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Chapter 6: Cupid’s Cruel Joke
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2025-11-22 03:33:11
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The Holidate Pact Chapter 6: Cupid’s Cruel Joke
February 14th. Valentine’s Day. If Christmas was the Olympics of Judgment, Valentine’s Day was the Super Bowl of Single-Shaming. It was a mandatory event for the Holidate Pact, but tonight, the event was not for my family. It was for my co-worker, Beth.“You’re doing a fantastic job, Jackson,” Beth gushed, leaning across the faux-marble table at the aggressively romantic Italian restaurant. “You’re just so normal. My last date spent the entire evening explaining the economic impact of NFTs on vintage Pokémon card collecting.”Jackson gave his practiced, charming smile. “Just happy to be here. Sloane’s an excellent human. She makes a man want to stick around.”The lie felt less like a protective shield and more like an itchy wool sweater. Beth had organized a disastrous double-date, pairing me and Jackson with her newly engaged sister and her sister’s fiancé. The conversation had predictably devolved into a detailed explanation of their wedding registry.“We settled on the slate gray t
The Holidate Pact Chapter 5: Susan’s Wisdom
The Monday after the New Year’s kiss was a masterpiece of emotional denial.Jackson and I had a brief, clinical text exchange. It went like this:Jackson: Midnight performance review: 10/10. The crowd believed it. Mission accomplished.Sloane: Agreed. High marks for lip-syncing enthusiasm. Protocol restored.Jackson: Good. See you Sunday for the brunch. Keep your focus, Holidate.He never mentioned the way the kiss had lasted slightly too long, or the way my hands had gripped the silk of his lapels, or the brief, terrifying spike of genuine feeling that had momentarily dissolved the champagne haze.We had both agreed to treat the event as a tactical necessity, a successful deployment of the Physical Proximity Guidelines (PPGs) to prevent the greater tragedy of family pity.When Jackson arrived at the Holbrook house for the Sunday brunch, he was not just on time; he was early, bearing a beautifully arranged fruit platter that looked suspiciously professional."He brought fruit," my mot
The Holidate Pact 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 conta
The Holidate Pact Chapter 3: The Pre-Spring Thaw (And How We Avoided It)
I stared at myself in the mirror. I was wearing a black dress that was aggressively professional. The kind of dress that says, "I am here to network, not to accidentally catch feelings." This was key because the last thing I needed was to turn up at a golf coach's party looking like I was actually trying to date a golfer.Jackson’s coach, a man named Coach Hayes, lived in a sprawling house north of the city. It was the kind of place that smelled faintly of money, leather, and disappointment. When Jackson opened the door to his car, I felt an instantaneous rush of theatrical comfort."Ready to execute the mission, Holidate?" he asked, his Australian accent low and conspiratorial. He looked impossibly good in a simple navy blazer. The kind of look that immediately invalidates Rule V (No staring at the accent, or the person attached to it)."As ready as I will ever be to pretend to have a functioning relationship in a room full of people who think matching polo shirts are haute couture,"
The Holidate Pact 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
The Holidate Pact Chapter 1: The Curse of Christmas Past
The first mistake I made was agreeing to wear the elf costume.It was December 25th, 10:00 AM, and I was pinned between my mother, Elaine, who was beaming maniacally, and my younger sister, Daisy, who was live-streaming our descent into seasonal madness on Instagram. We were standing in the middle of my parents’ overly festive living room, a room that currently smelled of pine, passive aggression, and burnt sugar cookies, and I was wearing green velvet leggings and a tunic with tiny jingle bells sewn onto the collar.“Say cheese, Sloane!” Mom chirped, adjusting the pointed hat that was currently digging into my scalp.“I’d rather say ‘I quit’,” I muttered, wrenching myself free. “I’m a thirty-five-year-old woman. I should not be dressed as a supporting cast member from the North Pole.”“Don’t be such a grinch, honey,” my brother, Peter, called from across the room. He was currently wearing a respectable cardigan and an expression of smug marital bliss as he handed his wife, Jessica,
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