Ramona
I juggle my suitcase handle, fish out the phone, and answer mid-ring.
“Hey,” I say, stepping sideways so a cluster of cheerful sweater-wearing townsfolk can pass me on the sidewalk.
Hollyvale’s main street is decked out in green garlands, bright lights, and a huge wreath on an old-fashioned lamppost. It all looks suspiciously curated for a holiday card, like the entire town wants to remind me I’m behind schedule. “I just arrived,” I tell Brooklyn.
I close my eyes. “Brooklyn, I traveled overnight. The flight was delayed in Salt Lake, so I missed the last connecting bus—”
“Wait, that means you took a bus from some random stop? Did you get any sleep?”
I open my eyes again. The wind stings, and my ankles are officially numb.
“I can optimize for sleep later. Right now, I’m heading to the lawyer’s office to sign whatever final forms exist, get official ownership, and then list the property for immediate sale.
I’ll wire the money to the business account well before Christmas.
We’ll be flush again.” That’s the script.
I’ve said it so many times to myself that I almost believe it’s guaranteed.
Brooklyn sighs. “We have about eleven weeks of cash left, but the earliest we can land a bridging round is mid-January if everything lines up. That puts us roughly four weeks behind payroll if we don’t do something. Which means—”
“Which means I have to close the sale. I know.” My voice is a little sharper than I intend. “I’ll get it done.”
The street is so…charming that I almost resent it.
Every shop window brims with snowflake cutouts, candy canes, or blinking lights.
Across from me stands a café with a gingerbread house display in the window, looking far too delighted with itself.
I quickly redirect my attention to my phone.
“I’ll call you after the lawyer,” I say, then hang up before Brooklyn can detail yet another reason we need the money yesterday.
I navigate the street by memory, though I haven’t visited Hollyvale since I was a teenager.
The snow is deeper than expected, so I slow my pace.
My suitcase squeaks. My father never liked this place.
He said it smelled like pine needles and illusions.
He told me once that Grandma Iris left for a reason, that any small town that claims to be this friendly is a slow trap for gullible hearts.
I believed him for a while because I had no reason not to.
But I also vividly remember being seven years old, skidding across an old porch with the smell of sugar cookies drifting from the open window. That was a different version of me. A version who thought the best place on earth was inside a big warm house that smelled like something just baked.
My phone pings. Another text from Brooklyn:
Reminder: we NEED that sale.
Yes, yes, I know.
I push open the door to Carter & Associates, the law office handling Grandma Iris’s estate.
Immediately, the warmth of the building washes over me.
I stamp the snow off my boots on a mat that chirps, “Welcome to Hollyvale, happiest holiday town in Colorado!” Huh.
They have motion-activated doormats here? That’s…on brand.
An older woman behind the front desk gives me a bright smile. “You must be Ramona. I’m Carla. Can I take your coat?”
I shake my head, more rattled by the familiarity than the actual temperature. “I’m okay. Here to meet with Mr. Carter.”
“Of course.” She stands, and I notice a plush Santa figurine perched next to her keyboard. “He’s expecting you.”
Inside a wood-paneled conference room the size of my entire apartment’s living area, Martin Carter stands to greet me. He’s wearing a dark sweater vest, tie, and an apologetic expression. “Ms. Hale, so sorry to hear about your loss. Your grandmother was one of Hollyvale’s pillars.”
He gestures for me to sit. There’s tea, cookies, and a folder labeled BAINE ESTATE in front of him. I correct him automatically. “Actually, I go by my mother’s surname, Baines. But yes. Thank you.”
I expect him to give me papers, maybe a pen, and instruct me on the final steps. Instead, there’s a pause. He fiddles with the corner of the folder. “So. About Iris House—”
“I realize it’s in disrepair,” I interject, attempting to keep things on schedule. “She wasn’t able to maintain it after she closed it as a B&B. But I plan to sell as-is for a quick close. Is there anything else?”
His mouth goes thin. “Your grandmother left you the house in its entirety, yes.”
I exhale, relieved. “Good. That’s a big step. I’ll sign acceptance, possibly do a basic inspection so the buyer doesn’t run for the hills, and we can wrap in a week, two at most. I need the funds—”
He clears his throat. “I’m afraid there’s a…clause.”
I stop talking. Clauses are never good. Not in my experience. “What kind of clause?”
He adjusts his glasses. “Iris was quite involved in Hollyvale’s various traditions, especially the Twelve Dates of Christmas event.
In fact, she was a founding member for the app partnership with Matches Ever After—this, ah, holiday-themed dating experience they run in December.
If you’ve never heard of it, it’s a… local tradition.
People sign up to go on twelve holiday dates matched by the app, all culminating on Christmas Eve. ”
I blink twice. “Okay, but I’m not sure how that relates to the estate.”
His cheeks turn faintly pink, like he’s dreading the explanation.
“Well, your grandmother left instructions that you are to complete the Twelve Dates of Christmas—every single event—before December 24th. Only after you participate in this tradition can you formally take over Iris House and access the inheritance money.”
Time slows for a moment. I can actually feel my face freeze. “She wants me… to do a dating event?”
Carter glances at the folder as if it can bail him out.
“Yes. She wanted you to experience Hollyvale the way she felt it most. She also wanted to ensure you spent some actual time here. She was quite explicit: no partial attempts. You have to attend all twelve arranged dates, or the inheritance reverts to Plan B—some charitable trust, which she mentions in a letter but never gave details on.”
Shock hits me first, followed by a mounting wave of headache. “That’s not possible. I have a company to save. I’m here for the final signatures, not for some… extended courting fiasco.”
He swallows. “I’m aware this is unusual.
But the timeline is set. The app organizes the dates around specific holiday events: gingerbread contests, caroling, the cookie fundraiser, the market…
all culminating on Christmas Eve. If you complete them, the estate money transfers to you on December 24th, after the final date. If you don’t, it goes elsewhere.”
There’s a slow, cold pause in my chest. That money is the difference between my employees having job security or me telling them I can’t make payroll. That money is the difference between staying afloat or losing everything.
“How many days do we have until the first date?” I ask, my voice unsteady.
He checks a printout. “December 3rd is the gingerbread house event. Then each date lines up with a new Hollyvale tradition every other day or so. A few might cluster. It’s a condensed schedule. But you can’t skip any, or the contract is void.”
I do the mental math. “That’s three weeks of forced holiday events.”
Carter offers a helpless shrug. “It is exactly that. But if you stick it out, you’ll have full title on December 24th and can close the sale the next day, if your buyer is available. It’s the earliest you can do—maybe the 26th?”
He’s right. That’s a lost month for the startup. But if I walk away, we’re done for. “Fine,” I say clenched. “Twelve dates, three weeks, sign on the 24th, sell on the 26th.”
I grit my teeth. This is a puzzle, and I solve puzzles. I can handle one more puzzle, even if it’s humiliating.
“There’s more.” He grimaces. “She wrote a personal letter for you. I’m instructed to give it to you once you complete the final date. She said you’d… see why then.”
“Of course she did.” My laugh is humorless. It burns the back of my throat.
To his credit, Carter looks sympathetic. “I realize you might have complicated feelings about your grandmother. But it’s not my place to interpret her last wishes. I just carry them out.”
I push my chair back with a scrape. “Understood. Where do I sign for acknowledgment?”
He slides the relevant forms across to me, and I sign them with the pen he offers.
My handwriting is precise, controlled. My heart is not.
It’s pounding at the thought of explaining this to Brooklyn.
She’s going to flip. On the inside, at least—she usually keeps her voice calm the way I do, which means we’ll stew in silent panic together while trying to sound strategic.
Carter stands. “That’s all I need for now. The official app is called Matches Ever After. You’ll have to register yourself. They do everything electronically.”
“Right.” I gather my bag and suitcase. “Thanks.” Then I halt, one more question. “Does the house have heat, electricity—any chance I can speed things up by staying there? I might as well get it ready to show.”
“I wouldn’t advise it,” he says gently. “It’s been vacant a while. No staff, no maintenance. It will need repairs, and the insurance coverage might not be active yet.”
I nod once. “I’ll find a motel. I won’t be here long anyway.”
Outside, the wind slaps me again, and I weigh my next steps. Check into a motel, or at least find a place with Wi-Fi so I can see what I’m dealing with. That’s the more pressing concern.
I drag my suitcase over to a bench under a cheerful spray of colored lights and fish out my phone.
The screen struggles in the cold, but eventually I get the app store open.
A quick search: MATCHES EVER AFTER – “Find your holiday match, or let your holiday match find you!” The marketing line is truly ridiculous.