Chapter 31
The day of the trip finally arrived. The house buzzed with a kind of chaotic energy as everyone scrambled to get ready. Suitcases were being zipped shut, passports double-checked.
I was the first one fully packed and dressed, sitting on the couch with my backpack already slung over my shoulder. "Let's go already," I said, watching Alan shuffle between the living room and kitchen for the third time.
"Jake, we can't leave until your mother gets here," Alan said, trying to zip up his overstuffed suitcase. "She insisted on driving to the airport together."
"Because nothing says vacation like shared awkward silences," Charlie added, waltzing into the room in a Hawaiian shirt and sandals. "Who's ready for paradise?"
Alan raised an eyebrow at Charlie's outfit. "You do remember we're going to New York first, right?"
"Yeah, Uncle Charlie," I said, pointing at Dad, "we already have Dad to embarrass us. Let's not double down."
It wasn't a direct flight to Barbados. That part was my idea. Before heading to the Caribbean, we were stopping in New York City for six days. I'd never visited in my past life, and I wasn't going to miss the chance now. Museums, Wall Street, Central Park—I had a list, and I was ready to check it off.
"Thank you, Jake," Alan said flatly, clearly unamused.
"Fine," Charlie muttered, disappearing down the hallway to change out of his beach gear.
Judith arrived five minutes later, perfectly on time and already flustered. "Are we really doing this?" she asked, clearly still trying to convince herself.
"Yes," Alan replied, dragging his suitcase out the front door.
Evelyn showed up last, sunglasses on, wheeling a leopard print suitcase that screamed 'attention.' "Let's move it, boys. First class won't wait forever."
We all crammed into a large SUV that Alan had rented for the ride. Judith and Evelyn immediately started bickering in the back seat about which airline had better service, while Charlie—now in a normal outfit—blasted jazz from his phone and hummed off-key.
"Jake," Charlie said, glancing at me from the front passenger seat, "you sure this vacation is for you? Or is it just a social experiment in family dysfunction?"
"Honestly? A little bit of both."
Alan let out a long sigh toward Charlie. "Just try to enjoy it, okay?"
"I'll enjoy it when we're settled in the hotel and no one is yelling about who took whose seat in first class," Charlie replied.
Judith raised a finger. "That better not be a comment about me."
Evelyn didn't even look up from her compact mirror. "If the shoe fits, dear."
Charlie leaned closer and whispered to me, "Ten bucks says someone gets kicked off the plane before we even take off."
I smirked. "Only ten?"
As we pulled into the terminal at LAX, the atmosphere changed. Beneath all the sarcasm and passive-aggression, there was something else: anticipation. For me, this was more than just a family vacation—it was a step into a city I hadn't seen before.
We unloaded the luggage and headed toward check-in. Charlie tipped the skycap with a wink, Alan fussed with our boarding passes, and Evelyn tried to flirt her way into an upgrade.
"Gramma, the only upgrade we could get is a private jet," I pointed out.
"We should always try, Jake," Grandma replied, straightening her scarf like she owned the airline.
I looked around at this bizarre, chaotic group I called family. "Harper family vacation, phase one," I muttered as we walked through the automatic doors.
First stop: New York City.
Next stop: Barbados.
What could possibly go wrong?
———
Surprisingly, nothing did.
We landed at JFK without incident. No one got kicked off the plane. No in-flight drama. Not even a missing bag. It felt like we'd accidentally stepped into someone else's peaceful timeline.
The hotel was just as impressive as the brochure made it out to be—the Four Seasons. Elegant lobby, a view of Central Park, rooms that smelled like citrus and money. Evelyn looked around and declared it "acceptable." High praise, coming from her.
We spent the rest of the day playing tourists. We hit Times Square, took the Staten Island Ferry past the Statue of Liberty, walked through Central Park, and even eat at a food truck Alan picked after researching reviews for twenty minutes.
Alan bought one of those "I S2 NY" shirts. Evelyn complained that her heels weren't made for walking. Judith asked the tour guide at the Met if she had any coupons. And me? I soaked it all in.
It was my first time in New York. And for once, everything was... nice.
Too nice.
Almost suspiciously nice.
———
That evening at the hotel, everyone scattered. Judith went off to her massage appointment. Alan headed to the spa. Evelyn disappeared somewhere—probably the lounge, judging by the faint scent of martinis in the hallway.
I had just woken up from a nap when there was a knock on my door.
"Jake," came Charlie's voice. "I need your help."
I scoffed and sat up. "Of course you do. That was the only thing missing from today."
"Don't worry," he said, and I could practically hear the smirk. "It's not a twelve-year-old girl. She's beautiful. Like her mother."
I was already getting up to close the door on him when he added, "The Gilmore girls."
I froze.
I hadn't watched the show, but I remembered seeing clips online. The mother was stunning—sharp, funny, elegant. And the daughter? Cute, bookish, smart-looking. A different kind of beauty.
"What's her name?" I asked, cautious but curious.
"Lorelai Gilmore—the mom," Charlie replied, grinning. "And I think Rory for the daughter."
I narrowed my eyes. "You're not seriously telling me—"
Charlie smirked wider. "Come on. It's New York. Anything can happen."
"Okay, it's vacation, let's go," I replied, trying not to show too much enthusiasm.
———
Charlie led the way down the elevator and across the hotel lounge. He looked way too smug, like a man escorting royalty—which, in his mind, he probably was. When we reached the bar area, I spotted them immediately. Lorelai Gilmore, just as captivating in real life as she'd been in those clips I half-remembered. She had that effortlessly charming aura, like she was always on the verge of making a sarcastic joke. Rory sat next to her, looking far more subdued, eyes flicking between her mother and the menu.
"Jake, this is Lorelai," Charlie said with a wink. "And Rory."
I straightened up and stepped forward, offering a confident, slightly mischievous smile.
"Nice to meet you," I said smoothly. Then, turning to Lorelai, "You must be her sister?"
She blinked, surprised, then burst into genuine laughter.
"Well, aren't you a charmer," she said, clearly flattered. "That's one way to make a first impression."
I shrugged, still smiling. "Just calling it like I see it."
Charlie gave me a subtle elbow nudge of approval.
I turned to Rory and offered her the same charming smile, but dialed back a bit. "Jake Harper."
She looked up, polite but distant. "Rory Gilmore. Nice to meet you," she said before turning her eyes back to the menu, disinterested.
So... not impressed.
I blinked once, processing the lack of impact. My eyes twitched, then drifted to the ceiling, and I muttered just loud enough for Charlie to hear, "Really? Now it doesn't work?"
Charlie chuckled beside me. "Don't worry, champ. She's probably just playing hard to get."
Or maybe... maybe this time, I'd have to earn it.
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