Chapter 4: New Year's Debacle: The Test Run

New Year’s Eve. The most aggressively hopeful, and therefore most aggressively disappointing, night of the year.

It’s when the entire planet pretends that a clock striking twelve magically cures all their bad habits and loneliness. And tonight, it was the official start of the Holidate Calendar.

We were attending a black-tie gala organized by my brother Peter’s law firm. It was a formal parade of perfectly matched couples, expensive champagne, and strained elevator pitches.

Jackson looked phenomenal. He was wearing a classic tuxedo that hugged his shoulders in a way that screamed “successful, emotionally stable human.” He even managed to make the required black bowtie look effortless.

“We need to discuss the strategy for the midnight clock,” I instructed, adjusting the silver necklace Jackson had loaned me, a piece of "performance jewelry" as per the contract.

“The strategy?” Jackson raised an eyebrow, handing our coats to the attendant.

“Yes. According to Article III, physical contact is strictly a public performance only. Midnight is the most public performance moment of the year. If we don’t kiss, we look like a sham. If we do kiss, we risk violating Article II, the Feelings Filter, through excessive emotion transfer.”

Jackson laughed, a low rumble that always made me forget my complex algorithms for a second. “I think the risk of the crowd believing we don’t want to kiss is higher, Holbrook. We’re supposed to be in the honeymoon phase.”

“Fine. We’ll do the ‘Quick Press’,” I decided. “Zero tongue, minimum lip contact. Just enough to look enthusiastic and get the camera flashes to stop.”

We spent the next two hours navigating the dense crowd, a masterful display of teamwork. Jackson introduced me as his serious girlfriend, Sloane, the brilliant freelance writer, and I introduced him as my serious boyfriend, Jackson, the successful golf coach, subtly implying he was rich and always on the move, which excused his general absence.

The family arrived fashionably late, which was exactly when the trouble began.

“Sloane, darling!” my mother, Elaine, swooped in, radiating joy. Her eyes immediately locked onto Jackson. “You two look radiant. Jackson, you look like a magazine cover. Is that real silk?”

“Only the finest for your daughter, Elaine,” Jackson replied smoothly, holding my hand precisely as long as was necessary to seem devoted, and no longer. “Sloane insisted I buy it.” A lie, but an excellent one.

The inspection continued as Peter and his wife, Jessica, joined us. Peter, ever the suspicious lawyer, interrogated Jackson about his golf coaching schedule with the intensity of a cross-examination.

Jackson, however, was charming, deflecting questions about commitment with talk of international tournaments, thereby satisfying my mother’s need for prestige and Peter’s need for complicated logistics.

Everything was going perfectly until a woman approached us, a tall, elegant blonde who was clearly not a part of Peter’s law firm.

“Jackson!” she said, her voice sharp with surprise. “It is you. I heard you were back in town. You didn’t return my calls.”

Jackson’s easy smile flickered. “Veronica. Happy New Year. This is Sloane, my girlfriend. Sloane, this is Veronica, an acquaintance.”

Veronica’s gaze raked over me, settling dismissively on my loaned necklace. “Girlfriend? Since when, Jackson? Since Christmas Day? Last time we spoke, you were quite clear about avoiding attachments.”

The air thickened. My mother looked horrified, Peter looked intrigued, and I felt a faint, annoying prickle of defensive anger. Veronica was trying to expose Jackson’s aversion to relationships, and by extension, expose me as a fraud. I couldn’t allow it.

I leaned into Jackson, resting my hand lightly on his chest, a minor PPG violation, but necessary for cover.

“Oh, Veronica, we know,” I said warmly. “Jackson’s commitment phobia was hilarious at first. He tried to dump me twice before Christmas just so he could spend New Year’s with his golf clubs. But I’m persistent. We worked through it. We’re happy now, right, honey?”

I gave Jackson a look that clearly communicated: Go along with this, or I will use my copywriter skills to ruin your reputation among the Holbrooks forever.

Jackson recovered instantly, his arm wrapping around my shoulders, drawing me close. His breath was warm against my ear. “Absolutely. Sloane’s tenacity is what I love most about her. She’s the boss, always.”

Veronica blinked, clearly expecting denial, not this unified, mildly sarcastic front. She stammered a quick, “Well, I’m happy for you,” before retreating into the crowd.

My mother watched Veronica walk away, then turned to us, her face a mask of satisfaction. “Oh, Sloane. You found a man who is as stubborn as you are. It’s a New Year’s miracle!”

The clock began to chime.

Ten seconds.

Nine.

Jackson and I looked at each other. The performance had just gotten real. We had successfully defended the pact, but the adrenaline of the confrontation was still humming between us. We were standing too close, and the noise of the countdown felt deafening.

Eight.

Seven.

Jackson’s hand drifted from my shoulder to cup my cheek. He didn’t look charming; he looked focused. He looked sincere.

Six.

Five.

“Forget the Quick Press,” he murmured, his voice low, just for me. “We earned this.”

Four.

Three.

His lips found mine at the moment the crystal ball dropped. It wasn't the chaste, professional peck we had negotiated. It was long, firm, and undeniably sweet. A kiss that tasted like expensive champagne and adrenaline. A kiss that felt less like an act for the crowd and more like a period ending a very complicated sentence.

The crowd cheered. The camera flashes blinded us. When he finally pulled back, his thumb brushed my cheekbone.

"Happy New Year, Holidate," he whispered, his eyes sparkling in the confetti light.

“Happy New Year,” I managed, my heart hammering against my ribs. I felt flushed and a little dizzy. That kiss was a blatant violation of every single rule we had written. Passionate. Emotional. Meaningful.

But standing there, watching my entire family beam at us with relief and pride, I realized that for the first time in a very long time, I hadn’t felt alone at midnight.

And that, I thought with a terrifying little twist in my stomach, was going to be a problem.