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?”
“Oh. Yes, please.” I smile up at him.
I follow him down a hallway, and it’s like I’ve been photoshopped into one of those aspirational home decor accounts I follow on Instagram. There are creamy white walls and tall arched doorways; thick molding lining the ceilings and baseboards; wide-plank oak floors stained the perfect shade of chestnut; large-scale artwork that’s the quintessential mix of modern and masculine. Every step screams luxury. It even smells expensive, like one of those overpriced home stores in Soho where I love to browse but can’t afford to actually buy anything.
There are a couple of guest rooms in addition to the primary bedroom, a space I skitter past with only the briefest of peeks. It’s like my brain instinctively knows that any more than a cursory glance might spark the fuse of my already oversexed imagination. From just one quick glimpse, I’m able to gather that Jack has a giant bed （for acrobatic, Cirque du Soleil–style sexual activity?）， crisp white hotel linens （for comfortably sleeping in the nude?）， and a classic mid-century modern chest of drawers （for housing boxers or briefs?）。 Must. Redirect. Thoughts.
His office is the only room that isn’t immaculately styled. His desk is strewn with papers, crumpled receipts, and piles of mail; file folders lay askew in messy stacks. An old coffee mug sits forgotten alongside a large computer monitor, a dozen sticky notes stuck to its frame. He must really only work and sleep.
I start absently flipping through a leadership book that’s out on his desk before noticing he’s using our US Open ticket stub as a bookmark. When I hold it up with raised eyebrows, he just smiles, unembarrassed.
Like an alien called home to its mothership, I’m immediately drawn to the built-in bookshelves covering one wall that stretch all the way to the ceiling, spines stuffed into every nook and cranny. There’s even a Beauty and the Beast–style rolling library ladder. I want to hang off it like Belle and belt, “Bonjour!”
We continue the tour, though I glance behind me longingly as he leads me back out to the hallway. I’d love to steal back in there and rummage through his files, but it’s not like I can just slip away without him noticing. My mind shuffles through plausible cover stories: Pretend I need to make a phone call? Challenge him to a game of hide-and-seek? Feign diarrhea?
We end up in a high-ceilinged great room with floor-to-ceiling picture windows offering stunning panoramic views of the city. In the center of the room is a conversation area set up in an inviting vignette: a pair of club chairs upholstered in a subtle, soft plaid flanking a long butterscotch-leather couch I’d bet costs more than I make in a year. An interior designer has definitely been here, because I don’t know any straight men who’d have coffee table books stacked on their sideboard with an organically shaped wooden bowl perched on top.
It’s beautiful. Meticulously so, really, but the thought that comes to mind is model home—technically flawless, but devoid of any unique character or distinguishing details about its inhabitant. If I’d thought I was going to glean all these new insights into Jack’s psyche by handling his knickknacks or poring over his personal photos, I was sorely mistaken.