American writer, essayist, and media personality, founder and editor-in-chief of the platform Killer And A Sweet Thang, Eileen Kelly reflects on dating bills and explains why the question of “who pays” is not really about money, but about attention, a gesture of interest, and how we construct romantic roles at the very beginning of a relationship.
Last month, during a short holiday stopover in New York, I ran into a man who immediately recognized me from something I had done on a date years ago (a bad sign). “Oh my God,” he exclaimed in a British accent that somehow made it sound polite, “you’re the girl who wouldn’t split the bill. I’ve heard of you.” He turned out to be the brother of a man I’d once dated. Or rather, two men, because a few years later I inadvertently dated their other brother. (It’s very New York-y, and maybe a sign that I should broaden my dating pool beyond British majors with daddy’s money and psychological problems.)
Modern relationships: who should pay on the first date?
Laughing, my interlocutor asked if he could undo the damage his brothers had done and restore the family’s good name. He wasn’t trying to set me up, thankfully—he was already on a date with someone I knew. Here’s what happened. A few years ago, during a brief and sincere attempt at dating apps, I met the first brother at Raya. We agreed to meet for coffee in West Hollywood. I later learned that he was a failed actor with a serious drug addiction, but at the time it just seemed like really intense eye contact.
When I arrived for the date, he was already seated at a table, and the food and coffee had been ordered. I ordered a chai latte with masala chai, paid for it myself (an important detail, in retrospect), and sat down. We chatted about small matters for about twenty minutes, when he suddenly announced that he had to go walk his dog. Bruno, a small French bulldog who had been staring at me through the cafe window and, I was told, suffered from severe separation anxiety. This was surprising, considering how quickly his owner had broken up with me. My beau got up, left, and never contacted me again.
A few years later, at a party in Brooklyn through mutual friends, I met a man. He lived in a townhouse, packed with six other twenty-somethings, that felt more like a fraternity house than a home. He asked for my number, then asked me out. The accent was familiar—British again. I decided not to think about it.
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It wasn't until we sat down at a bar in Williamsburg on a cold winter's evening that he casually said, “I think you know my brother.” What struck me was not the coincidence, but how little I remembered about that previous meeting. Raya doesn't reveal names, and our coffee effectively ended before it even began. Still, I felt a little embarrassed that I hadn't realized this sooner, and at the same time a little surprised that my brother knew and wanted to meet me anyway.
We each had a beer. Then the bill came. He looked at me and narrowed his eyes. “We'll split it, right?” he asked. “Um, yeah, sure,” I said. But it made me angry. When he asked if I wanted to see him again, I said no. He seemed genuinely surprised. “You asked me to split the bill,” I said. “Yes.” “And…?” “Well, I thought you were a feminist,” he said. “If you didn't want to pay for the date, you should have asked me out to the park.” I tried to explain to him that it wasn't about the money, it was about the principle. And that somewhere along the way, his parents had clearly let him down.
The thing is, I can afford my own drink. I can afford dinner. I can afford a lot of things. What I can't afford is a lack of chivalry. I'm generous in relationships. I'm happy to pay for dinner, plan trips, pick up the tab, bake bread. But a first date is not just a gesture; it's a small but meaningful statement of interest. When you invite someone out, you're essentially hosting the meeting. It doesn't require luxury—just effort. I've dated men with very modest means who still knew how to make a woman feel cared for.
A friend once told me about her boyfriend, a man with a high-paying job who shared everything with her: flights, hotels, food. He would send her links to his airline tickets and expect her to buy her own. I looked at her and said, “How can you possibly get turned on by a man like that?”
When I’m being approached, I want to feel relaxed, not like a manager. I don’t want the evening to be broken up into small, inelegant tasks like splitting a Venmo bill. Romance, at least in the early stages, is a fragile illusion. It’s all about the mood. I want to leave a date thinking about what he said or how he made me feel, not about how to pay him back his $27.50.
Why paying the bill on a first date isn't about the money, it's about the gesture
Yes, I understand that paying can seem antiquated to a man and imposes an uncomfortable symbolic burden on him. (I also know women who don't care at all. After I made it clear that I would never see my other brother again, I did introduce him to a friend of mine—a slightly wild quasi-actress who is notorious in New York for reasons that would make your grandmother clutch her pearls. I was perfectly honest: “Just so you know, he made me split the bill.” They ended up dating for a few months. But given that women are still expected to get pregnant and give birth, I don't think it's unreasonable to ask a man to pay for the first drink. Yes, I could pay for everything, but I don't want to. And if that makes me notorious in some British families, so be it.
Based on material from: Vogue.com