope.

I glance at my brother. He’s silent. Still. I can’t even hear him breathing.

A vein in my temple pounds as I study his unmoving form. I don’t know what to say to him. Crew doesn’t want to hear about how close I was to clearing my inbox before he arrived. I have no marital wisdom to offer. But I can’t bring myself to leave him lying here, sulking and showing no signs of leaving, so I can return to my usual evening routine.

Even if that’s what he was expecting—hoping—by coming here. Crew probably showed up so he could sleep off the whiskey in silence, not for an amateur therapy session.

I focus my gaze on the windows, which boast a twenty-million-dollar view of Central Park. The lights of the city twinkle around the rectangle of greenery that’s currently just brown grass and the skeletal outlines of trees, representing a hundred places I’d rather be than hearing my little brother complain about his happy life.

Ever since he fell for the heiress our father arranged for him to marry—because in our world, billionaires marry billionaires, or at the very least multi-millionaires—Crew has changed. He starts conversations about feelings and family. He mentions our mother, Elizabeth, who he named his one-year-old daughter after. And he talks about his relationship with his wife, Scarlett, as if I have insight to offer or will make restaurant recommendations for their weekly date night.

My romantic past is boring at best and scandalous at worst. Each “relationship” has ended with tears, yelling, or my father punching me in the face.

In a word, I’m replaceable. Usually by the guy who inherited the same genes yet somehow turned out better, currently half falling off of my sofa, grumbling something about being home by eight and unreasonable expectations. Since he’s obviously not talking to me, I don’t even pretend to be paying attention.

Saying my life has ever been hard is a stretch. I’m a Kensington. Everything has always been handed to me on a platinum platter.

In theory, the easy deliverance sounds wonderful.

In reality, it means I work twice as hard for everything I accomplish, and it’s written off as nepotism or purchased achievements anyway.

That I’m always reaching for something while already having everything.

As the second son, Crew was supposed to be the spare. My supporting act. He’s always been the relaxed, charming brother. Devil may care. Rather than resent all he’s been handed already, everyone wants to pass him more.

More praise, more admiration, more attention, just more.

That’s not to say he doesn’t deserve recognition. Crew is smart and driven. People underestimated him as a cocky playboy and are lulled into a false sense of complacency now that he’s the wholesome family man.

But it stings—being constantly upstaged by your baby brother. I tried to set a good example for him. I tried to show my father I was strong enough to survive losing my mother. And all those good intentions turned into expectations I can’t seem to shake.

Crew’s reputation has changed and shifted over the years. Mine has remained constant. I’m the serious, responsible oldest child. The Kensington you can always rely upon. The dependable brother who does exactly what’s expected. The few times I’ve attempted to escape that predictability have ended horribly and have never managed to make me any happier. They’ve always turned into regrets.

So I’ve accepted my role, the same way I watched as Crew was handed the CEO position and the billionaire bride.

I didn’t want to marry Scarlett Ellsworth. I would have, but I didn’t want to.

I expected to be my father’s successor at Kensington Consolidated.

Worse, everyone else expected it.

And the depressing kicker is, I did want the coveted title. Still do, even knowing it’s forever out of my reach.

I don’t really care what people think of me. It doesn’t bother me that they whisper about why my father skipped over me. It’s my own dissatisfaction that makes it burn, not what anyone else says or thinks. They’re not the ones waking up every morning to work at a company they’ll never lead.

“How long were you planning on staying?” I ask the sprawled figure that hasn’t moved for the past few minutes.

Crew raises his arm again, this time to glare at me. “Am I inconveniencing you?”

Yes. “I figured you’d go to Asher’s.”

The arm drops. “He’s busy tonight,” Crew says.

I don’t want Crew camped out in my living room, pouting. But it stings a little, knowing I was his second choice, even if it isn’t surprising. His best friend would undoubtedly be better equipped to handle this situation.

Asher would have jokes ready or bring Crew to a club to get his mind off everything. I’ve been repeatedly told I have no sense of humor, and the last time I went clubbing was to celebrate graduating business school.

I stand and walk over to the metal bar cart, filling two glasses with the same expensive whiskey my father drinks. Even when he’s not here, he is. And it’s not just the alcohol that evokes his presence. He’s also here in the awkwardness that always hovers between Crew and me, evidence we never learned how to act naturally around each other the way most siblings do.

I set one tumbler of whiskey on the coffee table in front of Crew and then retreat to my uncomfortable armchair, downing most of the smoky alcohol in one gulp.

“What happened with Scarlett?” I ask.

Crew and Scarlett arguing is nothing new. But Crew going out to a bar and then showing up here is new. And concerning.

For all the meticulous planning about merging their empires, my father and Hanson Ellsworth never considered their children might fall in love. They thought the allure of money and power would be enough to bind Scarlett and Crew together permanently—they’re two logical, driven people who benefit more by being married than by not. And while love might have strengthened their marriage, it is also the one thing that could destroy it. My father understands that, even though I’m not sure he’s capable of the emotion himself. It’s why he didn’t stop meddling once they were married.

After attending my brother’s wedding, I would have bet five figures that he and his wife would be living in separate buildings two years later while one or both carried on discreet affairs. Last I saw them together, they looked nauseatingly happy.

Crew finally sits up and picks up the drink. He studies the amber liquid for a few seconds but doesn’t take a sip. Instead he swishes the contents around like a connoisseur, watching the whiskey slosh up the sides and then drip down the inside of the glass. “She’s pregnant,” he states, then sucks the whole drink down in one go.

“Congratulations?” It comes out as more of a question than a celebration, since Crew is frowning instead of beaming. These are better circumstances than how he told me Scarlett was pregnant the first time, but not by much.

He nods once, studying the empty tumbler like it contains all of life’s secrets. “Thanks. It wasn’t planned…again.”

“I hate to sound like a middle school health teacher, but there’s this new thing called birth control. I can grab a banana from the kitchen if you need a demonstration.”

Crew rolls his eyes and leans back with a sigh, the barest glimmer of a smile turning his lips up. “Not that it’s any of your goddamn business, but Lili had strep last month. Scarlett came down with it too.”

“Okay…” I have no idea what strep throat has to do with pregnancy.

His smile deepens a little in response to my obvious confusion. “Antibiotics mess with the pill’s effectiveness.”

“Oh.” I study Crew’s drooped posture. “Scarlett isn’t happy about the pregnancy?”

“Lili is barely one. It’s shitty timing; rouge is everywhere and Haute’s distribution tripled last year. Scarlett wants to be flying around the world and pulling all-nighters at the office and modeling her designs…and she can’t do any of that pregnant. It’s already been a struggle balancing both of our schedules with one kid. Two kids under two?” He runs a hand through his hair, then exhales deeply.

I stay silent. I have no advice to offer him on this topic either. Kids are nothing I have experience with or have really considered, aside from the abstract knowledge that as the eldest child I’d probably need to have them so they could inherit my family’s massive fortune.

Crew has taken care of that for me. Elizabeth Kensington—Lili, as she’s called now—is currently the sole heir of an unfathomable amount of money. Not only the Kensington assets but also her mother’s inheritance, which was massive to begin with and is constantly growing thanks to Scarlett’s supercharged work ethic. In addition to owning a successful magazine, Scarlett started her own fashion line shortly after she and Crew got married.

Aside from the fact it’s landed my brother on my couch, I’m happy to hear Scarlett and Crew are having another kid. It takes more of the pressure off me to settle down and do the same. Especially if this baby is a boy, since we live in a sexist society and the business world is no exception.

“I’m sure it will all work out,” I say, emphasizing how terrible I am at offering useful advice.

I can’t assure Crew of anything. I’m his older brother, yet in nearly every aspect of life, he’s far ahead of me. He’s a husband and father, weighed down by responsibilities his younger self laughed at. And they’re responsibilities he wants, not obligations.

Crew is worried about how this baby will affect Scarlett. But he’s juggling as much work at Kensington Consolidated as I am—a lot. Neither of us are great about delegating important tasks, partly to make it clear nepotism isn’t the only reason we hold prominent roles at the company. Mostly because, for all his faults, Arthur Kensington did a remarkable job of instilling a solid work ethic into both of us, despite the immense privilege and wealth we inherited. Given the size of our trust funds, neither Crew nor I needed to work a day of our lives.

“Yeah.” He holds up the empty glass. “Mind if I help myself?”

A snarky response forms at the tip of my tongue, about how he’s already helped himself to plenty that was meant to be mine. But I swallow it the same way I compartmentalize everything else. I don’t think Crew has any idea how much the CEO title matters to me, and I don’t want him to. Who gets it has never been up to him—or to me. “Go ahead,” is all I say.

Crew fills his glass and then slumps back down into the couch. His posture is defeated and exhausted. He alternates between glancing at his phone, which he set on the glass coffee table, and out the windows at the glittering city lights.

I yawn. I woke up at five a.m. to work out before heading into the office, and this is the first time I’ve sat with nothing to do all day. Exhaustion is spreading through my body, turning it sluggish and uncooperative.

If Crew was here wondering about stock options or wanting to discuss expense reports, I would know exactly how to respond. But a discussion of his marriage and a new baby has me at a loss.

He cares about his family in a way I’ve never witnessed up close. My mother died when I was seven. Long before then, I saw the cracks in my parents’ marriage. Crew grew up in the same chilly circumstances I did, and now he’s part of a family that laughs and hugs and loves and struggles openly. That doesn’t pretend to be perfect and is infinitely closer to that standard because of it.

“Isn’t the second kid supposed to be easier than the first?” I ask, taking another stab at reassurance. “I mean, you’ve done it all once before.”

Crew laughs, but there’s no humor in the sound. “Yep. Done it all once before. Went to the grocery store at two a.m. because Scarlett wanted strawberry ice cream and we had every flavor of ice cream except strawberry. Slept on a pile of dresses because she pulled everything out of her closet once her clothes stopped fitting. Once I put the toilet paper on the holder the wrong way, and she cried for twenty minutes. She will never let me forget how late I was to the hospital when she went into labor. And then there’s diapers and crying and no sleeping and having to take care of Lili on top of all that. Does that sound easier?”

“No.” Sounds terrible, honestly.

The last time I saw Lili was at Christmas, which Scarlett and Crew hosted. I attended the party at their penthouse, along with about forty other people. The highlight was that Lili had just started walking, wobbling around in a pair of toddler Mary Jane’s, and a custom velvet dress Scarlett designed. Advanced for her age, according to the whispered conversation I overheard by the champagne tower, but hardly surprising considering who her parents are. None of the chaos Crew just described was visible.

The doorbell rings before I can come up with anything else to say.

Crew doesn’t react to the sound. I stand, setting my empty glass down on the coffee table before heading down the hall to the front door.

I’m surprised—and relieved—to see my sister-in-law standing in the hallway when I open the door.

My penthouse takes up the top two floors of the building, so it’s the only door option in this hallway. But while Crew’s visits have been rare, this is the first time Scarlett has ever been here. I wasn’t even sure she knew where I lived.

“You included me on the approved list,” she states, shoving both hands into the pockets of her down jacket. Scarlett is dressed more casually than I’m used to seeing her, in black leggings and snow boots. “I thought I’d have to bribe my way up here.”

“I’ll take some rouge clothes.”

One dark eyebrow arches. “For…”

“What do you think?” The demand for Scarlett’s designs is now infamous; what her brand is most associated with. When a woman learns my last name, I’ve grown accustomed to the first question being asked is if I can get her off rouge’s waiting list.

“We’re sold out. You’ll have to manage to get laid some other way.” Scarlett smiles, but it fades fast. “Is Crew here?”

I step aside and tilt my chin toward the left. “Living room.”

“Thanks.” Rather than walk inside like I’m expecting, Scarlett reaches to the left. The next thing I know, a baby stroller and a golden retriever are filling what was once a clean, empty space.

Teddy’s tail starts wagging as soon as he sees me, recognizing me from my second, occasional job as a pet sitter. Whenever they’ve both been out of town, Scarlett and Crew have asked me to watch their dog. I like animals, but considering I basically only come home to sleep, it doesn’t seem fair to have one.

Scarlett scoops Lili out of the stroller while Teddy weaves around my legs, covering my once-pristine suit with golden hair.

“She woke up in the elevator,” Scarlett says, holding her daughter out to me. Lili’s blue eyes—identical to Crew’s—blink at me.

“Scarlett…” I’d take Crew showing up—alone—a hundred times over this. Teddy is one thing. But I’ve never babysat. I’m shocked Scarlett is even willing to entrust me with Lili.

“Five minutes.”

Reluctantly, I take the toddler. Lili squirms in my arms, then grabs my tie and yanks. For a one-year-old, she’s awfully strong.

“If she starts crying, feed her a banana,” Scarlett tells me, then heads into the living room.

“Unbelievable,” I mutter, looking down at my niece.

She pulls on my tie again.

I carry Lili into the kitchen, Teddy padding after us. He walks right over to the corner where I put his food bowl, sniffing around before curling up on the floor. Shifting Lili to one hip and hoping she can’t reach my tie from this angle, I head into the pantry, sifting through boxes of pasta and cereal for the dog treats I bought last time Teddy stayed here. Finally finding them, I grab the treats before returning to the kitchen.

The first floor of the penthouse has an open layout. I can see Scarlett sitting on the couch next to Crew. Watch as she takes his hand and says something to him. Crew turns toward Scarlett and replies with something that has her leaning into him. He pulls her close, kisses her forehead, and I feel like a voyeur in my own space, witnessing a moment not meant for anyone except the two of them.

Teddy happily munches on the treat I toss him. Lili won’t stop squirming, so I grab a banana out of the bowl and take a seat on one of the stools. I’m scared to set her down.

“Bnana.” I glance down as Lili waves a little hand around, trying to grab at the yellow fruit.

“Wow, you can talk now, huh?”

Her reply is garbled nonsense before she shoves the first bite of banana in her mouth. Within a minute, she’s eaten the entire thing.

Saving me from the dilemma of figuring out what to do next, Crew appears. He still looks tired but less stressed.

“Dada!” Lili calls as soon as she sees him.

“Hi, sweetheart.” Crew takes Lili from me, wincing as she grabs at his hair. I guess I should be grateful all she got in her grip was my tie. “You talked Uncle Oliver into a banana after bedtime?”

“I didn’t know she could talk,” I say, standing and shoving my sticky hands into my pockets.

“She has a few words in her vocabulary now,” Crew says, smiling proudly at his daughter. “She hasn’t said Mama yet though, so Scarlett pretends it’s all still gibberish.”

“I heard that.” Scarlett walks into the kitchen holding a red leash. Teddy stands and lumbers over to her, waiting patiently for her to clip it to his collar. “Thanks for watching her, Oliver.”

“Yeah, thanks for…thanks,” Crew adds. Our uncertainty about what to say to each other is mostly mutual.

I clear my throat and nod, not sure what else to say. The front door clicks shut a few seconds later, leaving silence behind. Annoyingly, I’m no longer looking forward to solitude and sweatpants the way I was before Crew showed up unexpectedly.

I look at the browning banana peel on the counter, then at the tufts of golden fur on the kitchen floor. Instead of peaceful, the penthouse feels empty.

It’s easier to be alone when it feels like a choice, instead of an inevitability.