I’m a middle-aged female member who joined this year. I’m a Type B (though probably closer to C), and while the offers I’ve received have been extremely few, I’m grateful for them. Lately, I’ve really enjoyed reading the questions here.

Sorry for the long post. Recently, someone I was involved with several years ago suddenly contacted me through Instagram. We had dinner, and he asked me to get back together with him. He’s an elderly but very handsome gentleman. He has an extraordinary amount of vitality—he’s certainly no ordinary person, much like some of the people who answer questions here. So I’d like to ask: ・Would it be okay to tell him that I’d like to receive an allowance from him, which I didn’t receive before? ・I’ve even considered telling him that I’m registered with this club and asking him to join and make me an offer… Or maybe he’s already registered with this club? (His sudden contact and how quickly the subject of an allowance came up made me wonder.) He has a primary wife and a longtime mistress. I learned a great deal about life from him, and it was a very valuable experience. I believe relationships are ultimately a matter of personal values. However, the reason we broke up back then was that, at my request, our relationship also became connected to work, and he became uncomfortable worrying about how it looked to those around him. We also stopped being compatible, including because our desires regarding an adult relationship (intimate) no longer aligned. He told me, “If it’s meant to be, we’ll see each other again,” and I quit my job. Maybe because I want to be seen favorably by others, I can’t bring up money myself. Unless someone is exceptionally considerate, I tend to be unable to refuse people who are pushy and persistent. I can discuss money when it concerns work. But papa-katsu (compensated dating in Japan) isn’t a profession, after all. I joined this club because if I’m going to date a man, I’d prefer an allowance-based relationship. Even in a transactional relationship, though, I’d like there to be at least some genuine affection involved. I’m old enough to have established my own values, and I thought I had learned to make my own decisions. But I cared about this person deeply, and now I’m wavering because I don’t want to repeat the same mistake. I do have a job, but because of family circumstances, my immediate financial situation is also important. Ideally, I’d like to have an allowance-based relationship with someone so wonderful that I wouldn’t even need the allowance. As for my future activities with the club, I intend to make my own decisions and work toward them. I have one more question related to what I mentioned earlier: ・If our past relationship involved him insisting that I not see anyone else—in other words, wanting exclusivity—would making him my papa (a male supporter) this time amount to an “antimonopoly law” violation from his perspective? Since the exclusivity before wasn’t about an allowance, I mean that having an allowance would give us the freedom to maintain a clear boundary. I’m unsure whether I should tell him how I feel, knowing I may lose him. When I think about it alone, I get confused. I’m sorry for asking such a bothersome question, but I would be grateful for your advice.