Who's Paying for Your Next Date?

Guy meets girl. Flirting ensues. Fast forward to their first date. The banter is flowing, along with the wine; they may even be playing footsie and thinking about bedtime. But when the check comes, so does the evening's defining moment. Who pays?

Most women claim the guy should pay, regardless of who asked whom out or who makes more money. Like it or not, the tradition's a stubborn holdover from past eras when women couldn't afford to go halfsies. Lauren Henderson, author of Jane Austen's Guide to Dating (Hyperion, 2005), believes paying is a sign of respect. "Symbols are important, and a man who can't buy a woman dinner on their first date is a man who will be emotionally deficient at making a woman feel cared about," she elaborates. "Men need caretaking, but their need doesn't express itself in having dinner bought for them. Men want their ego bolstered by feeling strong, capable, and necessary."

Memoirist Maria Dahvana Headley ( The Year of Yes, Hyperion, 2005), who became a dating expert at NYU, is more flexible. "Paying shouldn't be as much drama as people force it to be. When I was broke, I often paid anyway. It's nice to be able to buy someone a gift, even if it's just coffee," she says. "I got so used to guys not paying, I nearly passed out when one guy bought me a full meal, plus wine and dessert, and didn't eat any of my food. This was unheard of!"

But how do guys feel? My curiosity was sparked by blogger Derek Rose (derekrose.com), who's looking for more of a "partner than a princess." He's fine with paying for the first date, and even the second, but "if a girl hasn't offered to pay for anything by the third date, she better look like Angelina freakin' Jolie, or else it's 'Sayonara.' I don't have any desire to be a sugar daddy," writes Rose. Frequent dater Jackie Summers picks up checks to make a good first impression and be a gentleman. He explains, "We're guys; we like to be needed. The woman who insists on paying half is essentially saying she doesn't need a man, she needs fresh AA batteries."

Nearly every dating or etiquette guide weighs in on the topic, and almost all stick to the same story. Shelly Branch and Sue Callaway, authors of What Would Jackie Do? (Gotham, 2005), advise that the former first lady would never pick up a tab until she'd established her date as a serious prospect, as she did with JFK. As unequal as this system seems, it makes sense; it's almost impossible to gauge a guy's personality within the span of one date. This simple test weeds out the cheapskates.

I'll split the check, or even pick up the tab, as long as I really like the person across the table. It's also circumstantial; if I know my date makes three times more than me and he doesn't even offer to pay, I won't be amused. But I was recently on a date with a younger guy who's unemployed, and was more than happy to buy him a drink and go dutch on the movie. It really was my "treat." I liked doting on him, which is a large part of what's missing from the incessant scheming around who pays. The scheming is all about the end result—what paying will get you—rather than the pleasure of someone's company, adding unnecessary layers of drama to the dating game.

If a guy simply pays without making a big deal out of it, I'm impressed. It shows generosity and a bit of macho protectiveness that even my feminist leanings don't want to quench. I realize it sounds contradictory to demand equality but still want men to pay, but I'm not advocating being a dinner whore. Frankly, I wouldn't want to waste time eating a meal with someone I wasn't attracted to, even if they took me to Nobu. It's not the price per se so much as the gesture. I'm more likely to date starving artists than millionaires anyway, and if a date wanted to have a snowball fight or go to an art opening and then Crif Dogs, that'd be perfectly OK.

In law school, I dated an older and wealthier guy. He always paid, and I valued this convenience since I couldn't afford his taste in restaurants. It took me a while to see that aside from good sex and similar musical tastes, we had little in common. I wouldn't say I was dating him for his money, but the combined effect of his age and finances and the cultured, assured persona that went along with them kept me with him longer than it should have. I ate lots of sushi and jetted around in his BMW, yet when I woke up in his Westchester house I always felt a little empty inside. If we'd truly clicked, money wouldn't have been an issue.