A dating disaster
The story of white Kristen.
I met white Kristen on a dating app. It’s how I’ve connected with probably 90% of the women I’ve dated since my divorce.
Technology makes everything easier.
But anyone who has ventured into the virtual dating streets knows that convenience hasn’t made dating itself any better. There’s much more to online dating than simply swiping left or right on an attractive photo.
First, you must make sure people are who they say they are. Moving from messaging to a meeting can be messy. Anyone can woo you with words and fool you with filters. That’s assuming they show up at all. I’ve also run into my share of flakes.
I used to pay a monthly fee for said frustrations.
I told you in March of 2023 that dating was among my money pitfalls. Following my divorce, dating was one of the few activities that felt good.
Looking back, I can understand why. I was married at 27, after more than three years of commitment to Parker’s mother. Until then, I was all about my career. And after Parker’s birth, my life became all about her.
For me, dating wasn’t just another distraction. And although I enjoyed certain aspects of the dating scene, I also know now that I was in it for more than fun. I grew from each experience no matter the duration. I got to know many different types of women. I learned a lot about myself as well.
A few women that I’ve met along my journey remain a part of the Money Talks family. You know who you are. We appreciate your continued support.
For all of the frustrations that come with dating, I never dreaded it like so many do. Still, it took me hundreds of interactions just to land a handful of quality connections over nearly a decade. I also grew tired of the outsized expectations on men to shoulder the entire burden early on, from planning dates to preparing for them to, of course, paying. Shout-out to the women who always chipped in however they could.
The older Parker got, the more I knew she was the only girl worthy of my money. Whenever I went out for dinner or drinks with a woman I didn’t know, I left thinking about the money I could have funneled to Parker.
My dating days began dying a slow death.
And then white Kristen came along and smothered my remaining interest in these streets. It’s been two years since that unforgettable day.
An unexpected entrant into my dating life in part because she was white, Kristen managed to ace the preliminary stage. In messages via the app, she was engaging, thoughtful and witty. She got bonus points for having pictures that reflected a real person.
We exchanged numbers and met on August 2, 2022, a Tuesday night. My plan was to have one drink. My drinking habits had changed, and I was fresh off the $3,700 car repair bill that spawned Money Talks. The last thing I was interested in was footing the bar bill for another complete stranger.
But one drink became two, and after 45 minutes I didn’t mind picking up the tab. Our in-person conversation surpassed our comfortable back-and-forth via messages. We shared a lovely goodnight kiss, with the kind of chemistry that you can tell could lead somewhere.
Sure enough, we connected for a second date 3 1/2 weeks later.
This time, all the financial restraint I had reserved for the first meeting was an afterthought. I recommended Sunday brunch at a wannabe swanky restaurant and bar in a hoity-toity Chicago neighborhood. That was my first mistake.
Back then, though, I still possessed an irrational love for pizza. My suggested establishment garnered excellent reviews for its pizza, and it offered bottomless mimosas to boot. I was sold, even after doing the math for the projected bill.
I arrived first, just before 11:30 a.m.
“Sitting at a table along the front windows,” I texted her. “Can’t miss me.”
For the next 2 1/2 hours, we had a grand time. The pizza was overrated and overpriced. Refills on the mimosas were slow and bordered on being a malicious rip-off. But we talked, laughed and connected in ways neither of us expected. She even offered to pay, which I respectfully declined.
We enjoyed our time together so much, we didn’t want it to end. We committed to continuing our date at the lake.
Before we left, I went to the men’s room one last time. My bladder has never been welcoming to alcohol. Somehow our server, who had been slow all day, returned the bill with my credit card faster than anything else she had done. By the time I got back to the table, expecting the check to come, the bill had already been paid.
My credit card beat me to the table. It sat face up in a room full of people I didn’t know.
“I hate it when they do that,” I murmured to my date.
The server didn’t know the nature of our relationship. She shouldn’t have returned my card to the table without me present. My mild frustration was aimed solely at the server but spoken only to my date.
That’s when she told me, like it was no big deal.
“We can go,” she said. “I left the tip.”
Kristen left the tip on my credit card.
I couldn’t believe it. I thought I was being pranked.
Politely pointing out my issue, however, promptly backfired. The woman grew defensive and distant. In a matter of seconds, she withdrew.
Instead of the lake, she said she was going to take off. I didn’t try to stop her. We gave each other a half-hearted hug and went our separate ways.
At 2:06 p.m., I sent her a text from my car. Again, I extended her the benefit of the doubt.
“Hey,” I wrote. “Hate that whatever happened just happened. Not sure if it was a miscommunication or what. If you left your own cash and I didn’t understand, cool. Excuse me. If you paid the tip using my card, that wasn’t cool and that was my issue. Either way, it was nice meeting you. I had a good time today. Enjoy the rest of your day.”
You would think that would have been a Band-Aid, if nothing else.
Wrong.
The woman simply couldn’t see my side.
“I offered to pay so I clearly was not interested in spending your money,” she texted, “and I left the standard 20% tip that was already in the machine so I didn’t go crazy with your money.”
Y’all already know how I feel about tipping. But that’s beside the point for once. In her response, Kristen basically labeled me an angry Black man.
I explained to her that I never would have taken such liberties if the roles were reversed. Never would I even think to do anything with someone else’s money without their permission.
Kristen’s inability to grasp this concept made me think our disconnect was cultural.
I’ve always been an equal opportunity dater. But I’ve only seriously dated two white women. The second woman is one I met not on a dating site but on a plane.
That relationship crashed and burned here in Chicago during a meetup before I moved here. The woman had a big-time career and made significantly more money than me, which was as difficult of an adjustment as anything cultural. But when an argument that night escalated into the woman callously ordering me to “get out of my room,” I took her words to heart. It was her room. She paid for it. She tried apologizing and asked me to stay, but it was too late.
The optics of a Black man in a hotel room with an angry white woman on the north side of Chicago wouldn’t have been good for me. And so in the middle of the night, I packed my things and set out for the airport. We never saw each other again.
My first relationship outside of my race was a loving one I stumbled upon shortly after my separation. We did meet online. She wrote on her profile that she had a big heart and was very caring. And for five years, she proved it every day to me. It still is one of the best relationships I’ve ever experienced. She taught me how to love, and she’ll always have a piece of my heart.
But Chicago’s long history of segregation, and its continuing effects, played a large role in limiting my online matches mostly to Black women. Do not misunderstand that as a complaint. It’s simply a fact from my lived experiences.
So such a speedy breakdown in communication with the rare woman I’ve dated outside my race led to enormous confusion. Because no woman had ever left a tip using my credit card. I don’t remember my ex-wife even going there in the five years we were married.
From that day forth, she became white Kristen — although we never spoke again.
I paid $126.05 for our date that day. That included the $20 tip white Kristen left with my money.
She made things worse at 3:08 p.m., one hour after I sent my text from the car. Unsolicited, she attempted to reimburse me $20 for the tip.
Three minutes later, I sent her $20 back.
“Thank you,” I texted. “But it’s not about the money.”
White Kristen smothered my interests in these streets.
But it was that encounter that spurred me to stop swiping and start loving myself.
