Yes, You Should Always Pay for a Woman on a Date

And no, she doesn't owe you a fake wallet grab

April 15, 2022 7:15 am
A man holding out a credit card as he pays for a dinner date with a woman
Wallets out, boys.
Ariel Skelley

The last time I pretended to offer to pay for a date was four years ago when I, a 21-year-old college student on a first date with a 37-year-old man, reached for my wallet as a performative gesture, and he didn’t stop me. I, a broke undergrad who was in no way expecting to have to pay for my own meal on a first date with a man 16 years my senior, then had to awkwardly transfer money from my savings account to my checking account just to cover my portion of the bill. That was the first and last time I ever paid for anything on a date, and I have since dispensed with even performing the faux wallet grab.

I bring this up because the age-old etiquette question of who should pay for a date has once again reared its tired head thanks to a recent TikTok in which Toronto-based divorce lawyer Justin Lee gives his take. According to Lee, the man should always pay for a first date — but not for any of the reasons you may think. Lee isn’t concerned about chivalry or old-fashioned values or any such nonsense. Rather, Lee says men should pay as a “litmus test” to see whether or not their date is “entitled.”

“Let’s say, at the end of the date, you pull out your wallet and you offer to pay. And your date just sits there, expecting you to pay, as if that is the obvious course of action,” he says in the video. “You just learned that the person in front of you is entitled, and frankly, has the audacity to expect a near stranger to pay for them. Just imagine how someone like that would treat their significant other.” Thus, Lee concludes, “For a low, low price of $20, $30, $40, you learned that the person in front of you does not have the basic courtesy to pretend to offer to pay. And therefore you should never go on another date with them.”

It should come as no surprise that I am the kind of “entitled” woman who does, in fact, expect a man to pay for a date. (And not just the first one, mind you.) And no, I won’t even pretend to offer to pay anymore. This is a luxury I’ve been afforded, in part, because I have actively chosen to put myself in situations in which the expectation that a man pay is a reasonable one — e.g., sugar dating arrangements or other dynamics in which a significant age and income gap is present.

Regardless of your general opinion on the “who should pay” question, many people would probably agree that the awkward encounter with the 37-year-old I described above was, at best, a bad look for the guy involved. Many would probably also agree, or at least be willing to concede, that he should have paid given the power imbalance inherent in our age and income disparity.

But what we often fail to recognize in the illusory progressivism of modern society — at least in the context of the “who should pay” debate — is that there is always a power imbalance inherent in any relationship between a man and a woman. Despite undeniable progress toward gender equality in recent years, decades, centuries, etc., our society remains a deeply patriarchal one. We know this. We see it every day, not just in the persistent gender wage gap, but in every single double standard to which women are expected to conform just to get by. Be sexy but don’t be promiscuous. Be beautiful but stay humble. Be confident but don’t be aggressive. Don’t depend on a man but don’t out-earn him. Don’t age, period. Let a man take control, but don’t ever expect anything from him. Know your worth but don’t be “entitled.”

Some might argue that a woman paying for herself is a way of subverting this power imbalance. I, however, see the expectation that a woman pay, or at least pretend to pay lest she come off “entitled,” as just another way of telling women to sit down, shut up and expect nothing — yet another patriarchal control tactic designed to talk women out of exercising what little power we’re actually granted in an unjust society that values us largely (and very, very briefly) for our youth, beauty and sex appeal.

I’m not pretending this is some kind of feminist rallying cry, but merely a measured and practical response to being born into a society in which the deck was stacked against me from birth. I live in a sexist hellscape in which my value as a human being — particularly to the opposite sex — is measured almost entirely by my adherence to impossible standards of youth and beauty. In exchange, I get my shit paid for. That’s the deal, buddy.

That said, I do see Lee’s point about the value of demonstrating basic courtesy by at least pretending to pay. Being the self-serving opportunist that I am, I certainly understand that you catch more flies by not acting like an entitled bitch. But there are other, and arguably better, ways to express gratitude and humility than by practicing the transparent pageantry of the faux wallet grab. For example, you could thank someone for paying. A sincere thank you, in my opinion, far outweighs a performative wallet reach in terms of demonstrating appreciation and modesty.

Now, do I believe that some women genuinely prefer to pay for themselves and find it “empowering” and whatnot? Yes, certainly. Do I think those women are kind of stupid for not choosing to leverage what little power this bullshit system grants us to their advantage? Yes, yes I do. But how other women choose to squander their money and the precious bit of power the patriarchy throws our way is really none of my business. If you want to waste your money and what little privilege you’ve been afforded as a woman in this world, then by all means, go off queen. But any dick who has the audacity to demand women participate in this bullshit little charade lest they offend a man by appearing “entitled” deserves to have his ass dragged to hell and back. Also, he owes me dinner.

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