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Story: The Layover that Changed Everything (The Meet Cute #1)
The Chicago Trip
Song : Nevermind - Dennis Lloyd
I landed at O ’ Hare just before noon, and for the first time in a long time, I felt…
calm. Not bored. Not numb. Just calm. The usual swirl of thoughts didn ’ t rush in to greet me the second I stepped off the plane.
It was like the Chicago air carried some kind of chill I welcomed.
A clean slate. The snow hadn’t started falling yet, but the sky was heavy and gray as I made my way to the ride-share pickup, coat zipped high, fingers tucked deep into my sleeves.
Rockford wasn’t exactly close to the airport, but I liked being tucked just outside of the chaos.
I needed this trip to be a little slower.
A little softer. So I sat back in the Uber, watched the trees blur past, and tried not to think about much of anything.
The Airbnb I booked was a gem—modern, warm, and stocked like a liquor store.
A whole wall of shelves with whiskey, gin, vodka, and even a few imported bottles I couldn’t pronounce.
Whoever owned this place knew how to host. I dropped my suitcase by the door, peeled off my boots, and took a moment to just stand there.
Quiet. Alone. Free. It started snowing just as I unpacked.
Big, fluffy flakes that fell like confetti.
I curled up on the oversized couch with a blanket, turned on the fireplace, and started a rom-com marathon.
I let myself unwind—no schedules, no decisions.
Just warmth, movies, and the low hum of snowfall outside the window.
The next day—Friday—I took the train into the city, determined to play tourist for once.
I visited Millennium Park, took selfies with the Bean, and laughed at myself for acting like such a cliché.
I bought keychains, fridge magnets and a snow globe I didn’t need.
And then I splurged on a birthday dinner at The Capital Grille.
Alone. They gave me a candle in my dessert and sang softly like they weren’t sure if I’d start crying or dancing.
I did neither. I just smiled, thanked them, and toasted myself.
To thirty-three. To freedom. To find something that felt like home.
After dinner, I wandered through the city, letting the cold slap some life into me.
My cheeks were pink from the wind, and my fingers were stiff despite my gloves.
I found myself at a little upscale spot called Maple pouty lips, but not try-hard—and I texted him:
“Hey, you. Remember me?”
Seconds turned into minutes.
Then came the reply:
“I don’t know who you are.”
I stared at the screen, blinking.
Was he joking? Was this some kind of flirty amnesia thing? Or did he seriously not remember?
“Never mind. I guess I’m not memorable,” I replied, fingers trembling with embarrassment. I threw the phone across the couch, groaning loud enough to scare the dog I didn’t have with me.
What the fuck ?
Had I hallucinated that connection? Was I so love-starved that I’d imagined the whole thing?
I curled deeper into the couch, pizza in one hand, a bottle of Fireball in the other.
I loved cinnamon whiskey. But it hated me back in a way that made me feel less alone.
The rest of the night was a blur of vampire romance, drunk scrolling, and stupid tears I refused to acknowledge.
I texted no one. Called no one. I just drank until the bottle was too light to hold and passed out on the couch in a tangle of supreme pizza crust and regrets.
The next morning was a crime scene. Fireball bottles.
Pizza boxes. My pride shredded somewhere under the coffee table.
I dragged myself into the bathroom and washed the smell of cinnamon and shame off me, vowing never to drink that poison again.
I bundled up, grabbed a hot coffee, and went back into the city.
Despite the freezing wind and aching head, I toured a few apartments downtown—lofts with exposed brick, quiet corners with Chicago river views, and overpriced shoeboxes that promised “urban charm.” I wasn’t ready to sign anything.
But I needed to see if this place could be it.
Could be home. Surprisingly… I liked it more than I thought I would.
There was something gritty about Chicago that made me feel real.
Like I didn’t have to smile all the time. Like I could just exist here.
That night, I found a cozy Irish pub on the corner near the Airbnb.
It was dark, warm, and smelled like Guinness and comfort.
The bartender reminded me of someone’s grandpa, and the jukebox played classic soul all night.
I sipped a whiskey (not Fireball), and let the heat soak into my bones, and it felt…
good. Just good. No Jon. No expectations.
No old ghosts. When I got back to the Airbnb, I packed slowly, folding each shirt as it mattered.
Tomorrow, I’d head back to Houston. One last straight flight.
No layovers. No flirtatious strangers. Just me, my bags, and my weird depressing life with my 2 cats and tiny dog.
I woke up early the next morning, refreshed for once, and even excited to see my little dog Nacho.
I missed that boujee little furball like crazy.
My cats were still in Fort Worth with my best friend Christine, who had offered to keep them while I figured things out in exchange for a 2 bedroom townhouse that wasn’t near her son’s father.
She didn’t ask questions. Just said, “Take your time. I got them.” She always understood. That’s why she was my best friend.
The Uber ride to the airport was smooth.
I had my United Club pass, so I planned to lounge, eat, and enjoy my two free drinks.
But Chicago’s airport is a beast, and I wasn’t about to make the rookie mistake of relaxing before finding out if my actual gate truly existed.
Once I confirmed I wasn’t boarding from some alternate universe terminal, I headed to the lounge.
Lunch was incredible—real food, not sad peanuts—and the drinks were strong.
The perfect sendoff. I watched people bustle past, wondering where they were running off to.
Wondering what it would feel like to have a one-way ticket somewhere and not be afraid.
The flight home was uneventful. I watched a movie, drifted off for a bit, and woke up as we touched down at George Bush Intercontinental Airport.
Storms had rolled through while I was in the air, so traffic was a mess, but I didn’t care.
I was almost home. Sort of. My parents were still at work when I arrived, so I let myself in with the spare key.
The house smelled like curry and candles.
I raided the fridge for leftovers—chicken pelau and some fried plantains, the good stuff—and reheated a plate before heading up to my old room.
I didn’t even bother changing clothes. I just kicked off my boots and climbed into bed, only to be greeted by a soft woof and two tiny paws hopping up beside me. Ranger.
My mom’s dog now, but once mine. He used to whine every time I left him alone.
Had to sleep right next to me or he’d panic.
I gave him to her because I knew she’d be home more, but every time I visited, it was like nothing changed.
He curled up beside me, head resting on my stomach, eyes already closing.
Nacho climbed up next, licking my hand like I’d been gone for years instead of days.
I scratched behind his ears and let the comfort wash over me.
This trip hadn’t solved everything. I still didn’t know where I belonged.
Still didn’t know what came next. But I knew one thing.
I wasn’t going back to the old me. And even if Jon didn’t remember me—or pretended not to—I remembered who I was when I met him.
And maybe that version of me deserved a second chance.
Whether it was in Chicago, or somewhere else entirely, I’d keep searching.
And until then? Nacho. Ranger. A warm bed. And no more Fireb all.
Table of Contents
- Page 1
- Page 2
- Page 3
- Page 4
- Page 5 (Reading here)
- Page 6
- Page 7
- Page 8
- Page 9
- Page 10
- Page 11
- Page 12
- Page 13
- Page 14
- Page 15
- Page 16
- Page 17
- Page 18
- Page 19
- Page 20
- Page 21
- Page 22
- Page 23
- Page 24
- Page 25
- Page 26
- Page 27
- Page 28
- Page 29
- Page 30
- Page 31
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- Page 36
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- Page 38
- Page 39