The other day, a woman in her 20s told me she wanted to go to a high-end French restaurant, so I took her to one in Ginza. During the meal, she loudly said, “I’d like about ¥50,000 in allowance today,” and all the other diners turned to look at me at once, which made me feel very uncomfortable.

Question 1 I’ve never had an experience like that. However, for a first-date offer, I always choose a private or semi-private room. We discuss the allowance and other terms somewhere no one nearby can overhear us, confirm that we agree, and then go into the room. Question 2 Why ask that all of a sudden? Is that what you really wanted to ask? I suppose it’s up to the club to decide. Their website says the membership requirement is being 45 or younger, so you might want to contact the club directly. Of course, there’s still a possibility you won’t pass the interview.

If you choose someone based solely on looks, whether she’s in her 20s or 50s, she may lack a basic level of social awareness. Looks matter, of course, but before taking her to a nice restaurant, you should get a sense of her manners, behavior, and upbringing. The other day, when I went to the Marriott in Wakayama, the woman at the table next to us kept talking loudly the entire time… While we were sitting side by side, chatting and looking out at the ocean, she kept staring at us and whispering to her companion. It reminded me of the man saying under his breath, “This isn’t a hostess club.” You can usually get a pretty good sense of someone’s upbringing when you meet them, can’t you? As long as she isn’t overly giddy or immature, I think she should be fine.

I edited out the parts unrelated to the question. > “I always pay the allowance.” That’s probably where the discrepancy lies. When someone always pays, there’s no reason to go out of your way to ask how much they want. It seems the situation is that, even though this isn’t their first date, he makes excuses not to pay—or pays less than promised—so the woman feels she has to speak up. In the first place, “I always pay an allowance” and “how much I pay” are two separate issues. And honestly, the fact that you worded it this way already makes you seem untrustworthy. If you don’t want the other person to ask, just say from the start that you’ll pay ¥50,000, or state the amount clearly. The fact that she goes as far as to mention the allowance amount even though this isn’t your first date suggests that she sees you as seriously problematic, untrustworthy, and someone whose words don’t match his actions. I think you should properly acknowledge that about yourself. (Though I suppose because you can’t recognize it, you end up thinking you’re right and the other person is the one acting strangely.)

No, lol. To begin with, I’m assuming you change the allowance amount every time, right? I think that system is fundamentally flawed. If you’re in a relationship where you discuss money every time, then it’s become part of your routine, so it might just slip out. Usually, I think you decide on the amount at the first meeting and don’t discuss it afterward. Even though it’s a financial arrangement, you both naturally develop an unspoken understanding not to bring it up. Then sometimes you forget to hand it over, and it carries over. Of course, you give it all at once later, but when several payments pile up, they might laugh and say, “Whoa, that’s a lot, lol.” As for Question 2, that’s what you’d normally expect. There might be some kind of “裏ユニバース” (a nickname read backward as “スーバニ湯”) squad that takes on dirty work and gives a dropkick to the back of a lovely woman in her fifties who spends all her time studying but never makes any progress. But, more seriously, you’d better watch what you write—you might get erased. I’m talking about that love-call-like message in between, by the way, lol. Taro