How to Move from Pay-per-Meeting to a Monthly Arrangement

First, I think it’s a good idea to ask about his past experience with long-term arrangements. Bringing it up can also help you understand what he’s thinking. If he’s never had a monthly arrangement before, make sure you discuss everything clearly in advance, or things may turn out differently from what you expected. The biggest potential source of conflict is probably how to handle months when you can’t meet due to illness or other reasons.

“I really like you and would like us to see each other long-term, so I’d prefer a monthly arrangement.” Wouldn’t that be enough? If he starts going on about all sorts of financial reasons, I feel like it would kind of kill the mood.

I’ve tried to recall some patterns: - On our third meeting, my papa said, “If we’re going to meet about ○ times a month from now on, would it be okay if I transferred you ○○ yen?” - I had been meeting a papa pay-per-meeting at least three times a month for a year. During the first wave of COVID, when we couldn’t meet for a while, he sent me money anyway, and it turned into a monthly arrangement. - We continued going on regular dates (with no adult relationship) without even receiving transportation money → he started buying me clothes, bags, a phone, a computer, cosmetics, and so on → at some point, the conversation led to him renting a place for me → then he said, “I’ll give you living expenses too.” Come to think of it, I’ve never once brought up money myself. I remember saying every time, “I don’t need this much,” or “This is too much…” I even tried to give the money back on the spot. At the time, my self-esteem was at rock bottom, so I felt like I was receiving too much. I often said, “I’m not worth being given this much money.” In the end, the papa would say, “Then I’ll decide,” and sometimes the amount just kept increasing. If you’re compatible, things can naturally develop that way without you having to ask, so I don’t think you need to worry.

Once you understand the other person’s financial situation, estimate how much they can afford to spend on the relationship and aim for just under that limit. A man who really likes a woman and wants to keep her to himself—and is willing to put that much money into it—will probably offer a monthly arrangement on his own. Aside from those men, many are only using their discretionary “fun money” for papa-katsu. Take as much as you can, but stay just within what they can afford. If you push them too far and leave them overextended, you’ll lose everything.

Rather than focusing on “what you need it for,” it’s more effective to put into words “why you need it.” That way, people can relate to you more easily. Instead of saying, “I need this much for beauty treatments,” try saying things like: “I want to invest in my appearance because I want to make my dream of ○○ a reality.” Or: “I want to keep looking beautiful because I want my papa (a male supporter) to cherish me for a long time.” Sorry, those examples are kind of cheesy. If all you say is, “I need ○○ yen for ○○,” the response might be, “Oh, if you need money, why not ask another papa?” But when you talk about the person you want to become or the dreams you have, they’re more likely to think, “Oh, if it’s to help make your dream come true, I’d be happy to support you.” That’s just how older men are, haha. It’s more effective to inspire empathy than simple understanding. — It’s Me