Regarding Type B

I get the feeling that several important details have been left out of the question, but I’ll give it a shot. First of all, I don’t think anyone would turn down an offer of 15 after being offered 1 for a dinner-only arrangement. That said, she might find it creepy, so you should clearly explain your reasoning. I’m not sure why she turned down the offer of support after telling you about her background, but if she’s the kind of woman who can only feel comfortable receiving something in return for doing something, then you could make the offer together with a reason that fits. For example, the terms for an adult relationship (intimate) casually include “no multiple partners,” but if you offered 15 for a dinner-only arrangement under the same terms, that could serve as the justification. I don’t mean telling her not to eat or have tea with anyone but me; rather, you could say, “I’ll be the only one you have dinner with for money,” or “Please don’t have adult relationships with anyone else.” In other words, you’d be offering an extra 14 in exchange for an exclusive arrangement. You could also give some over-the-top reason like, “I want to be the person closest to you when I see you smiling after working hard to achieve your dreams—teehee.” You could make up a reason so exaggerated that even you’d lose the energy to point out how ridiculous it is. Maybe borrow a line from Weekly Shonen Jump or something. Really, anything works as long as it explains the creepiness—even “I’m just a weird guy.” It’s fine to ask here, but you should also pay close attention to the person you’re dealing with. What wins a woman over differs from woman to woman, and it probably also depends on the context of your interactions after meeting her. The first thing you need to do is analyze all the data from your exchanges after meeting her. No matter how much general advice you get, otherwise it’ll just amount to “throw enough darts and one will hit.” I said at the beginning that important information was missing from the question—that’s what I mean. If you weren’t aware of that, then perhaps that’s the real issue you need to work on. Increase the resolution of your view of life. “From ‘good morning’ to ‘good night.’” Wishing you happiness. Taro