Who should pay on the first date? Everyone has a different answer

From generosity to fairness, the moment the bill arrives now carries more meaning than many people think.

Choosing who pays on a first date used to be a simple rule of etiquette, but today it’s one of the most debated topics in dating culture. Who picks up the bill is a big deal. While some people think it’s just about money, others see it as a sign of a person’s values, their interest in the date, and what a future relationship might look like.

We examine the subject through several lenses: men reflecting on how dating norms have shifted, relationship experts weighing in on what paying signals emotionally, and everyday people sharing their real-life expectations and experiences online. Together, these viewpoints show how a simple bill can reveal deeper ideas about generosity, values, and compatibility.

Who should pay on the first date?

In a discussion on Greatness Clips, Jay Shetty and Lewis Howes discussed how dating expectations have changed over the past 20 years. Lewis, who is a bestselling author and entrepreneur, shared a bit about his early dating experiences in St. Louis. He mentioned that he still remembers his sisters’ advice: “Make sure you’re a gentleman. Make sure you show up. Make sure you offer to pay.” Back then, “that was the belief”, he added.

However, Lewis sees that things have grown more complicated, especially with the internet’s influence. Some believe men should always pay. Others prefer splitting the bill, while still others treat it like a friendly outing, where everyone pays their own way. For him, paying is a choice of generosity. He feels responsible if he picks the restaurant, but views it as a “red flag” if a date immediately suggests an expensive dinner. He appreciates when a woman offers to split the bill, as it shows she cares, even if he doesn’t always accept.

Jay Shetty also added that this isn’t just about men and women; it’s about a person’s character. He pointed out that when he goes out with friends, everyone offers to pitch in, regardless of gender. However, he noted that it can depend on a person’s life stage. Both Jay and Lewis agreed that it’s important to focus on contributing to the relationship and to consider whether their values align with their date’s, rather than worrying about who pays first.

While Lewis and Jay offer thoughtful insights, therapist Lori Gottlieb provides a blunt take on relationships as discussed in The Diary of a CEO. For many women, if a man doesn’t pay on the first date, it’s not just a simple mistake. It’s a big turnoff, or what Gottlieb calls a “huge ick.”

Gottlieb shares a story about a client who enjoyed her date but was disappointed when the man suggested splitting the $5 coffee bill. Even though he wanted to see her again, she decided not to go out with him because she saw his lack of generosity as a problem. Gottlieb points out that not paying for the first date can be a warning sign that shouldn’t be overlooked. She explains that it shows how generous someone is towards the person they’re interested in.

She also emphasizes the importance of addressing such expectations and issues early in a relationship, so there’s a better chance for improvement. Gottlieb concludes by saying that it’s important for couples to talk about what paying for a date means to them. If they can’t have these kinds of conversations, both people could end up feeling confused about their relationship.

Scott Galloway, in a podcast with Jessica Tarlov, offers a different perspective on dating, suggesting that men should pay for dates to acknowledge gender differences in the dating scene. He points out that men often depend more on relationships for their emotional well-being, noting that single men can face challenges like loneliness and substance abuse more often than women. Galloway believes that, since women may feel more vulnerable regarding their safety and time during a date, paying can help balance the situation.

Jessica agrees with Galloway’s view but adds that paying for a date doesn’t mean a man has to spend a lot of money. Instead, she believes that a thoughtful approach within a reasonable budget is what truly matters. For her, it’s a simple and respectful way to kick off before the couple figures out how to handle their finances together in the future.

Public reactions

Men have also been turning to online forums to ask others how they handle the question of who should pay on a first date. In one such discussion on Reddit, one man offered a straightforward rule of thumb: “I would say whoever initiated the date, or whatever they agree on.” He described it as a practical approach that removes gender pressure and focuses on who made the plan.

Another person suggested staying financially independent early on: “Both should pay for their own food/drinks till the 3rd date.” This approach creates a more equal arrangement from the start, ensuring neither person feels indebted to the other.

The conversation also touched on how much location matters: “Depends on the country. In my country, it’s mostly the man who pays.” Cultural norms can greatly influence expectations.

One woman was very honest about how the gesture affects her attraction: “Let’s be real here…. If the guy doesn’t offer to pay, the woman will (likely) be really put off.”

For many, the offer to pay is still a significant sign of romantic interest. If a man pays for the date, it can influence how a woman perceives the relationship and whether she sees a future with that person.

Takeaway

The discussion about who pays on a first date can reveal a lot about how well two people might get along. In today’s dating scene, there are many ways to handle the bill: some might pay for everything, others might split it, or each person might contribute differently. This choice can show how generous someone is, how much effort they’re willing to put in, and if their values match yours.

In the end, there isn’t one correct approach, but there is an approach that works for you. If figuring out the bill creates tension on the first date, it might indicate that you and your date have different views and expectations for relationships.

50 Cents summed this up with a very simple rule of thumb. When asked who pays, he said the responsibility belongs to “Whoever’s idea it was to go on the date.” It’s hard to argue with that logic.