Chapter 2
Josh
The woman across from me at this upscale Manhattan steakhouse keeps staring at my hands like they might reveal the secrets of the universe.
The soft murmur of other conversations creates a backdrop that should be romantic but instead feels like a stage set for a performance for which I never auditioned.
Crystal glasses clink against each other at nearby tables, and the scent of expensive wine mingles with perfectly seasoned beef.
But all I can focus on is how Amelia’s gaze keeps dropping to my fingers as if she’s trying to imagine them around a pitchfork instead of a wine glass.
“So, you really milk cows every morning?” she asks for the third time, and her voice carries that breathy quality people use when they’re trying to sound impressed but mostly sound confused.
Something seems almost desperate in the way she’s clinging to this particular detail, like it’s the last thread connecting her fantasy to reality.
“Actually, we have automated milking systems now.” I cut into my ribeye while trying to ignore how she flinches every time I use my knife. “Most modern dairy operations do.”
“You still get up at dawn. Right?” She’s been asking increasingly specific questions about my daily routine ever since she arrived twenty minutes late, apologizing for traffic while clearly disappointed I wasn’t wearing a cowboy hat. “You, like, commune with nature and stuff?”
I set down my fork, wondering how this conversation went so sideways so quickly. “I get up early because that’s when work starts not because I’m communing with anything. It’s a business, not a spiritual retreat.”
She blinks at me with confusion, probably wondering why I’m not delivering folksy wisdom about the simple life or pontificating about the beauty of honest labor.
Her perfectly manicured fingers tap against her wine glass, and she’s barely touched her salmon.
The truth is, I run a successful agricultural operation that supplies organic dairy products to half the Northeast, employing forty-three people and managing a distribution network that spans six states.
But apparently, that’s too complicated for someone who showed up expecting a cowboy stereotype.
“Emma said you were more...rustic.” I hear actual disappointment in her voice, like someone might use when discovering their vacation rental doesn’t match the photos online.
Emma, my sister, apparently decided my dating profile needed creative enhancement without mentioning it to me.
I discovered this when Amelia arrived clutching a printout of photos that definitely featured me but also featured the prize bull I’d been showing at last year’s county fair, complete with my trophy for best livestock handling.
The photos made it look like I spend my days wrestling cattle instead of managing supply chains and reviewing quarterly reports. What the pictures didn’t show were the spreadsheets, the conference calls with distributors, and the minutia handled from a desk to make the operation successful.
“My sister has a very active imagination.” I take a long sip of my beer, wishing I’d ordered something stronger. “She also forgot to mention I have an MBA and spend most of my day on conference calls.”
The disappointment on Amelia’s face deepens, and I can practically see her romanticized fantasy crumbling in real time.
She’d probably imagined moonlit walks through pastoral meadows and heart-to-heart conversations about the meaning of life while sitting on hay bales.
The reality of farm management software and USDA compliance reports doesn’t quite match the dream.
“You still live on a farm.” Her voice carries desperate hope, like maybe she can salvage something from this evening.
“I live on agricultural property that happens to include my residence, yes.” I’m trying to be patient, but this conversation is wearing thin. “It’s not Little House on the Prairie. I have high-speed internet and everything.”
She laughs, but it sounds forced. “Of course, you do. I just thought it might be more...traditional.”
Traditional. Right. Like I should be churning butter by candlelight and speaking only in agricultural metaphors.
I’ve had this conversation before, with women who either want to save me from my “simple life” or who’ve watched too many romantic comedies featuring rugged men who need the love of a good city woman to complete them.
We soldier on through our entrees, both skipping dessert—her because she claims she has to watch her calories, and me to end this disaster faster.
The check arrives, and I reach for it gratefully because this date officially qualifies as a catastrophe.
Amelia makes a halfhearted attempt to split it, but her heart isn’t in the gesture.
She’s already mentally composing the story she’ll tell her friends about the farmer who turned out to be disappointingly normal.
“This was lovely.” She stands outside the restaurant, and we both know she’s lying. “Maybe we can do it again sometime.”
“Sure,” I lie back because honesty would require explaining I’d rather spend my evening reviewing feed contracts than pretending to be someone I’m not.
She gives me a quick hug that feels like a polite dismissal and then disappears into a taxi while I’m left standing on the sidewalk wondering why I bother with dating at all.
The city stretches around me, full of concrete, glass, and people who seem to know exactly what they want from life, even if what they want is apparently a fantasy version of me that doesn’t actually exist.
I walk back to my hotel, trying to shake off the frustration that’s become too familiar lately.
I pay attention to the city in a way I rarely do when I’m focused on business meetings.
The architecture here tells stories of ambition and reinvention with buildings reaching skyward like they’re trying to escape the limitations of ground level. Maybe that’s what I need to do too.
This is the third date in two months that’s gone sideways because of preconceived notions about what my life should look like. Either they want to rescue me from rural isolation, or they want me to be some kind of noble savage, who finds meaning in physical labor and speaks in weather metaphors.
Back in my room, I pour myself a drink from the minibar and stare out at the Manhattan skyline while contemplating the care package Emma had waiting for me on the counter when I arrived.
It contained some optimistic things, like a bottle of champagne and some chocolates, and some less optimistic things.
I haven’t really dug into it yet, but I move toward it now.
The care package contains articles about “successful rural relationships,” a book called Finding Love After Thirty: A Rancher’s Guide, and a business card for something called Romance Expected Dating Service.
Someone had taken care to print out what I can only assume is Emma’s message at her direction, placing it on the card with a Post-it. “Just try it.”
I pick up the business card now, turning it over in my hands.
The cardstock feels substantial, not the flimsy kind that businesses use when they’re cutting corners.
Red Carrington, Professional Matchmaker.
Something about the simple design appeals to me.
There are no hearts or cutesy fonts. It’s just clean typography that suggests competence rather than romantic fantasy.
The back has a simple tagline: “Authentic connections for complex people.”
Emma’s been dropping hints about this place for weeks, ever since her friend got married to someone she met through their service.
“They specialize in people who don’t fit traditional molds,” she’d said, which at the time sounded like code for “weird people who can’t date normally.
” Now, I’m wondering if maybe she had a point because traditional dating certainly isn’t working for me.
I check the time. It’s past business hours, but their website mentions video consultations available until nine p.m. That date didn’t even make it until eight, so I still have some time.
The website itself is refreshingly straightforward with clear information about their process and a photo of a woman with red hair, kind eyes, and an honest smile wearing a red kaftan.
Before I can talk myself out of it, I’m dialing their number and hoping I don’t get voicemail.
The voice that answers is warm and professional, sounding genuinely interested rather than reading from a script. “Romance Expected, this is Red.”
“Hi, this is Josh Brennan.” I settle into the hotel chair and hope this doesn’t turn out to be another waste of time. “My sister Emma recommended your service, though I should probably mention upfront that I’m calling from a hotel room after a spectacularly bad date.”
Red chuckles, and she sounds sincerely amused rather than politely sympathetic. “Those are actually my favorite calls because honesty born of frustration tends to be the most useful variety. Tell me about the spectacularly bad date.”
“She showed up expecting a cowboy and got a businessman who happens to work in agriculture.” I’m surprised by how easy it is to talk to her and how her voice seems to invite honesty instead of performance.
“Apparently, my sister enhanced my dating profile with some creative photography that might have given the wrong impression.”
“Ah, the well-meaning family member who thinks they know what you need better than you do.” Red’s tone suggests this isn’t news to her. “Let me guess. She either wanted to save you from your simple life or turn you into her personal fantasy of rural authenticity.”