AS PREDICTED, JACK immediately accepted my offer to cook him Engagement Chicken (which I innocuously framed as “dinner”), and if he thought this was a peculiar activity for a third date, he didn’t let on. Honestly, he sounded so relieved that I finally called him back that he probably would’ve said yes to BASE jumping. He even had me send over the list of ingredients so his assistant could stock his kitchen in preparation. I wanted to ask if his assistant could recommend a dry cleaner that specializes in vintage clothing, but figured that might raise a red flag.
Jack lives in a brand-new, luxury high-rise condo building overlooking Central Park, which, I’ll admit, is a wee bit intimidating. Most of my colleagues are like me: barely scraping by, living paycheck to paycheck while eking out a living doing the noble but financially unrewarding job of journalism. Although I’ve dated men with income levels all over the spectrum (and grew up comfortably middle-class myself), Jack’s wealth is in a different echelon altogether. And I don’t know, there’s just something about the “old family money” crowd that’s always made me uncomfortable, with their Nantucket summer homes and needlepoint belts and upper-crusty, seemingly impenetrable Ivy League caste system. It all seems designed to make you feel less than, like even if I became super-successful in my own right, I’d never really be accepted into their exclusive club.
But I force myself to set those feelings aside as I enter his building, politely greeting the uniformed doorman holding open the wide double doors. The lobby is just as grand as the posh exterior: soaring ceilings, a tastefully appointed sitting area with high-backed chairs and plushly upholstered couches flanking a sleek double-sided fireplace, an imposing gold-and-crystal chandelier that casts a perfectly flattering shade of light on the room. My heels click across the marble floors as I make my way toward the older gentleman manning the concierge desk. He’s got thick eyebrows and hair that’s more salt than pepper, and I watch his eyes brighten as I approach.
He smiles warmly at me, a gold nameplate reading CLIFF winking at me from his chest. “Miss Sutton?”
Now that’s what I call service. “Now how could you possibly know my name, Cliff?”
He laughs at my dumb joke, and I fall in love with him instantly. “Mr. Bradford let me know a beautiful woman would be arriving, though I’m afraid he didn’t do you justice.” He comes out from behind the desk and offers me an arm. “Right this way.”
He leads me to an elevator bank, and once he keys in a special code for Jack’s apartment—he’s got the entire floor, gulp—and I’m zooming upward, I attempt to shake off my nerves by recapping my goals for the night:
Get him talking and see what he’ll let slip.
Don’t fall under his spell no matter how good he smells or how twinkly his eyes.
Less Betty, more Cassidy. He seems to open up more when I’m myself.
The pressure’s on because this is it—my last-ditch attempt to find something incriminating. If I can’t get anywhere tonight, I’m out of ideas and out of time. I need to pin him down and peel away his layers—and prevent him from Houdini-ing his way out of sharing anything personal.
I think of Gran’s latest tips—and not the silly ones like Kiss him even if he’s sweaty or Offer to rub his shoulders—but her real ones, the good-faith relationship advice she gave me that’s worth its weight in gold: Make him feel special. Be your best self for him. Support and encourage him. Dressing up for him isn’t inauthentic or putting on airs; it’s showing him he matters. Considering your partner before yourself isn’t subservience, but an act of love.
I take a deep breath and smooth my dress, fingering the frilly secret weapon that’s tucked discreetly into my purse. I’m ready for a night of playing house.
Jack’s waiting for me as soon as the elevator doors slide open, his face lit with the anticipation of a kid standing at the threshold of a candy store.
“Hey, you.” He envelops me in a hug before I can even step out, and I get a lungful of his cologne, a clean, forest-fresh scent that makes me think of alpine lakes and sturdy redwoods, like he regularly bathes in naturally occurring springs or majestic waterfalls. I wish I could place it exactly, but the only scent I can reliably identify is Acqua di Gio (those high school memories run deep). One thing I can say for sure, though: It is definitely not Force by Eric Jessup.
“I’m happy to see you,” he says when he pulls back, eyes shining with pleasure. He has serious golden retriever energy tonight. “And looking beautiful, as always.”
While this evening’s strategy may be more about letting the real Cassidy shine through, I’m still dressed like Betty, this time in a sleeveless pink linen shift with an embroidered neckline that Nat swears is an exact replica of one Jackie O once wore. And while there’s plenty to complain about between the corsets and cone bras, I’ve come to appreciate just how chic and timeless that era of fashion actually was—so much so, in fact, that I’ve decided to embrace my mid-century makeover for the duration of this experiment. I refuse to admit it to Nat, but the infusion of color into my wardrobe has actually added some pep to my step. And no, I absolutely did not use some of the tips from those TikTok tutorials to give my auburn hair some soft Rita Hayworth–inspired pin curls. That would be taking things too far.
I know, I know, I have sartorial Stockholm syndrome. But as they say, “When in Rome”—or, er, Roman Holiday.
In a nod toward “more Cassidy, less Betty,” I did, however, ditch the dainty handbags in favor of my trusty overstuffed mom tote. While I highly doubt Jack (or any guy) would notice such a subtle change, I worried it might cause whiplash if my character shift was too jarring, if I suddenly went from Elizabeth Taylor to Taylor Swift overnight.
Of course, Jack’s experiencing no such style dysmorphia. Tonight, he’s dressed casually in a pair of broken-in jeans and a charcoal gray T-shirt that’s stretched tight around his biceps—so tight, in fact, that the seams appear to be clinging on for dear life. Either his muscles are larger than the average male’s (I chance a glance at them—yep), or whoever designed this T-shirt did women everywhere a solid by botching the sleeve-to-torso fabric ratio. I silently salute said couturier for their service.
I suddenly realize this is the first time I’ve seen him out of a suit, and it should come as no surprise that he wears the laid-back look just as well. I take a moment to sight-see, admiring the ruggedly handsome view. He’s still rocking some serious Big Man on Campus on his home turf energy, but there’s a looseness to him tonight, a quieter, more relaxed confidence that’s new—and frankly, refreshing. I immediately sense that this stripped-down model is the real Jack, that the besuited power broker I’ve grown accustomed to must be his own costume, a suit of armor disguising his true self from the world.
“So what do you think?”
“Hmm?” I tear my eyes from where they’ve settled on the smooth, corded muscle of his bicep. I think I’ve been wetting my lips without realizing it. “I’m sorry, what was that?”
If he noticed me drooling, he gives no sign. “Would you like a tour?”