So I went on this date...

Hey Uncle Gary,

So I went on this date. It was fun, he picked the spot, we had great convo, dinner was amazing. Afterward, we played pool at a bar around the corner, and he walked me back to my apartment. I kissed him goodnight. It felt sweet, like maybe the start of something. I was hoping I’d hear from him the next day… maybe a “had a great time, let’s do it again.”

Instead? Boom. A Venmo request. Half the bill.

I was honestly shocked. I always thought if a guy asks you out, he pays. Isn’t that just basic manners? Or am I being totally old-school? I live in the big city, dating’s already chaotic, and now I’m splitting the check like it’s a networking lunch? Help me out, am I wrong for expecting him to cover it?

Signed, Venmo Queen

Dear Venmo Queen,

Oh girl. You gave him a kiss and he gave you an invoice? That’s not a date, that’s a dinner receipt with a side of pool.

Let’s start here: you’re not wrong for feeling thrown. There’s a rhythm to dating, and while the “who pays” debate has evolved, the first date still carries a kind of social choreography. If he picked the spot, initiated the plan, and walked you home, it’s fair to expect he’d pick up the tab, or at least not turn the next morning into a transaction.

Now, does that make you old-school? Maybe. But old-school isn’t the same as outdated. It’s about intention. You weren’t expecting champagne and caviar; you were hoping for connection. And instead of a follow-up text, you got a bill. That’s what stings, not the money, but the message.

Here’s the bigger truth: dating in the city is chaotic. Everyone’s juggling apps, expectations, and emotional bandwidth. But manners still matter. Generosity still matters. And if someone’s idea of romance includes a Venmo request before breakfast, you’re allowed to say, “No thanks.”

You’re not wrong for wanting a little grace. You’re not wrong for hoping a sweet night might lead to something more. And you’re definitely not wrong for expecting a date to feel like a date, not a Dutch treat with a digital receipt.

Keep your crown, Queen. And next time, maybe ask: “Are you looking for connection, or just someone to split the bill?” But to keep this a clean date. Pay & Block.

Uncle Gary