She messaged me first on Seeking.
I’d bought a one-month subscription and figured I’d give it a whirl. Most of the women reaching out seemed like glorified hookers, but her message was different. She referenced the rooftop bar exploration I’d mentioned in my profile and suggested getting drinks.
She’d actually read the damn thing.
Promising.
Her profile wasn’t shy about describing her as “curvy.” The pictures were alright, but I wasn’t exactly rolling in it myself.
I’d been doing plenty of approaching lately, usually drunk, without converting much of it into actual dates. My confidence needed some maintenance.
So I figured I’d go on a date with training wheels.
We settled on La Palma Azul, a casual Mexican joint.
The First Inspection
I walked in and spotted her.
Short and stout like a little teapot.
But considerably better-looking than her pictures.
Good start.
She was 75% Dominican, 25% white, with surprisingly light eyes that immediately stood out.
Definitely an upgrade from The Slumpbuster.
She lived on the east side of town but had grown up in a small town in New York. She’d gone to film school and was now “pivoting” toward law.
Film school to law school.
I could already see why Seeking had entered the equation.
We started with the Summer Solstice, a mezcal cocktail. After the first round, I suggested moving to Henry’s, but she wanted another drink first.
Fine.
Round two was the Pineapple Wave. More mezcal.
Then she started craving fries.
Next stop: Grease Point.
On the walk over, I took her hand. She held it and began slowly caressing it with her thumb.
Signal received.
At Grease Point, I tried getting her to come back to my place. She mentioned she had to be at her bartending job at 8:30 the next morning.
I didn’t push further.
She was still down for another drink though.
So much for the early night.
We headed to Henry’s.
The Sugar Baby Résumé
This is where I got more of her Seeking history.
She told me the sugar baby scene had been huge in New York and that NYU had a reputation as the sugar baby school.
Her previous sugar daddy was apparently a right-wing white guy in his fifties or sixties. His gun collection eventually scared her off.
She said she liked me because I was younger.
Years of strip clubs made the flattery bounce off my chest.
Somewhere in the story, she also revealed that the man had weirdly shaved his entire body, suggesting their arrangement had progressed considerably beyond discussing firearms.
Then came another piece of intelligence.
She was bisexual.
She also had a six-foot Black female coworker with big tits whom she occasionally booty-called.
Nice.
I liked where this field report was going.
Security Breach
After Henry’s, I suggested one final stop: my coworking space.
Open 24/7.
The building was mostly empty, so we slipped into one of the quieter areas and started making out.
Things were progressing smoothly until she suddenly pulled back and pointed behind me.
Someone had walked in.
Operational security compromised.
Time to bounce.
By then, she was enthusiastic about seeing me again. We talked about meeting at the pool Saturday and sipping on THC margaritas.
Promising.
The Transaction
I walked her back to her car.
Right before getting in, she looked at me and half-joked:
“Wanna tip me for gas?”
There it was.
I almost expected her to pull out an iPad with the usual options.
15%. 20%. 25%.
For most of the night, this had operated almost exactly like a regular date.
Drinks. Fries. Hand-holding. Stories. Making out. Plans for Saturday.
Then, right before she drove off, Seeking reentered the conversation.
Not with a contract.
Just a request for gas money.
I told her maybe Saturday.
She got in her car.
I walked away.
I’d gone looking for a date with training wheels.
Apparently the training wheels had a tip jar.
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