I went on a date with a guy my friend set me up with. He showed up with flowers (not a grocery store bunch, actual roses). Dinner was perfect. He was charming, opened doors, and pulled out my chair. When the check came, I reached for my wallet. Big mistake. “Absolutely not,” he said, sliding his card down. “A man pays on the first date.” I walked away thinking it was one of the best first dates ever.
That was until the next morning, when I saw that he’d sent me a Venmo request—for half the dinner bill.
At first, I thought it had to be a joke. The message attached was: “You said thank you, but thank-you doesn’t pay the tip.”
I just stared at the screen. I even laughed, thinking maybe he was being cheeky. But then I noticed the amount. $67.48. Exactly half. Not a symbolic dollar or something cute. Not even rounded down. He wanted me to literally split the bill after insisting he pay.
I screenshotted it and sent it to my friend Faria, who’d set us up. She replied, “Wait, WHAT? That makes no sense. I thought he was all about being old-school romantic?”
“Yeah,” I replied. “Apparently only until the bill comes and he rethinks his life.”
I ignored the request. Two hours later, he messaged me:
“Hey, just making sure you saw my Venmo. I believe in fairness in relationships, hope you understand.”
Okay. Fairness? He refused to let me pay the night before. And now he’s trying to backcharge me like I’m some Uber passenger?
Still, I kept calm. I wrote back:
“I thought you didn’t believe in splitting first dates. You were pretty clear about that.”
He replied instantly:
“I don’t. But I also don’t believe in being taken advantage of. You ordered the truffle pasta, btw.”
That was the moment my jaw actually dropped. The truffle pasta? Are we serious right now?
I could’ve roasted him. I could’ve gone full scorched earth. But something told me to step back.
Instead, I texted Faria again and said, “Your boy just invoiced me for truffle pasta.”
She called me laughing so hard she couldn’t breathe. “I’m so sorry. I swear I thought he was normal. I had no idea he was like this.”
“I mean…he brought roses,” I said. “Roses!”
Faria sighed. “He’s one of those guys who studies dating like it’s a strategy game. Like, says all the right things, but it’s transactional underneath. Honestly, I thought he’d grown out of that.”
I deleted the Venmo request. Then I blocked him.
I wish that was the end of it.
The next day, he tagged me in a public Instagram story—PUBLIC—that said:
“Don’t let good looks fool you. Some women are in it just for the free ride. #trufflehunter #learnedthehardway”
With a GIF of a gold digger using a shovel.
I hadn’t even responded yet, and he was out here smearing me online.
Now I was pissed. I screenshotted the story and sent it to Faria again. “Okay, I’m gonna drag him. Unless you want to step in?”
She said, “Give me a sec.”
Ten minutes later, she texted back:
“Update: I just messaged his sister. She says this is not the first time he’s done this. Apparently, he keeps a spreadsheet of his dates, what he spends, and if it’s ‘worth it.’”
A spreadsheet.
I was stunned into silence.
“He calls it his ‘ROI of romance,’” she added. “She says he literally has columns for time spent, how much he paid, and ‘emotional availability.’”
“That’s sick,” I replied.
“Yeah. She offered to talk to him. But I kind of want to make popcorn instead.”
I should’ve walked away. Should’ve let it die there.
But no. That man dragged me online. I had to clear my name.
So I posted a story with no names, no tags, just a calm, dry recap:
“Went on a date. He insisted on paying. Next day, he Venmo’d me for half the check and tagged me in a story accusing me of being a gold digger. Over truffle pasta. Do better.”
It blew up.
People started sharing it. DMs flooded in—some laughing, some furious on my behalf. A few even sent me screenshots of their own run-ins with him.
One woman, Priya, messaged, “Wait. Is this guy named Milan? Went to Vassar? Drives a black Audi?”
“YES,” I replied.
She sent a crying emoji. Then:
“He did the exact same thing to me. Ordered an expensive bottle of wine, insisted on paying, then later sent me a Google Doc with a breakdown of ‘what I owed’—including the Uber to the restaurant.”
I couldn’t believe this was a pattern.
Within 24 hours, I’d heard from five other women. Same story, same guy.
The final straw came when one girl—Talia—sent me a screenshot of an email he’d sent her last year, titled: “A Recalibration of Expectations.”
I nearly fell out of my chair.
Who writes that to someone after a date??
Talia had gone on three dates with him. He’d ghosted her, then sent her that email claiming he was “reconsidering the cost-benefit ratio” of continuing to see her.
It read like a business memo.
Now I was officially done being quiet.
With permission, I compiled anonymous snippets from all six women into a TikTok (no names, no faces). Just a voiceover reading out the messages while I zoomed in on receipts:
– “He sent me a Venmo for exactly $38.22.”
– “He added a tip calculation based on how much wine I drank.”
– “He asked for reimbursement for a Lyft he didn’t even take.”
The caption:
When a man turns dating into a spreadsheet, RUN.
I woke up the next day to 75,000 views. Then it hit 250k. Comments blew up.
People were furious. Others joked he should just date his Excel sheet. A few even guessed who he was.
But the real twist?
His boss saw the video.
Someone who worked with him recognized the car and the voice from a podcast he’d guested on about “tech efficiency.” They forwarded the video to HR at his company.
That might sound harsh. But turns out, this guy had also been talking to female interns about his dating theories. On company time.
Two weeks later, I got a message from his sister again.
She wrote, “Hey… so he’s on ‘leave.’ Apparently the video caused some waves. I just wanted to say, I’m sorry. For real. I’ve tried to talk to him, but he doesn’t listen to women—not even me.”
I thanked her. I wasn’t trying to get him fired. I just wanted him to stop weaponizing kindness.
The flowers. The charm. The chair-pulling. All just tactics to build a fake sense of security. Then he’d flip it and shame you for accepting what he offered.
It was never about dinner. It was about control.
Funny enough, a couple of months after it all blew over, I got a message from one of the women he’d dated—Talia. She asked if I wanted to get coffee sometime. “Trauma bonding,” she joked.
We met up. Talked for two hours straight. Shared everything we’d gone through—not just with him, but other guys who made us feel like we were too much, too little, too expensive, too emotional.
It was oddly healing.
Now, a year later, we’re actually friends. A real, laugh-till-you-snort kind of friendship. She even helped me move apartments last month.
And I did end up going on a few more dates—slowly, carefully. One guy, Levan, was quiet, thoughtful. On our second date, I offered to split the bill. He didn’t make a big speech. Just smiled and said, “If you insist, we can take turns.”
No performance. No passive-aggressive texts. Just… a grown-up conversation.
We’ve been seeing each other for seven months now.
Here’s the thing I learned:
Real generosity doesn’t keep score.
If someone offers you kindness, then punishes you for accepting it, that’s not romance. That’s emotional manipulation in a button-down shirt.
Good love doesn’t come with an invoice.
So if you’re out here dating—don’t be afraid to take people at face value. But don’t ignore the receipts, either. Sometimes, they tell the real story.
If this resonated with you, like and share it with someone who needs a reminder: you are not “too much” for expecting decency. You’re just too real for people who treat love like a transaction.
