12 Dates Till Christmas

I did it.

I actually did it.

I signed up for the town’s “12 Dates of Christmas Challenge” like a sane, stable, emotionally available adult. Which was a complete lie, because I was a Christmas-obsessed, hopeless romantic with a glitter addiction and a worrying tendency to cry during Hallmark commercials.

I hugged my coat tighter as I walked away from the town library, the winter wind nipping at my cheeks like it had a personal vendetta. The clipboard still clutched in my gloved hands bore the unmistakable scrawl of my signature, inked with both holiday spirit and blind optimism.

This was either going to be magical… or a complete disaster.

Probably both.

The challenge, a now-infamous December tradition in our little town of Winter Hollow, was part small-town matchmaking experiment, part social media circus. Twelve dates with twelve different mystery couples, all leading up to the big Christmas Eve Gala. Each date would be “casually” documented by nosy locals and voted on for entertainment. No pressure.

“Love and local business exposure!” the poster had promised. “Festive fun and maybe romance!”

Emphasis on maybe.

I turned down the snow-dusted path toward Anna’s house, my boots crunching with satisfying Christmas movie sound effects. The cozy yellow cottage came into view, twinkling with fairy lights and smelling vaguely of cinnamon and ambition.

I knocked three times—our childhood secret knock, because we were those best friends.

The door flew open, and there she was: Anna, wearing a reindeer onesie and a candy cane headband like the sane, mature woman she was.

“I signed up for the 12 Dates.” I blurred out with no warning.

“YOU DIDN’T,” she gasped.

“I DID.” I held up the entry certificate like a golden ticket.

She screamed.

We screamed.

There may have been jumping.

“You maniac!” Anna grabbed me by the arm and pulled me inside. “Come in before you get frostbite and regret your entire life.”

I toed off my boots and followed her into the warm, fairy-light-covered living room. The fireplace crackled, and the whole house smelled like peppermint hot cocoa and the faint, distant memory of college heartbreaks.

Anna handed me a steaming mug of cocoa with three marshmallows—three, because she knew I didn’t trust even numbers in beverages—and we plopped down on her couch, still riding the high of my poor life decisions.

“So.” She sipped her cocoa, eyes sparkling. “Tell me everything. Did they ask any weird questions? Are you going to have to bungee jump with a stranger dressed as Santa? Is it a dating show or an emotional Hunger Games?”

“I don’t know,” I laughed. “They just had me fill out a basic form—name, age, favorite Christmas movie—”

“The Holiday, obviously,” she interrupted.

“Obviously,” I agreed, tapping my mug against hers. “And then they said the matches would be randomized, the dates would be filmed—”

“Filmed?” Her eyes widened. “Like filmed-filmed?”

“Yeah, but like… recorded by locals. Or whoever’s around. They want ‘authentic Christmas chaos.’” I made air quotes.

“Oh good. I love when romance meets public humiliation.”

“Right? But also, like, charming public humiliation. In a sparkly scarf.”

Anna grinned. “You’re going to be amazing. Or go viral. Or both.”

“Thanks for the faith,” I said, then sighed. “But seriously, I needed this. My last ‘holiday romance’ was with a guy who gave me a gift card to a tire shop and told me to ‘treat myself.’”

She choked on her cocoa. “To… a tire?”

“He said it was ‘practical.’” I stared into my marshmallows with the weight of all my past romantic failures. “This year, I want mistletoe. I want movie montages. I want—”

“—someone who doesn’t think Goodyear is a love language.”

“Exactly.”

Anna leaned her head on my shoulder. “Well, you’re going to crush this challenge. And even if your dates are weird, at least they’ll be festively weird.”

I laughed. “I can’t even guess who else signed up. Probably half the town. Or that guy who runs the candle shop who’s always talking about ‘scents and sensuality.’”

“Or Mrs. Bloom’s grandson who thinks he’s a TikTok star,” Anna offered.

“Oh no. No no. I draw the line at shirtless caroling.”

She wiggled her eyebrows. “What if it’s someone unexpected?”

“Like…?”

She shrugged mysteriously. “You’ll see. But whoever it is, they better be ready for Estella ‘Ella’ North and her Christmas juggernaut of joy.”

I took a long sip of cocoa. “They better also like gingerbread, because I will be judging their structural integrity during the contest date.”

“Atta girl.”

I smiled into my cocoa, the marshmallows almost melted down into a sugary swirl.

“So,” I said, nudging her shoulder with mine. “What about you, future Mrs. Festivity? How’s Brian?”

Anna’s entire face lit up like a tree in Rockefeller Center. It was honestly rude how in love she looked.

“He’s great,” she said with a dreamy sigh. “He’s actually out with my brother right now, grabbing something from the hardware store or—I don’t know, doing guy things. Probably comparing beard trimmers and pretending they know how to fix stuff.”

At the mention of her brother, my smile faltered.

Ugh.

“Your brother,” I muttered, trying not to gag on my marshmallow. “Delightful.”

Anna snorted. “Oh come on. Don’t act like Estella North and Grayson Miller aren’t secretly obsessed with each other.”

I dramatically clutched my cocoa. “I am not obsessed. I am afflicted.”

“He’s not that bad,” she said through a grin.

“He hates Christmas.”

“Okay, that is bad,” she admitted, giggling.

“And he once called my tree skirt ‘a fabric donut of dysfunction.’”

“It was glittery plaid with fringe.”

“It was festive! And also vintage! Thank you very much.”

Anna laughed so hard she almost spilled her drink. “You two have more chemistry than a Hallmark baking competition.”

“No,” I said flatly. “We have history. Very specific, highly combustible history involving a ruined sixth-grade Christmas play and a snowman decapitation.”

“You still bring that up like it was a crime.”

“He punted Frosty’s head into the orchestra pit.”

“It was papier-mâché!”

“Frosty had a soul, Anna.”

She wiped a tear from her eye, still cackling. “You are so dramatic, I love it.”

“I demand a change of subject before I start rage-decorating your house.”

“Fine, fine,” she said, still grinning. “When do you find out who you’re dating?”

“Tomorrow,” I said, exhaling. “The list gets posted in the town square at noon. Like a festive Hunger Games reaping, but instead of death it’s potential emotional devastation and carolers.”

Anna raised her mug. “May the dates be ever in your favor.”

“Thank you. I fully expect at least one date where the guy is in a Santa suit.”

She burst into laughter again. “You know what? I can picture it.”

I groaned. “I know.”

“See? You’re desperate.”

“Desperate,” I agreed, sipping dramatically. “But optimistic.”

We settled into the kind of easy, bubbly chatter we’d always had—silly stuff about holiday traditions, bad first dates, our childhood Christmas crafts (I once glued cotton balls to my own sweater and called it a snowstorm), and how I was still bitter about losing the fifth-grade Christmas cookie bake-off to a kid who used store-bought dough.

Time slipped by in cozy warmth, laughter weaving through the room like tinsel on a tree.

Eventually, Anna clapped her hands. “Movie time?”

“Only if it’s The Holiday,” I said.

“Obviously.”

She turned on the TV, queued it up, and we curled up with a blanket as the opening music played. Just as Cameron Diaz was fake-crying in a mansion, the front door opened.

“Babe, I’m back!” Brian’s voice called.

“In the living room!” Anna answered, her voice already full of that glowy, gooey love tone she got whenever he was around.

Brian stepped in, dusted with snow, cheeks pink from the cold. He was tall and handsome in that cozy golden-retriever way, with warm eyes that always landed on Anna like she was the only person in the room.

He leaned down and kissed her softly, his hand lingering on her cheek. “Miss me?”

“Always,” she whispered.

I looked away, hiding my smile in my cocoa. My heart did this weird little twist—not jealous, not bitter. Just… aching a bit.

I wanted that.

I wanted exactly that.

Someone who looked at me like I was the most magical thing about Christmas. Someone who wanted cocoa and chaos and twinkling lights and every messy, sparkling part of me.

But for now… I had twelve strangers and a hope.

And that was enough.

For now.