The Lost Art of Picking up the Check, Always

John Springer Collection//Getty Images6 min readAnytime my wife and I eat or drink out, I pay. When she says it’s time to go, I flag down the service staff, take the check, and squint while I pretend to itemize the bill. She checks her phone or looks around the room as I hand off the card and make small talk with the server. When it comes back, I pass the receipt across the table. My wife is vastly more capable than I am at simple arithmetic, so she handles the tip and keeps a copy.On paper, none of this dance matters. We’re married. We share 100 percent of our finances. Neither of us can really “buy” the other dinner at this point. But both of us see it as nonnegotiable that I put down the card. It’s the same reason I open car doors for her or pick her up from the airport. None of it is necessary, but it’s one of the million little things that quietly adds up to being a man—the things that, if I didn’t do, especially early on in our relationship, she’d find someone else to do for her.Recently, the Esquire staff went back and forth on the particulars of when a man should grab the bill. We had just published a story about men buying women Ubers, which made us question the deeper implications behind such new rules of dating for men. Talking points included overwrought takes on right-wing tradwifeism and the regression of feminism; shock that the foundation of a heterosexual relationship can hinge on a straight man’s willingness to grab a bill; and the idea that the guy should always pay but needs to see some act of faux-commitment—in other words, the purse pump. Not once has bank account balance or gender politics ever crossed my mind when buying my wife a martini or paying for Uber fare. Yet the topic has turned into dozens of think pieces and TikTok videos that stick well to the algorithm. It all makes me, a married Gen Z man who was last single when he was near destitute, feel a bit like Yeats’s falconer watching the world spin out of control.So, I would like to put a marker down and offer a word of advice for the men of this world: You grab the bill, and you grab it as much as you can. You don’t do it for any reason other than it is the polite thing to do. You don’t have to put yourself in debt by taking every date out for a tasting menu. But what’s wrong with overextending yourself in the name of love—even just a little bit?United Archives//Getty ImagesMyrna Loy and William Powell share a drink in The Thin Man. Whose character paid the tab, you think?Male chivalry has become a hot-to-touch topic. The loudest voices in its favor are the Internet’s most divisive figures. The simple suggestion of male politeness—in this case, politeness toward women—has become a Trojan horse for manosphere influencers like Andrew Tate to scare young men toward their hegemonic interpretation of masculinity. “Beauty is a commodity,” Tate says, and therefore you should be expected to break out your wallet when interacting with “high-value women.”Though that is an obviously heinous point of view, I don’t think it strays too far from the terminology and attitude I read in The Cut. The magazine has reported on the extremes of women who subsidize their deadbeat boyfriends and the “good man shortage” that sends high-earning women to high-retainer matchmakers. On the other hand, The New York Times has reported on the very real concern that Gen Z can’t even afford a first date.In its story on the “good man shortage” and the jobs of professional matchmakers, The Cut discusses “recruitment” and includes quotes on “dating with ‘full-time job effort.’” Even within my own circle, dating talk boils down to the strictly financial. When close friends have asked for dating advice—one of them single in his 20s, the other divorced and back in the game at 40—they pose questions along the lines of, “Am I an asshole if I feel like a woman should pay, or at least offer, to show she’s interested?”Articles and conversations like these hint at what I think is wrong with this entire moment of discourse: It’s all about money. What was once a dinner party conversation starter—“Do you start splitting the bill on the fifth date or the tenth?”—has turned into a platform for takes on why women should feel grateful to be provided for, or, conversely, to express shock and awe that men want to show some amount of chivalry.Men cannot use capital to bend love to their will. Melinda French Gates and MacKenzie Scott (formerly Bezos) divorced their rich—not just currently rich, but like, historically rich—husbands after decades of marriage. After becoming one of the wealthiest women in the world post-Bezos divorce, MacKenzie Scott has averaged billions of dollars’ worth of charitable donations every year; I don’t think you can get a more apt metaphor.And besides, many cautionary tales exist across movies of the last century, books and plays of the middle of the last millennium, and epic poetry of antiquity. My favorite example is Citizen Kane, Orson Welles’s debut and magnum opus. One of the many great lines in the movie comes as Susan Alexander Kane—mistress-turned-wife of media mogul Charles Foster Kane—finally walks out on Welles’s tragic millionaire. “That’s money, it doesn’t mean anything,” she says. “You never really give me anything that belongs to you, that you care about.”Archive Photos//Getty ImagesOrson Welles and Rita Hayworth out to dinner circa 1945, a few years before their divorce. Maybe he should have taken his own advice from Citizen Kane.The key word here is give. To give is not to purchase for, it’s not to hand over with the expectation of something in return. To give is to let go completely, to share a little piece of yourself.In his book In Praise of Love, French philosopher Alain Badiou develops a theory called the “Scene of Two.” Love, as Badiou sees it, has to be cared for and developed. It’s a two-person scene that requires input—real input, not just money—from both sides. Badiou is also quite practical. “[Love] is an existential project: to construct a world from a decentered point of view other than that of my mere impulse to survive or reaffirm my own identity.” By that he means love is not the transcendental merging of beings or combination of two-into-one, as poets might write. Badiou’s love is about constantly having—or having the pleasure—to see the world from your secondary point of view, a view that is not, and can never be, the exact same as yours.No doubt Badiou would find we’ve twisted the simple kindness of paying the check into a financial game in which paying for things wins respect and admiration. Obsessing over finances is too often focused on the internal: How much did I pay, how does it make me look, what return do I get on my investment? Or, to think that a woman should feel an obligation to a man because he pays for food or shelter is antithetical to Badiou’s practical, actionable ideal.To give is not to purchase for, it’s not to hand over with the expectation of something in return. To give is to let go completely, to share a little piece of yourself.Case in point: When my wife and I started dating in college, neither of us had a lot of money. For a few semesters, she worked as a waitress, and I was a delivery driver. Since customers tipped her properly, she always had more spending money. We would go round-for-round on casual drinks and meals because neither of us had enough to cover two adults’ worth. But when it was date night, she wasn’t allowed to pay.I’d call her to set a time for Thursday, then walk into Kroger as it was closing, grab a cheap pinot grigio, and sneak three cheeses into the pocket of my chore coat. (I never thought much of it—necessity breeds invention, I guess—but she has since told me she found my transgressions incredibly romantic.) When I’d arrive at her place, we’d do nothing more than sit on the stairs behind her apartment, face a lot with a view of the night sky, drink bad wine, and eat manchego. Those dates only cost $10, and she knew it. She still married me.I don’t know what your finances look like, but quite frankly, it doesn’t matter. Pay for people in your life—especially romantic interests but also friends and family. Do it silently and a little more recklessly than your comfort zone allows. I don’t have a hard-and-fast rule about when you should stop paying and let whoever you’re seeing start treating you, but what I will say is this: Think of the amount that you would normally spend on a date. Then, multiply it by one and a half. A movie and drinks turns into a movie, drinks, and a car home for her. At a fancy dinner, ask for the ten-year-old bottle instead of the five. And when you do, don’t make a big deal out of it. Because it isn’t. In a few weeks, you won’t remember how much that night out cost—but your date will never forget your conviviality and generosity. Repeat that enough times, and she just might agree to marry you.