Page 4 of It's the Worst Time of the Year

JACOB

I always hated flying.

The cramped seats, the too-loud hum of the engines, the inability to move—it all grated on me. Even with my noise-canceling headphones and a decent view from the window, the flight from Chicago to Bozeman felt endless. The turbulence didn’t help either; every jolt and shudder seemed designed to test my patience.

But the flight itself wasn’t the problem. My real issue sat neatly folded in the briefcase under my seat, along with the case files for the Barrington property dispute. It wasn’t the legal complexities or the tight timeline that gnawed at me—it was a name…

Bailey Pace.

Seeing her name on the opposing counsel list had been a punch to the gut. It had been years since I’d last seen her, but her name brought everything rushing back: the good, the bad, and all the unresolved feelings I thought I’d buried.

The plane dipped slightly as the captain announced we were preparing for landing. Outside the window, a stretch of white clouds gave way to snow-covered peaks. The vastness of Montana was striking, even from the air. Rugged, untamed, and sprawling in a way that made Chicago’s gridlock feel laughable.

I shifted in my seat uncomfortably, trying to ignore the ache in my back from sitting too long.Focus, Jacob. This is just a case. It doesn’t matter who’s on the other side of the table. But the rational part of my brain couldn’t override the memories that had come flooding back the moment I saw her name.

Bailey Pace...The girl I once thought I’d spend forever with. The woman who walked away from what could have been when we couldn’t reconcile our dreams. Fate sure had a funny sense of humor for bringing us together again in this way—at Christmas, no less.

The plane touched down with a jarring bump that matched my sour mood.

Bozeman’s airport was small and efficient, a far cry from the chaos of O’Hare. I weaved through the crowd of travelers bundled in puffy coats, dragging my designer suitcases across the linoleum floor. After a brief stop at the rental counter, I found myself holding the keys to a basic sedan.

“Wintervale?” the rental agent asked brightly as she handed me the paperwork.

I nodded curtly, straightening the sleeves of my overcoat. “That’s right. I get the pleasure of spending my holiday this year working on an important legal matter in the middle of the boondocks.”

Her smile had the faintest trace of pity. “Well, it’s a beautiful drive this time of year. The snow makes everythinglook like a postcard. Maybe you’ll change your mind about Wintervale by the end of your trip.”

I chuckled, shaking my head before thanking her and making my way to the car, where I tossed my bag into the backseat and slid behind the wheel. The cold hit me immediately, sharp and biting, even inside the vehicle. I let the engine warm up while fiddling with the GPS, punching in the address for the Wintervale Resort.

The drive started uneventfully, the highway cutting through open fields blanketed in fresh snow. Gradually, the landscape transformed. Mountains rose in the distance, their peaks disappearing into the low-hanging clouds. Forests of evergreens stretched on either side of the road; their dark green needles heavy with white.

Despite the breathtaking scenery, my thoughts were anything but calm.

Bailey Pace...Her name refused to leave my mind, like a song on repeat.

We’d met in high school, two ambitious, middle-class kids from a small suburb of Seattle who dreamed of something bigger. She wanted to be a lawyer. So, did I. We bonded over late-night study sessions, mock trial tournaments, and whispered conversations about the future.

But when the time came to leave, our dreams diverged. I was desperate to escape the confines of where I’d grown up, to carve out a new life somewhere far away from my alcoholic father and the chaotic household of my childhood. Bailey, on the other hand, wanted to stay close to home, near her family and the roots she’d planted.

In the end, we couldn’t reconcile our paths. I left to attend university in Chicago, and she stayed behind. The breakup wasclean—amicable, even. Or at least, I’d thought so at the time. But it left a scar I hadn’t dared to examine too closely ever since.

Now, years later, she’d come back in my life, attached to a case that had brought me halfway across the country.

By the time I reached Wintervale, the sun was low on the horizon, and a soft golden glow hung over the snow-draped town.

The sign welcoming me to the village was quaint, painted in cheerful red and green with the wordsA Place to Call Homescripted underneath. The town itself looked like something out of a Christmas movie. Twinkling lights stretched across the main street, and every storefront was adorned with garlands and wreaths.

It was the kind of place that would’ve charmed Bailey instantly, and I felt an odd pang in my heart.

The ski resort that the town was best known for sat on the outskirts of the city, perched on a small hill overlooking the village. Its elegant stone façade was draped with icicle lights, and I spied a gigantic Santa Claus sitting in a sleigh piled high with gifts in one of the huge bay windows on the upper floor.

I chose to park the car myself in the lot, even though the firm was covering the expense of the rental. I never trusted valets not to ding the paint of my luxury BMW back at home, and I didn’t feel right giving up the habit just because someone else was footing the bill. After grabbing my bag, I made my way inside the hotel as my boots crunched against the packed snow. The warmth of the lobby covered me instantly like a blanket, carrying with it the scents of pine and cinnamon. A massive fireplace crackled in one corner, and the flickering light from the hearth cast soft shadows across the polished wood beams.

“Mr. Wilder?” The receptionist greeted me with a smile. “Welcome to the Wintervale Resort. Your room is on the second floor, overlooking the slopes. If there’s anything you need during your stay, don’t hesitate to let us know.”

“Thanks,” I said, taking the keycard the clerk handed me.

The lobby bustled with activity as it was around dinner hour. Families huddled near the fireplace, sipping mugs of hot cocoa, while couples admired the towering Christmas tree in the center of the room.

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