You've probably seen it on your FYP or scrolled past it on Twitter during a heated debate about dating ethics. The phrase make his pockets hurt has become a sort of digital war cry. It sounds aggressive. Maybe even a little mean-spirited if you take it at face value. But honestly, the internet rarely does "face value" well. What started as a cheeky way to describe dating for financial gain or seeking "retribution" through expensive dinners has morphed into a complex cultural touchpoint about power dynamics, the cost of living, and how we value companionship in 2026.
Money is awkward. We hate talking about it, yet we can't stop posting about it. When someone says they want to make his pockets hurt, they aren't always talking about literal bankruptcy. Usually, it’s a reaction to the "bare minimum" culture that’s been dominating the dating scene for the last few years.
Where the phrase actually came from
Let’s be real for a second. The idea of "bleeding someone dry" isn't new. It’s as old as time. However, the specific vernacular of making pockets hurt exploded within Black Twitter and TikTok subcultures before hitting the mainstream. It’s often associated with the "City Girls" energy—a movement sparked by the hip-hop duo City Girls, who champion women putting their own financial needs first.
It’s about leverage. In a world where the gender pay gap still persists and emotional labor often falls on one side of the fence, some people view financial "spoiling" as a way to level the playing field. It's a transactional mindset, sure. But it's a mindset born out of a very specific frustration with modern romance. You’ll hear it in songs by Latto or Cardi B, where the lyrics celebrate men spending lavishly. It’s less about the money itself and more about what the money represents: effort, sacrifice, and status.
The psychology of the "Pockets" trend
Why does this trigger people so much? Because it flips the traditional "provider" script on its head and turns it into a demand rather than a gift. When a creator posts a video showing off a $5,000 Bottega Veneta bag with the caption "made his pockets hurt," the comments section usually turns into a battlefield.
Psychologists often point to "Social Exchange Theory" here. Basically, we all subconsciously track what we put into a relationship versus what we get out. If a woman feels she is providing high-level emotional support, beauty maintenance (which costs a fortune in 2026), and time, she might feel that an expensive date or gift is the only way to balance the scales. It’s a messy way to look at love. Kinda cold, right? But for many, it's a survival mechanism in a dating market that feels increasingly low-effort.
💡 You might also like: Virgo Love Horoscope for Today and Tomorrow: Why You Need to Stop Fixing People
But there’s a flip side. Experts like Dr. Wendy Walsh, who specializes in the psychology of love, often discuss how transactional dating can lead to a "devaluation of the self." If the goal is solely to make his pockets hurt, the relationship becomes a series of invoices rather than a connection. You’re no longer a partner; you’re a line item in a budget.
The "Splitting the Bill" War
We can't talk about this without mentioning the 50/50 debate. This is where the phrase really gets its teeth. In 2024 and 2025, the internet nearly broke over the "Cheesecake Factory" video and the "Sprinkle Sprinkle" lady (Sheraseven). These creators pushed the idea that women should never pay for anything.
The logic? If he's not spending, he's not invested.
Many people using the phrase today are reacting against the "coffee date" meta. They’re tired of the $7 latte being the price of admission for their time. So, they go to the extreme. They want the steakhouse. They want the shopping spree. They want to see the bank account flinch. It’s a performative display of worth.
Misconceptions and the "Gold Digger" Trope
Is it just gold digging with a new name? Not exactly.
📖 Related: Lo que nadie te dice sobre la moda verano 2025 mujer y por qué tu armario va a cambiar por completo
The "gold digger" archetype is someone who seeks out a wealthy partner specifically for their money. Making his pockets hurt is often more about punishing a specific behavior or testing a guy's "generosity" regardless of his net worth. It’s often used as a defense mechanism after a breakup. "He wasted my time, so I'm gonna make his pockets hurt" is a common sentiment after a betrayal. It’s a form of digital-age alimony.
However, we have to acknowledge the toxicity. When the goal of a relationship is financial harm, nobody wins. Real wealth—both emotional and financial—is built through collaboration, not extraction.
The Economics of 2026 Dating
Inflation hasn't been kind to our social lives. A "cheap" night out in most major cities now clears $150 easily. When you factor in the "beauty tax"—hair, nails, makeup, the outfit—a woman might spend $300 just to show up to a date. When the guy wants to "split the bill" or keep it "casual," the resentment builds.
That’s the environment where this phrase thrives. It’s a pushback against the rising costs of existing while dating.
How to navigate the "Pockets Hurt" Era
If you're out there in the trenches of Tinder or Hinge, you’ve got to have a strategy. You don't have to be a victim of the trend, nor do you have to be the one trying to bankrupt your partner to feel valued.
👉 See also: Free Women Looking for Older Men: What Most People Get Wrong About Age-Gap Dating
Set the "Investment" Standard Early. You don't need a Birkin to show you have high standards. Clear communication about what you value—whether it's thoughtful planning or financial generosity—prevents the need for "revenge spending" later.
Understand the "Soft Life" Movement. A lot of the people saying make his pockets hurt are actually just trying to subscribe to the "Soft Life." This is a lifestyle choice prioritizing comfort and low stress. If your version of a soft life requires a partner with deep pockets, be honest about that up front. Ambiguity is where the drama starts.
Check the Intent. Are you asking for a gift because you love the item, or because you want to see if he’ll hurt for you? There's a massive difference. One is a love language; the other is a power play. Power plays usually end in ghosting or resentment.
Financial Transparency. In 2026, the most radical thing you can do is actually talk about your budget. It’s not "un-romantic" to know what someone can afford. It’s mature. The most successful couples aren't the ones trying to out-spend each other; they're the ones who have a shared vision of what their money should do.
The phrase will eventually die out. Slang always does. But the underlying tension between money and romance? That’s staying forever. Whether you’re trying to make his pockets hurt or you’re looking for a 50/50 partnership, just make sure you aren't losing your own sense of value in the process.
Actionable Steps for the Modern Dater
- Audit your "dating tax": Calculate what you actually spend to go on a first date. If the ROI (Return on Investment) isn't there, change your strategy. Don't use a date as a way to "get back" what you spent on your hair.
- Define your non-negotiables: Is it the dollar amount of the date that matters, or the effort? Often, a well-planned, unique experience feels more "expensive" than a lazy dinner at a pricey chain.
- Watch the red flags: If someone's entire personality is based on how much they can extract from others, they’re likely hiding a lack of substance. This goes for both sides.
- Prioritize financial literacy: Before worrying about someone else's pockets, ensure yours are deep. Financial independence is the ultimate leverage in any relationship. It means you're there because you want to be, not because you need to be.
Modern dating is a mess of mixed signals and viral trends. Don't let a TikTok caption dictate your relationship values. Know what you want, be clear about it, and remember that real luxury isn't just about what's in the wallet—it's about the quality of the person holding it.