Why He’s Making You Pay on a Date

Why He’s Making You Pay on a Date

We’ve accepted in this post-pandemic world that Dutch is the new normal—but what if he’s making you pay? Sis. Let’s talk. This is why he’s making you pay on a date.

Let’s back it up: Dating post 35 is a whole different kettle of catfish. You’ve healed (mostly), done the work, got the cute accessories, moisturised your trauma—and now some man is looking at you across the table like you should pick up the bill. Not split it. Not take turns. But you, Miss Independent, should cover the whole damn date like you’re his fairy godmother with an Amex.

So before you start wondering if this is modern love or modern madness, let’s unpack some reasons why he might be expecting you to reach for your purse.

1. He’s Testing You—Because Gold Digging Myths Won’t Die

Listen, we’ve all heard it: “Women just want a man for his money.” Even in 2025, this tired narrative is still on life support in WhatsApp groups and podcast rants from men who think asking a woman what she brings to the table is a deep philosophical inquiry.

So, he’s testing you. To see if you’re “not like the others.” To prove to himself that you’re not using him for a free dinner at Gaucho when all you really wanted was some decent conversation and a cocktail with an orange peel in it.

It’s a trap. A vibe check with no reward. And if you pass it, all he knows is that you’ll pay again. So, the question is—why does he need reassurance when you showed up with vibes, beauty and baby hair that stayed laid? Sounds like he’s the one who’s unsure what he brings to the table.

2. He’s Seriously Broke (But Still Hungry)

Let’s call it: some men are just dating for food. Yes, sis. Fine dining finessers. Hinge hustlers. They’ve figured out that if they act like a good listener, ask you how your day was and nod at your astrology references, they might just get an espresso martini and a ribeye out of it.

He’s not broke because of bad luck—he’s broke because he has no plan. And while there’s no shame in financial struggle, there is shame in dragging someone else into your lack without being honest.

He might not even be trying to get to know you. He just wanted to eat something that wasn’t microwaved. And if he fancies himself charming, he might think you won’t notice the pattern of him never offering to pay. Even though his debit card hasn’t been seen since the pandemic.

3. He’s Overstretched—Kids, Alimony or Cocaine

Let’s not sugar-coat it: adulting is expensive. He might not be broke, but he might be financially congested. That child support payment hits different when the weekend comes. Alimony is due. Or maybe he’s got a little habit he hasn’t disclosed yet—something that smells like powder and poor choices.

This man is overstretched. And guess what? You’re the flex in his financial plan. You look like you’ve got it together. And Black women, in particular, are often assumed to be strong, resilient and rich enough to handle it.

Nah. We’re not doing that in 2025. If his wallet is whispering while his mouth is making dinner reservations, he’s misaligned. It’s not your job to sponsor someone else’s budgetary illusions. Especially not in your grown era.

4. He’s Married—or Financially Entangled

Let’s get messy. Sometimes he’s not single, sis. He’s married. Or in a situationship with a joint bank account and a suspicious partner who checks Monzo statements like it’s a crime scene.

He can’t pay because he can’t leave a trace. There can be no digital breadcrumbs. No receipts. No “Just Eat” notifications from a postcode that isn’t his. You’re not being courted—you’re being covered up.

If the man is never paying and always cash-only with vibes of a burner phone and vague plans, be vigilant. He might be hiding more than his PIN.