My date was thirty minutes late, which gave me thirty minutes to realize three things:
1. My shoes were already a mistake.
2. The waiter had definitely judged me for ordering wine alone.
3. I was, once again, about to waste an evening on the wrong man.
The shoes first. Nude stilettos, discounted price, allegedly "classic." Classic, as it would subsequently prove, the kind of classic medieval torture devices are classic. They pinched, they creaked, and I was ninety percent certain that by dessert I would need my toes amputated.
The guy number two. Adrian. We'd met on an app where he'd touted himself as "laid back" and "fitness-oriented." Translation: he'd posted gym selfies halfway around his body and mistaken the word brunch for a personal adjective.
Finally, the wine. I was halfway through my second glass when Adrian arrived, breathing hard, hair gel glinting like a warning sign.
"Sorry I'm late," he said, sliding into the chair opposite me. "Traffic was insane. And my phone died. And…" He trailed off as he waved the waiter over without so much as a hello.
Strike one.
"I'll have a beer," he said. Then he finally glanced at me. "You look… different from your photos."
Strike two.
I smiled tightly, resisting the urge to fling my stiletto at his perfectly arched eyebrow. "Different how?"
"Yeah," he grumbled vaguely, already thumbing his phone, "the light. Angles. Filters."
Strike three.
I sent Jenna a text from under the table: SOS. Wrong man. Wrong shoes. Send assistance or a forklift.
She responded promptly: New rule—if he makes fun of your profile picture before appetizers, RUN.
The problem was, I couldn't run. Not in these shoes. So I simply sat there, sipping wine, smiling graciously, and wondering why the universe hated me.
Because if this is dating at twenty-nine, I was in trouble big time.
Adrian asked me not one question when we waited for our food. Zero. He scrolled. He complained. He laughed at something on his phone, extending it out to me to look at a blurry meme I didn't want to look at.
When the waiter emerged with our plates, Adrian leaned back with a sigh.
"Alright, so what do you do?" he said, addressing the question like one would ask a mechanic about brake pads.
I impaled a piece of salmon. "I'm in marketing."
"Oh, like commercials? Ads? TikTok stuff?" He grinned. "I could've done it. I'm great at generating ideas. Once I pitched a brand of energy drink on a new slogan 'Fuel Your Hustle.' Never heard back, but it was genius."
I chewed on purpose. "Very genius."
When the dessert menus came, my shoes had waged an outright war against my feet. I limped to the bathroom, veteran-waist, and locked myself in a stall.
I then texted Jenna again: Is faking food poisoning too obvious?
She texted back: Yes. But do it anyway.
I looked into the mirror. Frizzy hair, melting makeup, face that screamed Why am I like this? I was twenty-nine years old, mid-cycle of a job that was sucking the life out of me, and hanging out with a guy who thought hashtags were hobbies.
That's when it hit me.
Not just the excruciating agony of the shoes, but the bigger picture: this wasn't one little mistake. This was a trend. A collection. A meticulously collected museum of poor choices, paid for only by me.
The Wrong Shoes. The Wrong Men.
When I returned to the table, I'd made up my mind.
Adrian," I said, sliding into my seat and pushing my credit card across the bill before he could get up, "thanks for tonight."
He looked confused. "We're not even done."
"Oh, I am."
I grinned, got up, and staggered heroically to the door. Every step was torture, but with every one of them, I felt stronger, lighter. Almost free.
And with that, I wrote my first rule:
Rule #1: No stilettos. No men who need to be alone.
The cool night air outside slapped me in the face like freedom amidst a cloud of exhaust fumes. I kicked off my stilettos on the sidewalk, eliciting curious looks from strangers passing by, and trudged down the street with them as trophies of questionable judgment.
My phone buzzed. Jenna, of course.
Status? Still alive?
I answered: Barefoot. Broke up with him before we were technically an item. May be wedding myself now.
Three dots foamed, then: Finally. Been waiting for you to join me on the dark side.
I smiled, hobbled to the subway entrance, and pondered my life. Pondered the endless merry-go-round of almost-relations, the two or three pairs of shoes I'd bought because they "felt right" even when they didn't, and how maybe possibly those were the same.
I sat cross-legged on my bed that night with a notebook. The shoes lounged unfilled on the floor, their pointed tips accusing me like evil little goblins. I skipped them and began writing at the top of the page:
The Rulebook.
Rule #1: No more stilettos. No more men who can eat alone.
Rule #2: Stop using "interesting" as a synonym for "good for me."
Rule #3: If it hurts when you begin, it'll hurt more when you end.
As I put the top on my pen, something within me was calmer. As though maybe I had a chance of sorts. As though maybe, for the first time in history, I wasn't going to blunder into another disaster.
The universe, naturally, was already mocking me.
Because within less than twenty-four hours, I would run into the man who would violate every one of the rules I'd just set down.