No More Broke Dating for This 40-Year-Old Lady — Bye Bye Drizzlers

Listen, if you haven’t caught up with how dating works these days, let me help you out.

Dating isn’t what it used to be — and as a 40-year-old single mom who’s not looking for commitments, just good company and good energy, I’ve seen it all.

Here’s the truth: if a man’s trying to get laid, he better come with some sprinkle sprinkle or at least a little drizzle drizzle. But lately? These guys aren’t even bringing mist.

And honestly, I get it. Inflation’s sky high, the cost of living is ridiculous, and most people can barely save a dime. I’m not mad at men for watching their wallets — I’m doing the same thing.

I’m working hard now so I can retire at 50, so I’m not about to throw money around recklessly either. But what blows my mind is the expectation that they can show up broke and get laid.

Like… how are you broke and bold at the same time?

In the last five months, I’ve gone on dates with three different men — ages 45, 48, and 52. All of them older, all of them should’ve known better, but clearly age doesn’t guarantee emotional maturity.

Two of them were clock-in-clock-out 9-to-5ers. Respectable jobs, sure — but the entitlement? Out of pocket.

The third? A single dad who just launched his AI company and lives alone. Sounds promising, right?

Until he started acting like I should feel lucky just to breathe the same air as his “visionary genius.”

Let me tell you — each one came with a hefty sense of ego, demands that made zero sense, and the kind of entitlement that makes you tilt your head and go, “Wait… are you serious right now?”

One expected me to cook for him on the third date… after he took me to a chain restaurant and split the bill. Another gave me a speech about “traditional women” while asking me to drive an hour to his place — on a weekday — because he was too weak to drive.

The last one? Oh, he was the best of the worst. He spent half our date talking about his start-up, the other half explaining how “women like me” should be more supportive of men like him.

Meanwhile, he ordered the cheapest thing on the menu and forgot to tip.

Casual dating when you’re perpetually broke? Whew — it’s honestly an art form. You gotta get real creative.

Most fun stuff costs money, and like it or not, there’s always that pressure to show up and impress, even when your wallet is side-eyeing you.

Now, I’m not expecting a man to drop a fortune on a dinner date. I’m all for skipping overpriced steakhouses and opting for something a little more budget-friendly.

But there’s a huge difference between being financially smart and straight-up tacky. Asking your date for gas money? Yeah, no. That’s not frugal — that’s just foul.

You gotta find that sweet spot: being mindful of your money without making it painfully obvious. Like opting for free museum nights, quirky food trucks, or even a groupon adventure — can get you through those early dates without sacrificing fun.

Once you move past the small talk and into that “let’s actually get to know each other” phase? That’s where things get tricky.

Because at that point, it’s not just about being creative with your plans — it’s about showing effort, thoughtfulness, and maturity. And if a man can’t even manage that?

Then honestly, he’s not dating — he’s freeloading.

The reality really sank in after reflecting on my run-ins with these men. One after the other, it became crystal clear: most of them weren’t just emotionally unavailable — they were financially stuck.

And being in that kind of place makes it almost impossible to build anything serious. I mean, how do you even think about nurturing a real connection when you’re barely holding yourself together?

Let’s be honest — juggling two people’s emotional needs is heavy enough. Now add financial instability to the mix? It’s a recipe for resentment. I’ve been there.

In a past relationship, I lent money — emergency dental work, a few hundred bucks — to the man I was with at the time. It didn’t take long for that “help” to become a source of tension.

That small gesture turned into a loud, ugly argument, and it made me realize something: if a couple can go into a screaming match over $300, what’s going to happen when real-life expenses hit — property, cars, childcare, medical bills?

It’s not just about the money itself — it’s about security, stability, and shared responsibility. And honestly, I’ve got a child, a future I’m funding, and a retirement plan I’m grinding for.

I can’t afford to gamble all that on someone who can’t even afford to date.

That’s why I date casually, stay non-committal, and keep my peace (and pockets) intact. Love is beautiful, sure — but not at the expense of my goals.

Look, I know some idealists love to say that money shouldn’t matter when it comes to love. That it’s shallow to factor in income when choosing a partner.

But let’s be real: that’s not always practical.

In fact, it’s naïve.

There’s no bigger disaster I can imagine than two grown adults, both financially reckless, stuck in a relationship while drowning in bad credit, late rent notices, and zero backup plans.

How do you build anything stable when neither person has a solid foundation?

You can’t pour from an empty cup — and you definitely can’t build a life when both of you are constantly patching financial leaks.

Even when I was in my late twenties, the phase you think about buying house — I knew that combining my shaky financial past with someone else’s was already risky.

Trying to merge my journey with someone who was doing worse felt unfair — to both of us. And on the flip side, if his financial situation was better than mine, I’d feel the pressure of having to play catch-up just to feel like I belonged in the picture.

Now that I’m 40, that awareness has only sharpened. I don’t expect anyone to be rich, but I do expect them to be responsible. I’ve worked too hard — and been through too much — to tie myself to someone who thinks “we’ll figure it out” is a financial strategy.

I’m laser-focused on retiring at 50. Every dollar I earn is working for my future. So if I’m going to entertain someone, they need to bring more than just opinions, ego, and empty promises to the table.

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This post was previously published on medium.com.

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