‘I felt humiliated’: She slipped the waiter her credit card on her way to the restroom. Is it emasculating for a woman to pay for dinner on a first date?

I recently went on a dinner date at a Mexican restaurant, one of my favorites. Our total bill came to around $ 190 — we drank cocktails and a lot of wine — so I offered to pay the check. My companion, a 30-year-old public-relations representative, insisted on paying. In fact, she slipped the waiter her credit card on her way to the restroom. We’re probably making the same amount of money, given her lifestyle (she spent a week in Mauritius in January), but I feel like I should pay given that I chose the restaurant and it was our first date. 

Is it emasculating to allow a woman to pick up the dinner check? I felt humiliated, honestly. We got along well enough for a second date, even though I would describe her as quite a type A personality. There’s confident, there’s superconfident, and then there’s this woman. That’s an attractive quality, but as my father would say, “Everything in moderation.” He would also say, “You don’t get a second chance to make a first impression.” I felt wrongfooted.

A man should pay, at least on the first date. Am I wrong?

Still Single

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Dear Single,

One man’s emasculation is another man’s AirPod Pros AAPL, -0.84% — you could actually buy a new pair with the savings from your dinner date.

But back to your question: She either liked you so much that she wanted to pay for dinner, or she had such an awful time that she wanted to make sure that she was under no obligation or compliment to you. But whenever given the choice to choose between the most optimistic scenario or the most dastardly one, it’s usually better to choose the former. (Unless you’re considering buying a particular stock, and the company gives a bizarre reason for a sudden fall in revenue.)

By not giving you a choice in the matter, she saved you both from the kind of unseemly argument over the check that can take place on first dates. Some people don’t like surprises, especially if those challenge what they have been raised to believe. We all carry a set of values and beliefs and unconscious biases when we navigate the world. They could be something as small as who picks up the check on a first date. Your dinner companion cut through all three with one swipe of her credit card. 

I receive a lot of letters about dating etiquette, including who should pay the bill. This is my take: You walked out of that restaurant having saved $ 190, but you feel like you paid a heavier price — a threat to your masculinity and place in the world as the brandisher of the plastic on first dates. I don’t know whether you had a second date with this woman, but separate your pride from your manhood. Ideally, the latter should be less easily rattled than the former.

Social mores dictate that the man or the person who chose the restaurant should pay. The twinge you felt was the bending of those protocols. She also took the initiative and, as you put it, wrongfooted you by paying the bill behind your back. Some studies suggest that men, as outdated as it might sound, are conditioned by society to act assertive, which helps them be perceived as leaders in the corporate world. Literature like “The Book of Dares: 100 Ways For Boys To Be Kind, Bold and Brave,” by Ted Bunch and Anna Marie Johnson Teague, aims to counter that notion.

Social mores and protocols

I say this to help you understand why this is the way you feel. Your date passing her credit card to the waiter was generous. Somebody who did not have a good time and who never intends on seeing you again is not going to go to the trouble of paying the bill surreptitiously and, in the process, upending so-called gender norms, however outdated they may be. The fact that what is arguably a very big compliment resulted in your feeling “emasculated” has nothing to do with your dinner companion.

Most people agree that the person who asks for the date should pay, according to a recent survey of 2,000 adults by the Harris Poll. Some 78% of men and 68% of women believe that men should pay for the first date. However, 77% of women and 52% of men say the “asker” should pay. But that does not account for individuals and your particular case where one person felt strongly enough about it to break those “norms” and pay for a very expensive meal. Same-sex couples at least get to avoid this gender-based dilemma. 

Yes, the person who chooses the restaurant should probably offer to pay, especially if it’s an expensive venue. Last year, one woman wrote to me about the opposite problem: She was upset that her boyfriend asked her to go Dutch. Her exact words: “I don’t want him to get used to me paying for my own meals.” Then there’s the guy who “forgot” his wallet and took the receipt for his taxes, and the single guy who spends $ 600 a month taking women out for dinner. Dining with friends can be equally problematic, especially if one party chooses a significantly cheaper dish.

But here’s the main message your female companion was probably sending you: “I like you enough to pay for this because I feel confident that I will see you again.” Of course, you would probably know best how the dinner itself went. It would be a shame to allow this act of faith and, frankly, magnanimous maneuver to not leave you with the same confidence in yourself, and in your qualities as a dinner companion. Ask her out for a second date and, this time, you can pay.

You can email The Moneyist with any financial and ethical questions at qfottrell@marketwatch.com, and follow Quentin Fottrell on X, the platform formerly known as Twitter. 

The Moneyist regrets he cannot reply to questions individually.

Previous columns by Quentin Fottrell:

My in-laws gave us $ 300,000 and are on the deed to our home. Now they insist we give our niece $ 125,000.

My estate is worth millions of dollars. How do I stop my daughters’ husbands from getting their hands on it?

‘They have no running water’: Our neighbors constantly hit us up for money. My husband gave them $ 400. Is it selfish to say no?

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