The Rom Con

“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.

I swallow this setback as I step closer to the window to take in the incredible multimillion-dollar view of Central Park, which looks like a lush carpet of green treetops from this height. “Wow,” I murmur. So this is how the other half lives.

I can feel him come up behind me, my skin prickling with awareness. “Right? It’s the reason I chose the place. Hard to feel sorry for yourself with this view.”

I swivel my head one hundred and eighty degrees just so I can give him some side-eye. “And what possible reason might you have to feel sorry for yourself?”

He raises and lowers a shoulder. “You’d be surprised.”

I tuck that vague answer into my back pocket for the time being, then continue to turn in a slow circle like I’m surveying the room . . . but what I’m actually doing is casing the joint, mwa-ha-ha. I have no idea what I’m expecting to find—a file folder left unattended on his coffee table conveniently labeled Brawler Top-Secret Blackmail Material?—but it’s intimidatingly clean in here. Spotless, actually, like he’s stashed a live-in housekeeper under that ginormous couch of his. Argh. What’s the point of infiltrating enemy territory if I’m forced to retreat empty-handed?

My brain sparks with an idea, and I saunter over to the sideboard, skimming my fingertips over his coffee table books. “So are you always this neat? Or did you stuff all your skeletons in the closet before I came over?”

He gives me an Aw, shucks expression. “I’m afraid you’ve uncovered my dark secret: I’m actually quite boring. I don’t have anything to hide.” Ha! I’ll be the judge of that, mister.

I cast him an impish look and reach for one of the cabinet knobs menacingly. “So if I opened up this cabinet right here, I wouldn’t find anything incriminating? No Spice Girls or Barry Manilow CDs? No notebooks full of angsty teenage poetry? No collection of Beanie Babies or blow-up dolls? No creepy taxidermy?”

“Nah, I keep that stuff at the office.”

I snort a laugh.

“But now I’m kinda wishing I had something in there that would shock you.” His eyes dance with amusement as he nods his head. “But let’s live dangerously—go ahead and see what’s behind door number one.”

I keep my eyes trained on him, slow-playing it for dramatic effect, before throwing the door open with a flourish. “Board games?” I clap a hand over my mouth to stifle my laughter.

It’s a lot of board games, too. Neat stacks of everything from Sorry! to Scattergories to Boggle to Operation fill the cabinet to bursting. I feel like I’ve stepped back in time to the childhood playroom in my parents’ house. I crouch down to get a closer look and laugh when I see there’s even a Trivial Pursuit: F?R?I?E?N?D?S edition.

“Oh, my . . .” I pull out Rummikub as a steady stream of memories washes over me. “This one takes me back. We used to play this for hours at my grandparents’ house when they’d babysit us.” I replace it on the top of the stack and shudder at Perfection, a game that always terrified me. It’s a panic attack in a box. “Why do you have all these? Do you host a lot of game nights?”

“Not exactly.” He presses his lips together like he’s trying to decide how much to divulge. “I’m a bit of a board game enthusiast.” He says it seriously, like it’s an academic pursuit akin to pursuing a PhD.

“A board game enthusiast? Oh, wow. Geez, okay. I only just realized.”

“Realized what?”

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