Keisha tried me

I almost broke my own rule.

Sep 10, 2026

I promised myself I wouldn’t dine out in August.

Then I met Keisha.

Keisha had me ready to break all the rules.

We matched on a popular dating app, and I couldn’t believe my eyes. She was gorgeous, fashionable and, more importantly, polite and engaging from the jump. We exchanged a few messages, complimented each other and I did what any rational man who had sworn off restaurant spending would do.

I asked her out.

One of the prompts on her profile said the best way to ask her out was simple: plan the date and tell her what time to be ready. I could do that.

I told Keisha when and where. The destination was a swanky steakhouse — the same one where I met white Kristen four years ago. Apparently, I have a thing for expensive restaurants with complicated dating histories.

There was just one problem.

The steakhouse was booked for a private event that night.

I immediately told Keisha and, following her instructions, made a reservation at an Italian restaurant across the street.

That’s when I got my first sign that this date might not make it to the table.

“Good evening Darnell that sucks that we’re not able to find another steakhouse,” she wrote.

My first thought was: Who is we?

I kept that thought to myself.

“I hear you. It’ll be great regardless,” I replied.

Strike 1.

The next day, the day of our date, we exchanged cordial good-morning messages. Then Keisha asked:

“So where are we meeting this evening?”

I had already told her.

I sent the information again.

Strike 2.

Then came the knockout.

“Are there any other options to choose from?”

Strike 3.

At that point, I was done.

I had already made the reservation. I had already committed to the date. And I had done exactly what Keisha said she wanted: I planned it and gave her a time to be ready.

But after a financially turbulent five months, something else was happening. I was about to break a promise to myself for a complete stranger.

So I respectfully backed out.

I told Keisha we probably weren’t a good fit and that I would cancel the reservation. I also realized I didn’t need to add another expense to an already expensive year.

Most of my purchases go on a credit card so I can rack up airline points. A few essentials — my mortgage, gas, electricity and my $10-a-month gym membership — are paid separately. Tracking everything this way gives me a real-time picture of where my money goes, and every month I share the good, the bad and the occasionally embarrassing with you.

My credit card statement showed $4,852 in spending last month. That was just $23 more than I spent in August 2025.

That made August my fifth consecutive month with more than $4,000 in credit-card spending.

Professional services once again led the way, accounting for 47 percent of my spending.

But groceries told a more important story. I spent $771.83 on groceries in August, my highest total in some time.

I kept my word.

I bought groceries. I prepared food. I ate at home.

For the most part, anyway.

The $1.86 Dunkin’ charge tells on me. But I have no regrets about that one.

It was the first day of school, and I owed Parker a strawberry-frosted-sprinkle donut.

Parker and her donut on the first day of seventh grade on Aug. 19, 2026.

She started seventh grade last month. She’s only a few months away from becoming a teenager, which means the clock is ticking on the number of years I have left before Dad’s annual back-to-school donut tradition becomes deeply uncool.

For now, though, she still wants her donut.

And some promises are worth breaking.

I probably would have spent more than $200 on that steakhouse dinner with Keisha. I may or may not have seen her again.

Instead, the next day I spent $160 on groceries.

I ate at home for the rest of the month.

That $1.86 donut bought me something the $200 dinner couldn’t: another memory with my daughter.

That’s the kind of spending I can live with.