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 bill—plus tax and tip.

At first, I laughed, thinking it was a joke. Who pulls that after making such a show of being “traditional”? But the note attached said, “Just trying to be fair. Equality, right?” with a winking emoji. My stomach dropped.

I texted him, thinking maybe there was some misunderstanding. I didn’t want to assume the worst. I even said, “Hey, not sure if that was meant for me?”

He replied, “Yep. I just think modern dating should go both ways. Nothing personal :)”

Okay.

I didn’t know if I felt more insulted or embarrassed. I had told my best friend, Irina, all about the date. She was the one who introduced us. She was already picturing a double date with her and her fiancé.

When I told her about the Venmo request, she went totally silent for a second. Then she said, “Oh my god. No. He did not.”

“He did,” I said, still staring at the screen. “Eight hours after dropping me off.”

I wasn’t even upset about the money. It was just the bait-and-switch of it all. Like, don’t give the speech about how a man pays if you’re gonna invoice me after dessert.

Irina felt terrible. She said she’d known him through work—he was her company’s old marketing consultant—and he always seemed “old-school gentleman” to her. Clearly, something was off.

That should’ve been the end of it. But two days later, I got another Venmo request—from the same guy. This time for $4.75. His note said, “Gas money. You live kinda far 😅”

I blocked him after that.

I thought it was over, but then the reviews started.

Not on Yelp or Google. On me. Personally. On a Reddit thread I’d never heard of, but Irina’s fiancé stumbled across it when looking up the guy’s company.

There was a whole post. He didn’t use my name, but it was obvious. He described our date, exaggerated a few details (“she ordered the lobster,” which I didn’t), and ended the post with: “When women say they want chivalry, they really mean they want a free meal. Classic entitlement.”

It had over 300 comments.

People were debating the ethics of dating and paying and everything in between. A few even guessed where I worked—right. from. my. outfit. (I’d worn a jacket with my company’s logo embroidered small on the sleeve.)

I was mortified.

I told Irina everything. She was furious. “I vouched for this guy,” she said. “And he turned out to be a complete trash can in a collared shirt.”

Here’s where things get interesting.

A week later, Irina had lunch with one of her old colleagues—someone from the company that had hired him as a consultant. Irina kept things casual, just asked, “So how was working with Alain?”

The colleague paused and said, “He was good… until he started messaging two interns and sending weird voice notes after hours. HR got involved. You didn’t hear?”

No. We had not.

Apparently, Alain had left on “mutual terms” six months before. But that wasn’t public.

That little discovery lit a fire under Irina.

She told her boss everything. He happened to be very protective of Irina—plus, he had once met Alain at a fundraiser and didn’t like how he talked over the women on the panel.

Long story short, Alain’s reputation in their professional circles took a hit. Not because of our date—but because people started sharing stories. A pattern. Polished charm, passive-aggressive sexism, and strategic oversharing.

Somehow, karma was making its way through the cracks.

But I still felt gross about the whole thing. It wasn’t just that he’d tried to embarrass me online. It was the way he weaponized “fairness” to look like a victim.

And then, another twist.

Two months after the whole Venmo thing, I got a LinkedIn message from a woman named Lais. She said, “Hi, I hope this isn’t weird. I saw your name tagged in a reply on Reddit. Did you go on a date with Alain C. in May?”

My heart stopped.

She went on to say she’d dated him for two months last year. It started out amazing—lavish dates, sweet texts, long walks. Then came the lectures.

He’d scold her for not offering to pay for coffee. He’d say she was too “comfortable.” Once, when she bought herself new boots, he said, “Must be nice not having real financial pressure.”

She’d left after he accused her of using him for free Netflix.

We talked on the phone for nearly an hour. Lais was sharp, funny, and real. She’d seen the Reddit thread, read my comments, and wanted to say, “You’re not crazy. He does this. To multiple women.”

That phone call turned something in me.

I stopped feeling ashamed and started feeling angry. Not just at him, but at the culture that lets guys like him hide behind a veneer of fake feminism or “equality” while still playing power games.

I ended up writing a post about it on my private Instagram, just for friends and family. I didn’t name him. I didn’t need to. I just laid it out: the flowers, the chivalry, the Venmo charge, the Reddit post, the casual gaslighting. I said, “Sometimes it’s not about the $47.25. It’s about someone showing you exactly who they are, then trying to make you feel small for noticing.”

It blew up. Friends shared it. Strangers messaged me. And slowly, I realized something: we’ve all met an Alain. In dating, in work, even in family. People who do just enough “good” to confuse you, then flip the script when you call it out.

Then came the final twist.

About three months later, Irina forwarded me a wedding website.

Alain was getting married. To someone else entirely.

The part that made my jaw drop? The registry.

He had listed “Gas Cards” and “Streaming Subscriptions” as gift options. Like… are you serious? The man put Hulu Plus on his wedding wish list.

I clicked through her profile. His fiancée was stunning and seemed genuinely sweet. Her Instagram was full of nature hikes and homemade cinnamon rolls. It made me sad.

But I didn’t feel bitter.

Because I knew now—it was never about me. People like him don’t target one type. They just keep spinning their charm until someone gets caught in the net.

And sometimes, people don’t realize they’re being spun until it’s too late.

If there’s one thing I’ve learned from this, it’s that how someone acts when they think they’ve “won you over” tells you everything. Flowers and charm are easy. Respect, consistency, and humility? That’s the real deal.

Oh—and always check the note on a Venmo request. It might just expose someone’s whole personality in four words or less.

If you’ve ever had a date turn into a cautionary tale, share this. Let’s help each other dodge the charmers with calculators.

💬 Drop your story below. I swear, I’m reading every single one.