It’s the first date. You’re sitting across the table from a nice, attractive woman chatting the evening away over an adult beverage. Perhaps you ordered that hummus plate for something to nosh on (though you pick at it only because it gives you something to do. You’re way too nervous to have much of an appetite.). After about ninety minutes, the server comes by and drops off a small, black leather folio. You eye the folio nervously. So does your date. Maybe ten seconds pass, but it feels like ten minutes. The beat hangs in the air like a high fly ball to center field. Stalemate. Finally, the silence is broken when she says, halfheartedly, “You want to split this?”
I always pay on the first date.
Always. In fact, when the bill comes, I pick it up so fast the woman doesn’t even have a chance to make a cursory move toward the bill. Asking, “Who pays on the first date?” sounds like an antiquated question for days gone by when women and men did the dance by a specific script. Years ago the answer was “The guy. Duh.” But in today’s online, connected, independent, equitable world the answer seems like it should be more nuanced. Should you split? I mean, you don’t want your date to infer that you think she’s incapable of taking care of herself. This woman sitting across from you can certainly afford to pay her half of the $25 bar tab.
But to me, this situation is not about who can afford what. It is about sending and receiving messages. So make your decision about what message you want to communicate before you make a conscious decision of what your action is going to be. This gives your actions at the end of that first night some purpose. Since I know the messages I’m trying to communicate and receive, paying is the right choice for me.
First of all, it’s a nice thing to do. This is not about money, it’s about the gesture. Why don’t you want to do something nice for someone? Are you a jerkface or something? Stop being that, then. If you’re concerned about spending frivolously, then don’t plan your first date at Metrovino (which I have done.. ugh.). McMenamins for happy hour is just fine. Or, hey, how about meeting at Moonstruck for a cup of hot chocolate? That’s fun, and it keeps bill under $10. The amount isn’t important. A woman worth getting to know is there to get to know you. She probably doesn’t care if it’s over a decaf latte at the neighborhood coffeehouse or a Filet Mignon at Ringside (and if she does bristle at your first date choice, isn’t that something you’d like to know?).
Insisting on paying also gives you information about her. Here’s an incomplete list of things I want to know about the woman I’m treating to a first date:
Does she offer to pay half?
I don’t actually expect her to pay half. In fact, I don’t expect her to expect to have to pay half. But I expect her to offer. To me, it means she has manners. If you want to get literal, this is what is actually being said:
Man: I’m signaling that I’m paying.
Woman: I’m going to offer to pay my half. While I am willing to pay, I hope that you will insist on paying the entire bill.
Man: I appreciate your honoring of the modern social custom of being willing to split. I acknowledge your manners. I will now pay the entire bill.
Woman: Gratitude.
Does she know how to accept a gesture?
One time, I had a ninety second negotiation (or was it an argument?) with a date about whether I would accept her money. She was literally waving cash in my face. I thought this very strange, and it screamed insecurity. Frankly, if a date puts up this much of a fuss, it’s probably just better to let her pay half. Suffice it to say, I didn’t call her back.
Does she thank you?
And I don’t just mean saying “thank you” at the table. Does she send you a nice text message after the date (probably the next day, but sometimes the same night)? If so, bingo. You have identified a woman with manners who is interested in a second date. My friend, you are off to a smashing start. (Women’s corollary: send a ‘thank you’ text within 24 hours if you like the guy. If not, feh.)
Sometimes first-date drinks go so well that the evening extends into dinner. In this case, the woman might offer to pay her half again (and she should), creating another potential awkward moment. Here’s how you respond: “This evening is on me. How about you get it next time?”
Smooth, Jack. Real smooth.
