I’m new to this. I’ve tried dating apps and similar services because I wanted a partner, but things didn’t work out. So I’m thinking of trying papa-katsu (compensated dating in Japan), since I don’t mind money being involved.

I don’t think jealousy arises when you’re confident that you’re the other person’s number one. It’s not actually that difficult to become the favorite of papas who see multiple women. Many of them end up sabotaging themselves. Simply behaving like a gentleman, not doing anything the other person dislikes, and giving her the proper allowance is enough to put you near the top. Also, you shouldn’t have feelings about wanting a romantic partner. If you’re financially well-off, try meeting her several times a month. As long as you consistently give her the proper allowance, she may come to like you. In the world of papa-katsu (compensated dating in Japan), it’s fine if the woman takes a liking to you and the relationship naturally becomes romantic. But a man asking her to become his girlfriend is inappropriate and honestly a creepy way to think. Personally, I’m not looking for a girlfriend. To avoid becoming unnecessarily close, I see each woman at most about once a month. Even when we part ways, it’s always clean and uncomplicated.

Even in papa-katsu (compensated dating in Japan), there are plenty of men and women who naturally find romantic partners quickly. If you want things to go the way you hope, it’s not just the woman—the papa (a male supporter) also tends to be someone who is generally popular in everyday life. Even when money is involved, generosity and how sincerely your feelings come across can matter more than the actual amount. This becomes even more important when it comes to the relationship itself. Based on what you’ve written, it seems you may feel less anxious by keeping the relationship quite clearly transactional.

Worrying about and feeling anxious over things that haven’t even happened yet is just a waste of time and emotional energy. For now, just give it a try. Then, depending on how it goes, you can make improvements and figure out how to make things work better. Let’s update the mindset that “it’s okay if money is involved.” Whether she’s your wife or your girlfriend, the man usually pays for the dates and may give her money too, right? So rather than thinking of her as a “lover,” think of her as “someone important you’re dating.” With that mindset, you’ll have a better experience, and you won’t feel jealous either. It’s me.

I’m not jealous. As long as you’re trying to sort out your feelings, I think you may actually be clinging to the position of being someone’s one and only partner. If you want that position, I believe you need, at the very least, to be married and have a promise that your partner will support you for the rest of your life. By “at the very least,” I mean that even married men and women may still date someone of the opposite sex besides their spouse. To reasonably expect that kind of commitment, the man would need to die no earlier than the woman—or at least be around her age or younger. Also, when you meet someone through a dating club, you’re starting out with very low expectations that they won’t cheat or get divorced. I also believe you would need to bring enough charm to overcome that, along with the sincerity and actions necessary to earn their trust. In short, I think you need to have earned the right to feel jealous when your partner has other partners. If you want to find someone who will be each other’s one and only, so you won’t have to feel jealous, dating sites and dating clubs are the wrong places to look. You’d be better off going to a marriage agency.