The Rom Con

Jack and I see each other almost every day, sometimes for a quick lunch, more often for a lingering dinner, and I look forward to each meal like a kid counts down to recess. Our weekends are spent doing a random hodgepodge of things—brunch in Hudson Yards, an outdoor concert in Central Park, taking in a Giants game—and despite the warnings about his demanding workload, he seems to have no problem making time for me.

While his relationship with his mom may be thorny, she clearly did something right—there’s an old-school, gallant quality to Jack’s courtship style that could only be the result of a mother’s touch. He leads me through doorways with a hand to my back; helps me into my coat; walks beside or behind me, never in front; shields me from rain; refuses to let me carry (or pay for) anything. He’s affectionate and attentive, as generous with his time as he is with his money. While it’s a bit of an adjustment dating someone with an income so disparate to mine—no restaurant is too nice and no tickets too expensive, which is about as far outside of my penny-pinching, budget-controlled lifestyle as it gets—Jack is so unassuming about it all that any self-consciousness I may have felt quickly melts away.

While I may not have his resources, I do my best to spoil him with the one thing I can give him in return: my attention. Eager to make up for my past hot-and-cold behavior, I create a revised romantic punch list and start checking things off one by one. I hide sweet (and sometimes spicy) notes around his apartment for him to find later. I snag him gifts from the steady stream of press samples that pour into the Siren offices, like an advance copy of a memoir written by an entrepreneur I know he admires. I compliment him openly and often, and ogle him shamelessly. I curate an oldies-themed Spotify playlist of our greatest hits and surprise him with it. I start monitoring sports headlines so I can converse with him semi-intelligently about his workday. I swallow my pride and give the Engagement Chicken another shot, and this time, I nail it. I even bake him a batch of my specialty break-and-bake cookies for dessert (what, you thought I’d make ’em from scratch? I haven’t changed that much).

But watching his reaction to these small acts of kindness is my favorite part. An adorable carousel of emotions plays out on his face every time: surprise (widened eyes; raised eyebrows), pleasure (a boyish grin; flushed cheeks), followed by affection (his hands on my hips dragging me closer; lingering full-body hugs; leisurely, bone-melting kisses). He’s clearly not used to people doing things for him, which could break my heart if I think about it too long. Even more surprising? How gratifying these acts of service are for me.

I’m the happiest I’ve ever been.

With every one of his playful texts and dimpled smiles and goodnight kisses, I feel the world shifting beneath my feet. It’s not lost on me that the man I once dismissed as undateable is now responsible for the healthiest relationship I’ve ever been in. Gran’s guidance is resonating more deeply than I ever could have imagined: Let him know you’re thinking of him. Make him feel cherished. Never stop trying to win his heart.

It’s a Sunday afternoon, and Jack and I have just finished hitting up a street fair, a fall-themed affair bursting with hay bales and spiked cider and wild children hopped up on kettle corn and face paint fumes. It’s hard to believe it’s already October, but the changing leaves and brisk air nipping at my forearms don’t lie. Now would be the time to borrow Jack’s coat, but like an idiot I actually had the foresight to bring my own. Somewhere, Gran is trolling me for the missed opportunity.

We’re strolling through the Upper West Side now, and I’m introducing Jack to one of my favorite (free) activities: stoop-spotting (which is basically just an excuse for me to drool over the brownstones I love so much). I point to the one in front of us, its steps piled high with colorful pumpkins and squashes and funky-looking gourds of indeterminate origin. Matching cornstalks flank either side of the dramatic arched doorway while galvanized steel buckets brimming with mums crowd the threshold. It’s a picturesque autumn vignette straight out of Hocus Pocus. “This one’s definitely my favorite.”

Jack snorts. “You said that about the last one.”

“I really mean it this time, though.”

“You said that too.”

I blow out a puff of air, mock-wounded. “I think you’re missing the point of the game, sir. They’re all my favorite.”

He hooks his index finger into my belt loop and tugs me back against his chest, wrapping his arms around me from behind and enveloping me in one of his signature full-body hugs. I flash to something Nat said a couple of days ago: If you turn into one of those sickening couples who walk around with their hands in each other’s back pockets, I’ll have to kill you.

I relax against him and grip his forearms, staring up at the house wistfully. “If I could live anywhere in the city, I’d pick one of these brownstones.”

“Oh yeah? Why’s that?” His breath is a curl of warm smoke against my ear. It’s pumpkin spice and everything nice.

“Have you ever been inside one? They’re so dreamy, so quintessentially New York. They have so much character—creaky floors, two-hundred-year-old millwork. The banisters alone! I just love everything about them.”

“They’re probably all haunted.”

“Meh, living with ghosts is a small price to pay. My dream is to curl up in a window seat in comfy socks, reading or writing, listening to the rain pelt the window. Can’t you just picture it in a winter storm? Like you’re inside a snow globe.” I sigh in contentment at the thought of it.

He hums and flexes his arms, squeezing me tighter. I’m steeped in his scent, cloaked in his embrace. Mummified in Jack. “Where am I in this fantasy?”

“You’re making me dinner. Or rubbing my feet. Either is acceptable.”

He laughs, and I nod decisively.

“That’s it, we’re definitely coming back to this house in December. You know they’ll go all out for Christmas. Lights, wreaths, trees . . . I’m calling life-sized nutcrackers, too.”

We resume our ambling, his arm curved around my lower back, my head nestled into his shoulder. Now that I’m thinking about it, it’s very tempting to snake my chilly hand into his back pocket. I could even cop a feel while I’m at it. “What do you do for Christmas?”

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