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, 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 mistake. Maybe he accidentally sent it to the wrong person? But no, there it was: my name, the exact amount for half of our meal, and a little note that read: “Fair is fair.”

My stomach twisted. This was the same guy who had confidently declared that “a man pays on the first date.” I sat there, staring at my phone, debating how to respond. Maybe it was some kind of test? Maybe he wanted to see if I’d push back? Maybe he was just that kind of person who said one thing but did another?

I texted my friend—the one who set us up. “Hey, did you know your boy is out here charging for dates?” I attached a screenshot of the request.

She responded with a laughing emoji. “No way. That is so weird! He seemed like such a gentleman. Want me to ask him about it?”

I hesitated. A part of me wanted to ignore it, block him, and move on. But another part—the part that hates unanswered questions—needed to know. “Sure,” I replied. “Ask him.”

An hour later, she texted back: “He said he always does this. He pays upfront because it’s ‘tradition,’ but he believes in ‘modern equality’ after the fact. He assumed you’d be cool with it. Said he’s had issues with women using him for free meals.”

Oh.

That was…a lot.

I wasn’t mad that he wanted to split the bill—plenty of people prefer that. But why make such a big deal about paying in the moment if he was just going to invoice me later? Why not just say, “Hey, I prefer to split things evenly, hope that’s cool” upfront?

I sighed and messaged him directly. “Hey, I saw your request. I’m a little confused because you said you always pay on the first date, and I didn’t expect this. Can we talk about it?”

He replied within minutes. “Of course! Didn’t mean to surprise you. I always pay upfront because I think it’s classy, but I also think fairness matters. I hope that makes sense?”

I thought about it. Technically, I got a free dinner—until I didn’t. Maybe he had been burned before. Maybe he was trying to protect himself. Maybe he just had a weird system. Either way, I knew one thing:

I didn’t like it.

I declined the request and sent him a message: “Hey, I appreciate the date, but I think we have different expectations when it comes to this kind of thing. I don’t mind splitting, but I like honesty upfront. No hard feelings. Wishing you the best!”

He left me on read.

A week later, my friend told me he was ranting about me in a group chat. “Another one trying to get free dinners!” he wrote. “I’m done being a meal ticket.”

And that’s when it clicked.

This wasn’t about fairness or modern equality. This was about him keeping score.

I could respect someone who wanted to split things evenly. But I couldn’t respect someone who pretended to be a gentleman just to turn around and nickel-and-dime me later. If he’d been honest from the start, I might’ve even offered to pay for my half before the date began. But this? This was about control.

So, to anyone reading this:

People will show you who they are. Believe them.

And if someone acts like they’re doing you a favor just to turn around and make you “pay” for it later—whether it’s money, time, or energy—run. That’s not kindness. That’s a transaction.

Ever had a weird first date experience like this? Let’s hear it in the comments! Don’t forget to share if you’ve ever dealt with a walking red flag. 😉