I recently met a man who had made me an offer.

Since the man approached you saying, “Please date me,” I can understand why you feel the “getting to know each other” stage should already be over—meaning he’s looking at this as something longer-term, not just one or two meetings. So why would it still be pay-per-meeting, where there’s no guarantee of seeing each other again? That’s the part that doesn’t sit right with you, isn’t it? The meaning behind his “Please date me” is different from what you mean by “dating.” To him, it probably means something like, “Let’s meet again next time too—if I’m in the mood.” By the way, I currently live with a woman who does papa-katsu, and until very recently, I was still paying her on a pay-per-meeting basis. Since we live together, you could say we were “dating” in the sense you mean, but I never found anything strange about paying per meeting. I’m thinking of switching to a monthly arrangement starting this month, though, because sleeping together has made it hard to keep track of what counts as one “meeting” when I get tempted and initiate things. For example, what should happen if I don’t have intercourse but touch her and make her climax? Also, generally speaking, “Please date me” means, “I want us to be boyfriend and girlfriend without exchanging money.” Your interpretation is the minority one. You should be aware of that.

Monthly arrangements are difficult. For example, if you agree to meet three times a month and set up a monthly arrangement for ¥300,000, it’s rare to find a woman who will consistently meet three times every month. If she gets her period on the day of a date and can’t go out, the month will usually end with only two meetings—unless she strongly says, “I want to reschedule. I definitely want to keep our promise of meeting three times a month.” That averages out to about 2.5 meetings per month over the course of a year. Do you actually keep your promise to meet the agreed number of times under the monthly arrangement? You probably don’t, right? I can tell from the way you wrote your question. I get the impression that you’re the type of woman who prioritizes cost-effectiveness and tries to reduce the number of meetings as much as possible after entering into a monthly arrangement. If I’m wrong, I’m truly sorry. Once you become an experienced papa (a male supporter), you start to instinctively recognize women who give off the kind of impression you do. That’s where I am these days. If I feel even slightly uncomfortable, I won’t offer a monthly arrangement in the first month. I’ll wait and see how things go for a while. And the discomfort you feel at the beginning is usually correct. The only women I still have ongoing monthly arrangements with are those who agreed to one on the very day we first met—when we only had dinner and there was no adult relationship (intimacy). Even without knowing whether we’d be physically compatible, I had a gut feeling during that dinner date: “This girl is trustworthy.” That intuition turned out to be right. We’ve continued for a long time, and I can’t see any reason for us to part ways. Whether she gets a boyfriend, gets married, or has children, I’ll probably continue meeting her under a monthly arrangement for as long as she wants to. After reading my answer, you’ll probably get irritated and post a follow-up question saying, “Your answer is wrong.” That reaction is the answer. I would never offer a monthly arrangement to someone like that. On the other hand, if you’re able to reflect and think, “Maybe this applies to me,” then perhaps the next papa you meet will offer you a monthly arrangement at your very first meeting.

> Don’t you think it’s okay to wait until you’ve gotten a better feel for him? They may have used “seeing how things go” because that can mean different things to each person, whereas saying they’re “dating” or “seeing each other” leaves less room for misunderstanding. For women, many feel that the getting-to-know-you stage means no adult relationship (intimate) yet. For men, many feel that they can’t really know unless they have an adult relationship. So when they agree to meet again to “see how things go,” the woman may be thinking it will be dinner only (no intimacy), while the man may have already decided they’ll go to a hotel afterward. Even if that doesn’t happen, I don’t think anyone would actually tell the other person, “We’re still in the stage of evaluating you.” Instead, as they meet a few times, they naturally figure out whether they want to keep seeing the person, or whether they think, “He’s a nice person, but I don’t really want to see him again.” With a monthly arrangement, however, it becomes a different kind of evaluation. There are actually quite a few women who take the money and then become unreachable. If this were an ordinary contract, it could be serious enough to result in a lawsuit, and in some cases even arrest for fraud. That said, people worry even with ordinary contracts. For example, when renting an office, you may need a guarantor or a guarantee company, along with various other arrangements. You would probably feel uneasy too if, despite agreeing to a monthly arrangement, the man said he would pay after the month was over. And if you had ever been abandoned by a man after paying him once, you might naturally want one month’s allowance upfront for a monthly arrangement. Because of these circumstances, it’s difficult to pay upfront on a monthly basis until you trust that the other person won’t disappear. The general understanding is that pay-per-meeting is better for both sides. People who have never been abandoned in the past may agree to a monthly arrangement easily, but many of them eventually get betrayed by a woman and change their approach. If you really prefer a monthly arrangement, you could say, “I’m okay with being paid at the end of the month,” and some men might agree. However, you could end up going to a hotel about eight times in one month and then receive none of the promised monthly allowance afterward, with the man becoming unreachable. That’s why I wouldn’t recommend it.

There probably aren’t many men who want to date a monthly papa. A monthly arrangement suggests that both parties are experienced with papa-katsu (compensated dating in Japan), so quite a few men may prefer to avoid women who are too accustomed to it or seem like pros. I once offered to give a club companion a month’s allowance when I knew we probably wouldn’t be able to meet much that month. She got angry and said, “I’m not that money-minded!” Girls who aren’t used to papa-katsu, or who are new to it, probably wouldn’t immediately think of proposing a monthly arrangement. They can’t even comfortably bring up the subject of an allowance… I don’t think you need to calculate everything so carefully… You’re going to become a papa-katsu professional…

Everyone has their own way of thinking, so I can’t say whether my view matches that man’s, but I hope this gives you some perspective. I think the reason he wants a pay-per-meeting arrangement rather than a monthly arrangement is that he doesn’t yet know how your relationship will actually develop. To keep it simple, let’s use the number of times you meet as an example. At the first meeting, you don’t know whether you’ll eventually see each other once a month or five times a month, do you? Some people may think a monthly arrangement is like a subscription, meaning you can meet as often as you want, while others may think it means meeting only a certain number of times per month. If misunderstandings can arise just over how often you meet, there can also be issues involving the frequency of communication and various other expectations that weren’t met. By deciding in advance how much he’ll give you each time, you can avoid many of these “That’s not what I expected” situations. After meeting several times and getting to know each other better, you’ll gradually get a sense of what the other person has in mind. Those misunderstandings will become less likely, and even if they do happen, you’ll be able to discuss them. I think that’s what the other papa (male supporter) means by deciding whether you’re a good fit. These “That’s not what I expected” situations aren’t necessarily inconvenient only for the man—the woman is bound to find them troublesome too. Personally, I’m more curious about why you’re so insistent on a monthly arrangement. Since a pay-per-meeting arrangement means settling up each time, I think it’s similar to his policy of paying out of his own pocket rather than going into debt.

Sorry, but I found the last part a little difficult to understand. When someone says, “Please date me,” they may simply mean, “Let’s try having an adult relationship once.” The first few months after your first adult relationship are essentially a trial period. I think the idea is to use that time to get a sense of what the other person is like. Of course, their personality matters, but compatibility in an adult relationship probably plays a role too. Once a certain amount of time has passed and you’ve come to trust them to some extent, you can decide whether to move to a monthly arrangement. Monthly arrangements often lead to trouble, so many people—both men and women—are cautious about them.