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My best friends tell the story about when they met. He was her teaching assistant at university and he noticed her right from the start. He asked her out several times and she refused. My friend is a die-hard feminist. When she finally agreed she said she would go out on a date with him, but that she would pay her own way. His response? Great! Then we can do twice as many things. 

They only got married because he got a job at a teen summer camp that would not hire someone who was “living in sin.” So they had a small ceremony at their home with a few close friends and their sheep dogs. Throughout the marriage they have shared all of the expenses of running the home, buying groceries and furniture, and paying for holidays. They each have their own investment accounts. I have never known two more happy people than these two.

I personally pay my share at the beginning of every relationship. Simply because there is still the male societal expectation that women are like pop dispensers: You put in some money and you get what you want as a result. At least, that’s how I see it. When you start out paying up front for yourself, you are telling the person you are going out with that that value judgment is off the table, and that there is no expectation when the date is over. 

Who do you think should pay?

Admiring Friend and Occasional Dater

Related: ‘This guy grifted me hard’: My date chose an exclusive L.A. restaurant. After dinner, he accepted my credit card — and we split a $600 bill. Shouldn’t he have paid?

“Choosing a partner is potentially the biggest financial decision you will ever make in your life, especially if you choose to divorce. So make it wisely.”


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Dear Admiring,

If a man asks a woman out on a date, and he chooses the restaurant, he should at least offer to pay. If a man asks another man out on a date, and he chooses the restaurant, he should at least offer to pay. If a woman asks another woman out on a date, and she chooses the restaurant, she should at least offer to pay. If their date says, “No, let’s go Dutch,” fine. 

If their date says, “Thank you, that’s very nice of you,” and let’s him pay. That’s OK too. I feel particularly strongly about this if the person chooses a very expensive restaurant: You can’t expect everyone to fork out $100 or $200 or more for a meal. If you do, you’re living in a bubble and you’re not taking the other person’s feelings into consideration, and that’s a red flag.

Of course, some people — like this woman — expect their partner to pay for everything. And some men don’t even like their wives to work. Others say they like to go to work to get away from their partner. What does this tell us? Not a lot really, except to say that if everyone felt the same about working and paying for dinner, the world would be a very dull place.

I heard another “meet cute” story recently where a couple met on a night out and swapped numbers, and he never called her. So she thought, ‘We had a great night, I’ll find him and ask him why he never called.” He lived in another city, and she tracked him through his work, and sent him a letter. Turns out, he had lost her number. They’re now married with three kids.

Everybody has a different level of expectation and confidence, and a person who has strong principles about paying their way, like your friend, should find a romantic match who appreciates and supports that. Choosing a partner is potentially the biggest financial decision you will make in your life, especially if you choose to divorce. So make it wisely.

Who pays on the first date, and the consideration and respect that they show for their partner’s decision, is a good guide for how the relationship will progress. Here is an experiment: Bring your date to a restaurant with slow service, sit back, and see how they react. They may learn a lot about how they operate under pressure if things don’t go their way.

More columns by Quentin Fottrell:

‘I want to meet someone rich. Is that so wrong?’ I’m 46, earn $210,000, and own a $700,000 home. I’m tired of dating ‘losers.’

My dinner date ‘forgot’ his wallet and took the receipt for his taxes. Should I have called him out for being cheapskate?

‘I spend $600 a month taking women out for dinner and drinks’: Does the man always have to pick up the check on a first date?

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.

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