Last month, during a brief holiday stopover in New York City, I ran into a man who immediately recognized me for something I did on a date years ago (never a good sign).
“Oh my God,” he said in a British accent that somehow made this sound polite, “you’re the girl who wouldn’t split the bill. I’ve heard about you.” He was the brother of a man I’d gone out with once—actually, two men, because I’d also inadvertently gone out with their other brother years later. (This is not incestuous so much as it is extremely New York, and also maybe a sign I should expand my dating pool beyond British trust fund kids with daddy issues.)
Laughing, my inquirer asked if he could make up for whatever damage his brothers had done and restore the family name. (He wasn’t also trying to pick me up, thank God; he was already on a date with someone I knew.)
Here’s what had happened: Years ago, during a short and earnest attempt at using dating apps, I’d met the first brother on Raya. We agreed to get coffee in West Hollywood. He was, I would later learn, a failed actor with a serious drug problem, but at the time this just read as intense eye contact.
When I arrived—on time—for the date, he was already seated, the food and coffee ordered. I ordered my own chai, paid for it myself (an important detail, in retrospect), and sat down.
We made the usual small talk for about 20 minutes before he suddenly announced that he was leaving to walk his dog. Bruno, the tiny Frenchie staring at me through the café’s window, suffered from extreme separation anxiety, I was told—which was impressive, given how quickly his owner separated from me. My date stood up, left, and never contacted me again.
Years after that, I met a man at a party in Brooklyn through mutual friends. He lived in a townhouse crammed with six other 20-somethings that felt less like a home and more like a frat. He asked for my number, then he asked me out. His accent was familiar; British again. I chose not to reflect on this.
It wasn’t until we were seated at a bar in Williamsburg, on a winter night, that he said casually, “I think you know my brother.” I wasn’t stunned by the coincidence, ultimately, but by how little I remembered about that other date. Raya doesn’t show last names, and our coffee had effectively ended before it began. Still, I felt a little embarrassed that I hadn’t realized—and also a little weirded out that the brother knew and still wanted to go out with me.
We each had one beer. Then the check arrived. He looked at me and narrowed his eyes intently.
“We’re going to split it, right?” he asked.
“Um, sure,” I replied. But I was pissed off. When he asked if I wanted to see him again, I said no. He seemed genuinely confused.
“You asked me to split the bill,” I said.
“Yeah.”
“So…?”
“So, I thought you were a feminist,” he answered.
“If you didn’t want to pay for a date, you should have asked me to go for a walk in the park.” I tried to explain to him that it wasn’t about the money, but the principle. And that somewhere along the line his parents had clearly failed him.
The thing is, I can afford my own drink. I can afford dinner. I can afford many things. What I cannot afford is a lack of chivalry. In relationships, I’m generous. I’ll happily pay for dinners, plan trips, grab the check, bake the bread. But a first date is not just a gesture; it’s a small but meaningful declaration of interest. When you invite someone out, you are, in theory, hosting them. That doesn’t require extravagance, just some effort. I’ve dated men with very little money who still understood how to make a woman feel looked after.
A friend once told me about her boyfriend, a man with a high-powered job, who split everything with her: flights, hotels, meals. He’d send her links to his plane tickets and expect her to book her own. I stared at her and asked, “How do you even get wet for this guy?”
When I’m being courted, I want to feel relaxed, not managerial. I don’t want the evening to fracture into small, inelegant tasks like carving up the check on Venmo. Romance, at least in its early stages, is a fragile illusion. It’s all mood. I want to leave a date thinking about what he said, or the way he made me feel—not how to pay him his $27.50.
Yes, I understand how, to a man, paying can feel outdated, placing an unwieldy symbolic weight on their shoulders. (I also know women who don’t care about this thing at all. After making it very clear that I would never see the second brother again, I did set him up with a friend of mine—a somewhat wild quasi-actress, infamous in New York for reasons that would make your grandmother clutch her pearls. I was brutally transparent: “Just so you know, he made me split the bill.” They ended up fucking for months.) But given that women are still expected to shoulder pregnancy and childbirth, I don’t think it’s unreasonable to ask that a man covers the first drink. At the very least, it keeps the phones off the table.
Yes, I could pay for everything—but I don’t want to. And if that makes me infamous in certain British households, so be it.