Chapter 2: The Rules of Engagement

It was January 3rd. The world had exhaled its collective holiday cheer and settled into that gray, penitent phase where gym memberships are purchased and regrets are made.

The scent of pine was replaced by the smell of rain and stale coffee. It was the perfect atmosphere for drafting a document designed to prohibit happiness.

We met at a diner called "The Grind," which seemed fitting. Jackson was waiting in a booth, looking unfairly relaxed in a denim jacket, sipping black coffee. I slid in across from him, dropping my leather-bound notebook and a pen onto the laminated tabletop.

"You brought a weapon," he observed, nodding at the notebook.

"This is not a weapon, Jackson. This is the Constitution of our Platonic Agreement. We need to be specific. Ambiguity breeds feelings, and feelings," I tapped the notebook, "are our enemy."

He grinned, that easy, handsome flash that already felt too familiar. "Right. Before we start carving these commandments into stone tablets, let us confirm the details.

My goal is to stop my mother and grandmother from asking if I am dating that gorgeous, wealthy golf analyst who texts me about protein bars."

"And my goal," I said, leaning forward, "is to stop my entire family, specifically Aunt Susan, from setting me up with every divorced, recently separated man in the greater Chicago area, purely based on the fact that we are both vertical and breathing."

"The Holidate Pact," Jackson murmured, picking up my pen. "I like it. High-stakes emotional avoidance masked as a seasonal romance. I visit town occasionally for coaching and minor tournaments, so this works perfectly for me. There are no expectations and no long goodbyes.

"I travel a lot. Relationships do not really… stick."

"Excellent," I agreed. "I am a freelance copywriter. I craft emotional lies for money. I need someone to help me craft a convenient social lie for my family. This is business."

Two refills later, we were knee-deep in the world’s most dysfunctional relationship blueprint. The next hour was spent meticulously detailing the boundaries of our fake relationship. A conversation that felt much more intimate, and intense than any actual first date I had been on.

The Holidate Contract: Key Articles

Article I: The Calendar Clause.

Stipulation: The partnership applies only to major calendar holidays, family events, and weddings. Minor holidays, such as Groundhog Day, Arbor Day, and Tax Day, are not included.

Amendment: Must include birthdays, as family birthdays are often worse than Christmas.

Article II: The Feelings Filter.

Stipulation: There shall be no romantic feelings, emotional attachments, or discussions about commitment. If either party develops an actual feeling, they must immediately report it, and the pact is dissolved via the emergency exit clause.

Jackson's Addition: "Also, no unsolicited life advice. We are dates, not therapists."

Sloane's Addition: "Agreed. And no lingering eye contact that suggests depth. Keep it breezy."

Article III: The Physical Proximity Guidelines (PPGs).

Stipulation: Physical contact is strictly for public performance only. Acceptable actions include linking arms for photos, a quick cheek peck when greeting relatives, and emergency hand-holding when navigating crowded spaces (such as shopping malls or drunken weddings).

Jackson, scribbling: "No sleeping in the same bed. Ever. Even if it is the last room in the world."

"Duly noted," I said, trying to ignore the sudden warmth of the diner. "We stick to the script. We are committed, but not clingy."

Article IV: The Jealousy Buffer.

Stipulation: Both parties are free to date, hook up, or pursue genuinely interested third parties. There will be no questions, no judgment, and absolutely no jealousy. The Holidate is a temporary shield, not a claim.

Jackson looked up, pen paused. "I am serious about this one, Sloane. I need freedom."

"So do I," I replied, meeting his gaze steadily. I did not want to admit that the idea of him dating someone else already felt vaguely unpleasant, so I doubled down. "We are mercenaries. We do not get attached to the battlefield."

Finally, we reached the Emergency Exit Clause.

"If either of us needs to bail for any reason, a real emergency, a sudden opportunity, or, God forbid, we meet someone we actually like, we give twenty-four hours' notice," I summarized.

"And we never talk about this again," Jackson finished, capping the pen with a decisive snap.

We looked at the messy, detailed page of rules, written in my tight script and Jackson's looping handwriting. It was a beautiful, cynical testament to two people desperate to avoid vulnerability.

For two people so determined not to feel anything, we were putting an awful lot of care into our boundaries.

"We need a first date to set the stage," Jackson said, sliding the notebook back to me. "To confirm our cover story."

"New Year’s Eve, as per the contract," I confirmed. "And then Valentine's Day. After that, we coast until Easter."

"Wait," Jackson said, frowning slightly. "My golf coach is having his annual Post-Holiday Pre-Spring Thaw party this Saturday. It is technically not a holiday, but it is packed with people who know my mother, and I need a buffer from the Why do you not marry someone with a steady income interrogation."

I sighed dramatically. "A spontaneous, unscheduled Holidate. This is why contracts have addenda. Fine. But we stick to the PPGs. No accidental hand holding, Jackson."

He stood up, shoving his hands into the pockets of his jacket, and gave me that slow, charming smile again. "Deal. See you Saturday, Holidate."

He walked out first, leaving me sitting in the booth.

I stared at the notebook, which now contained the most carefully negotiated non-relationship of my life. I could not help but smile. It was perfect. Perfectly detached. Perfectly safe.

I picked up the pen and, on the bottom of the rules list, wrote one final, silent addendum:

Final Rule (Unwritten, For Sloane Only): Do not stare at the accent, or the hot body attached to it.

I underlined it twice.

As if that would help.