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.

I stared at my phone for a good two minutes, convinced it was a joke. $67.42. Even the cents were exact. He’d tagged it with a little pizza emoji and a winky face. Not “Hey, had a great time!” or “Let’s do it again soon.” Just the number and that damn emoji.

My gut reaction was to decline and block him. But curiosity got the better of me, and I messaged him instead.

“Hey…is this a mistake?”

Nope. He replied instantly. “Not at all. I just think it’s fair. You ate too, right?”

I didn’t know whether to laugh or be offended. This man had insisted—insisted—on paying, made a whole show of it, and now this?

I texted my friend who set us up. Saira, my roommate from college, the queen of “you need to get out more” pep talks. She responded with a sigh so loud I could hear it through the text.

“Oh my God. Again?”

That got my attention. “Again??”

Apparently, I wasn’t the first woman he’d pulled this on. Saira told me he liked “theatrics”—playing Mr. Old-Fashioned at dinner, then quietly charging women afterward. She thought maybe it was his weird way of filtering out “materialistic” women, which made no sense considering he initiated the date and chose the place.

I declined the Venmo. Didn’t say a word. Just moved on.

But that was the start.

The thing about a bad first date is, usually, it ends there. You cringe, maybe you laugh about it later, and you move on. But not with Arman.

A week later, I’m at this pop-up food market with Saira and our friend Dinah, just trying to enjoy a Saturday. Guess who’s there, leaning against a taco stand, looking smug?

“Hey,” he said, like we were buddies.

I tried to be polite, but something in me tightened. He acted like nothing had happened. Even asked if I still had his number.

“I do,” I said, “but I’m not sure why I would use it.”

That should’ve been the end. But Arman wasn’t the type to take a hint.

He DM’d me later that night. A full paragraph explaining how “modern dating has lost its logic” and how “splitting the bill is the only fair method.” He even attached a podcast episode link titled The Economics of Courtship.

I left him on read.

You’d think that’d be enough to discourage a guy. But Arman had the persistence of a Wi-Fi signal in a basement—weak, annoying, but always kind of there.

He started commenting under my Instagram posts. Not creepy stuff, just things like “🔥” or “Queen 👑” or “Where’s this taken?”

Always juuuust normal enough not to warrant a block. But annoying enough to feel like a gnat buzzing around my face.

It was Dinah who finally said, “You need to shut this down. Not passive-aggressively. Actually shut it down.”

So I did.

I sent him a message, clear as day:

“Arman, I’m not interested. I didn’t appreciate the Venmo request. Please don’t contact me anymore.”

He replied with a single word: “Understood.”

Great, I thought. Peace at last.

Two months passed. Life went on. I even started dating someone new—Jorge, a teacher with the patience of a monk and the best laugh I’d ever heard. No drama, no games. Just easy.

Then one night, I get a text from a number I don’t recognize.

“Hey, this is Nida. I’m Arman’s sister. Can we talk?”

I stared at it for a minute. What now?

We spoke the next day. Nida was kind, articulate, and—to my surprise—not calling to defend her brother.

“Listen,” she said. “I found your number going through his old texts. He’s in a bit of trouble. And I think some of it…well, it circles back to how he’s been treating women.”

That caught my attention.

Apparently, Arman had been playing this Venmo game with more than a few women. And not just one date—he’d gone on second and third dates, always insisting he pay, then later sending retroactive charges. Some of the women paid to avoid conflict. A few pushed back. One posted screenshots on TikTok.

It spiraled.

His name got around. A small account did a “Tales of Terrible Tinder Dates” series, and Arman was episode #4: The Guy Who Sends Invoices.

And then his employer found it. A small but reputable marketing firm. He was let go within the week—not because of the TikToks directly, but because of “unprofessional conduct” and “disrepute concerns.”

His sister wasn’t calling to guilt me. In fact, she apologized.

“I know this might sound weird,” she said, “but thank you. You called him out early. Most women didn’t bother. I think it forced him to finally see the pattern.”

Apparently, he was now in therapy. Trying to work through what Nida delicately referred to as “entitlement issues.”

It wasn’t the ending I expected.

I didn’t feel vindicated, exactly. Just…sad, in a way. Arman wasn’t evil. He was insecure, probably deeply lonely, and trying to game a system he didn’t understand.

I never spoke to him again.

But about six months later, I got a letter. A real one. Mailed to my apartment.

The handwriting was neat, slanted, like someone trying to write carefully.

It was from Arman.

He wrote:

“I don’t expect forgiveness. But I do owe you an apology. I thought I was being clever—dodging the ‘free meal’ trap or whatever nonsense I convinced myself was real. But I was just being petty. Small. And you didn’t deserve that. None of them did. I’ve got a lot to unlearn. I’m sorry I learned it through hurting people like you.”

There was no return address. Just a name and a simple message.

I sat with it for a long while. Not sure how I felt.

But here’s what I’ve learned: the real red flags aren’t always loud. Sometimes, they show up wrapped in roses and good manners. They pull out chairs, say the “right” things, then quietly bill you for dinner the next day.

Charm without integrity is just manipulation in cologne.

I’m still with Jorge. He doesn’t always open doors, but he listens. He asks questions. And not once has he ever made me feel like kindness was a transaction.

If you’re reading this and you’re dating—don’t ignore the little gut punches. Trust your instincts. And if someone shows you who they are with a Venmo request…believe them.

Like, share, and tag someone who needs to hear this. You never know who might be on a date with an Arman right now.