Attention, straight men dating women: Here's why they still — yes, still — expect you to pick up the check

Even Tucker Max has strong words for men who refuse to buy a meal—and it's not about money at all

Published August 28, 2015 8:04PM (EDT)

  (<a href=''>studiocasper</a> via <a href=''>iStock</a>)
(studiocasper via iStock)

Aside from whether men should hold the door for women, few seemingly frivolous issues have fanned the flames of anti-feminism as much as who should pay for dates between men and women. It’s a subject that seems to never die — see yesterday's Guardian feature on "Paying while dating" — because there are always a subset of men who insist that it’s absolutely unfair that as the world has gotten closer to gender equality, men are still expected to pick up the check. A 2014 NerdWallet study found that 77 percent of over 1,000 U.S. respondents expected men to pick up the check on a first date. Most likely, they will continue to be—perhaps not forever, but certainly for the here and now.

Why? News flash: it’s not about the money, it’s about what the money signifies. “The man should pay on the first date, always. It's meant to set the tone—that this is and was a date, not a networking opportunity or a new friendship,” founder of online dating concierge service eFlirt and author of "Love @ First Click," told Salon. “It speaks to a man's values and shows that he is a gentleman. Most first dates are just a few cocktails, so this shouldn't be a burden for men. Beyond a first date, the rules change a bit though and it depends on what you do together. For example, if it's dinner and an after-dinner cocktail for a second date, it's great for the woman to pay for the cocktails at the second destination. Or, she could plan and pay for the third date. Ultimately, paying the bill on a date shows appreciation. It's a gesture to let someone know you're interested in them and appreciate them. That's why I never suggest splitting the bill. A date should feel like a treat and it doesn't when it becomes an accounting transaction.”

I have to agree based on my own experience. Showing you’ve thought about the other person is what matters, and on a first date, paying is a way to do that. If you don’t have a lot of money, you can choose an inexpensive date so that you can cover the costs. I once went on a date to a free comedy show with a guy I met online. There were plenty of reasons the date was disastrous—think dead silence for up to ten minutes at a time—but the real rock bottom moment for me was when I said I was going up to the bar to get a drink and asked if he wanted anything (I wasn’t that thirsty but needed to break the tension). He said no but when I returned and reported that the bartender had generously comped my seltzer, he said he wished he’d known or he’d have ordered one! In that case, I was the one offering to pay, but instead of taking me up on it, he made himself seem like an extreme cheapskate. (Guys: don’t do this.)

Yet the who-should-pay decision is a conundrum, as dating and relationship expert Wendy Newman, author of "121 First Dates: How to Succeed at Online Dating, Fall in Love, and Live Happily After (Really!)," calls it, one that often leaves both men and women not completely satisfied. “When a man pays for a string of dates for strangers and experiences entitlement or isn't thanked or appreciated for these efforts it can burn him out. When a woman isn't treated, often times she doesn't feel special or cared for,” said Newman.

As further proof that it’s not about money, Los Angeles-based dating expert and radio personality Erin Tillman, who’s single, says “I’ve been on coffee dates with guys where they didn’t pay for my coffee.” That is definitely not the way to go if you want a second date—with Tillman or most women. Based on her own dating history and her clients’ experiences, Tillman told Salon, “if he doesn’t offer to pay, it’s definitely a turnoff.” As she sees it, “It sets a guy up for success. You don’t want to do anything that’s going to ruin your chances of dating someone.” She suggests the guy pay for the first month, or until you’ve established that you’re in a committed relationship.

While there are outliers, I think it’s safe to say based on everyone I’ve talked to and everything I’ve ever read about this subject that most women dating men do want them to pay in the beginning, to set the tone for what’s to come. As Helena Andrews remarked two years ago at xoJane, it’s about signaling whether you’re interested. A man who refuses to pay, or even offer, as one of her dates did, is making a statement with his wallet. Conversely, for her, if she pays, that’s her way of saying she’s not interested. “Usually if I pay for dinner, especially if it's the very first dinner out with a potentially romantic partner, it's because I want to leave as soon as possible,” wrote Andrews. “Not that I can't leave if someone else pays, but if I'm paying then I'm the one flagging down the waiter and twisting around in my seat for my coat. Bad sign. But when someone else is paying then I'm surrendering my time in a way that says, ‘What's next.’”

Men are aware of what this dynamic too. As New York-based tech entrepreneur Obinna Emenike, who always pays for his dates, told The Guardian, “If I think the date is going well, and you over-insist on splitting it then it will make me question myself. I might come to the conclusion that she doesn’t want to feel like she owes me anything.”

Even Tucker Max, who made a career out of sharing stories of hookups in books with charming names like "Assholes Finish First" and has recently reinvented himself as a family man, thinks men should pay, because that’s what women have consistently said they wanted. In his forthcoming book, "Mate: Become The Man Women Want," co-authored with evolutionary psychologist Geoffrey Miller, Ph.D., he makes the case for the man buying, because, as the pair write, women “are unconsciously looking for signals of your kindness, generosity, and material proof. Your picking up the check provides hard-to-fake information about your character and your resources, and that’s important information to have.”

In what will probably be shocking to fans who’ve followed Max’s sexist history with women but cause for applause from feminists, Max and Miller have strong words in their book for men who think women are using them for a free meal. “But a surprising number of men believe that paying for dinner and dates is nothing more than a thinly veiled exchange of money for sex. This is total fucking nonsense. The ‘men’ who perpetrate this line of garbage are angry misogynists who spend all their time trying to sleep with gold-diggers because their mothers didn’t hug them enough. Fuck those guys. If you’re one of them, get your shit together.” I’m happy to see him saying this, especially in light of a 2010 study that found “men were more likely than women to think that sex should be expected when a man pays for an expensive date,” as The Atlantic described it last year.

Yet Newman actually disagrees that men should always feel obligated to pay, even if they truly don’t want to. She says that if you’re a man who just can’t get past the idea that it’s unfair to constantly shell out for dates, “you should date women who will be fine in a 50/50 split from the start. They are a rare breed, but they are out there. You will be limiting the field, but at least you won't be resentful.”

Bustle writer Erica Garza, who’s now married, came to be part of that rare breed, even though for much of her dating life she expected guys she was with to “pay for everything, all the time,” no matter how long they’d been in a relationship. Yet over time, she changed her mind, writing. “I realized that if I wanted to be in a relationship where power was equally distributed, where respect was mutual, where each person in the relationship mattered and had value as a human being, then I had to shift my perspective about what paying for things meant. By expecting a man to pay simply because he is a man, I was inadvertently maintaining a history of repression, where men are viewed as in control and we women are still viewed as helpless.”

Part of the problem, as I see it, is that if you’re going on a first date, you really don’t know that much about the other person’s mindset. You don’t know how they’ll interpret your actions, so it’s probably a good idea to put your best foot forward. This doesn’t have to entail spending a ton of money, which seems to be part of the mythology of the gold digger. In most cases, women who want men to pay aren’t demanding a seven-course meal on date one. They want, as has been noted, to feel like the other person is thinking about them and doing something nice for them, that they’ve taken the effort, and one major way to do that, in the absence of other cues, is to fork over some cash, whether it’s for a latte, martini or movie ticket.

According to Davis, “Just because you're swiping on a screen doesn't mean that chivalry is dead. If you appreciate your time with someone, you should show her. When you ask a woman to split the bill, it will friend-zone you, because it doesn't feel like what just happened was a date. It's confusing to a woman. You don't need to pay forever, but you do need to pay in the beginning.”

But ladies, even if you expect him to pay, a little politeness goes a long way. “I’ve had a lot of male clients of mine say they don’t mind paying but they would really like it if a girl is appreciative and says thank you,” said Tillman. To go the extra mile, she advised women to offer to pick up the popcorn at a movie, or cover valet parking; whether or not he takes you up on the offer, he’ll be grateful.

So what about later on, if you’ve gotten past the who pays hurdle and are into dates three, four, five and beyond, or simply happily coupled up? In that case, Davis suggests alternating who pays. “It's something you only need to speak about once and then it becomes something that's automatic,” she said. “Splitting the check is never sexy. Even in my marriage, my husband and I alternate paying because being treated still feels special.”

Newman advises couples to “get creative” about how they will divvy up their finances — she certainly did. “There are all kinds of ways people can share the financial responsibilities but still feel like they are being treated,” Newman said. “After my partner and I had been dating for six months, we opened a checking account together. I deposited $200 a month into the joint account, and he paid for everything we did together. He got to treat, and I got to contribute by paying back a small part of the costs. Once we moved in together, we decided that I provided all the food in the house, and he provided all the food and entertainment outside the house.”

There’s room to be creative on first dates too. Again, it’s not just about dollar signs, as anyone who’s gone on a date with a rich but pompous guy can tell you. Maybe you have a connection to a special event or know a bartender or have the hookup on an exclusive party. I’m pretty sure that most women who want to be wooed would be more than happy to be taken somewhere exciting and different they never would have gone otherwise, even if you didn’t have to pay a cent for it. So yes, straight guys should be prepared to pay for a first date, but rather than see that as a sexist double standard, they can put their efforts into making their next first date memorable enough that perhaps it will be the last first date they go on for a long time.

By Rachel Kramer Bussel

Rachel Kramer Bussel is the author of "Sex & Cupcakes: A Juicy Collection of Essays" and the editor of more than 70 anthologies, including "The Big Book of Orgasms" and the Best Women's Erotica of the Year series. She teaches erotica writing workshops online and in-person, writes widely about books, culture, sex, dating and herself, and Tweets @raquelita.

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Dating Feminism Love Relationships Tucker Max