Sorry for being stingy. I’m a woman. When I stop at a convenience store with a man I’m dating, he sometimes stays in the car and asks me to “pick up some coffee.” Even when I buy it, I feel a little disappointed that he doesn’t reimburse me for the coffee.

I’m Saito, a columnist♪ This may sound a little odd, but as Mac said, “When it comes to sales, the person being sold to is the one who loses（笑).” That’s why, even in dating and human relationships, I find myself keeping track of my emotional deposits and withdrawals, and I feel excessively resistant to having someone spend money on me. If I receive one, I feel I have to give back two… I suppose some men think, “If I’m giving her ten, she should at least give me one in return.” But the moment they make that demand, it goes back to being one-to-one. Sorry for the explanation—it sounds like sales coaching. There are also poor people around me who show no hesitation about “accepting things,” and even say things like, “He’s got money, so we might as well make him pay.” Well… nobody tells them, “That attitude is exactly why you never grow.” I imagine the same applies to you, too. Society is a harsh place, unlike school.

Maezawa from the Corporate Planning Office here as well. I can see why that would leave you feeling uneasy. There’s probably no one right answer, but when he asks you to go buy coffee, you could try saying, “I forgot my wallet today…” That way, he’ll probably give you the money. After that, it’s like Pavlov’s dog. If you repeat it a few times—or a few dozen times?—he’ll probably start giving you money without you even having to say you forgot your wallet. Even if you do have your wallet, I think it’s fine to act as though you don’t. When you receive your allowance, you’ll probably have to put it straight into your bag instead of your wallet, but you’ll just have to live with that.

I’m Meg, a female member. I haven’t had an experience like that yet, but I’m sure I would feel just as unsettled. I thought Adventure Merchant’s comment, which got to the heart of the question, was excellent. Thank you for such helpful advice. When you explain your feelings clearly in words, you can also get a sense of the man’s true character. I hope he isn’t stingy.

I’m Date◎Yume, a male member. Actually, I do that sometimes too. In my case, we’ve known each other for a long time, so I just hand her my wallet. The other day, she cheekily said, “I kept the change,” and I’d just told her, “Sure, go ahead.” (laughs) I think it really depends on the person. I’m a low-income member of the dating club, but plenty of wealthy people can be pretty stingy too. (laughs) Though I wonder if people like that actually use dating clubs... If you two have been seeing each other for quite a while, why not say “wallet” and hold out your hand the next time you meet? (laughs) P.S. The story about Mack and Saito’s sales pitch is a good one. It’s a great little lesson in human nature. (laughs)

I’m the columnist “Adventure Merchant.” I don’t think this is a matter of which side is right or what things are supposed to be like. It comes down to personal values. Some wealthy men are very particular about not making a woman pay for even things like coffee. Others may think, “I’m already giving her an allowance in the tens of thousands of yen, so it’s only natural for her to cover something like coffee. It might even make us feel more comfortable with each other.” Women feel the same way. Some may think, “Since I’m receiving that much money, I should at least pay for the coffee or parking.” Others may feel, “I want him to cover the coffee too.” So the real issue in your question isn’t whether “wealthy men don’t feel the need to give anything back.” It’s that you personally feel stressed about paying for your own coffee. A relationship that causes you stress isn’t healthy, so set aside for the moment what things should ideally be like or what the man might think. Try telling him something like: “I’m sorry—I know this might make me seem stingy, but would you mind covering the coffee (or parking) fee?” I think it’s important to communicate how you feel.