This is my first time posting a question.

It sounds like you’ve already reached the conclusion that, “If it’s just dinner, there’s no point in dating an older man who doesn’t give me an allowance.” So is the issue that you don’t want to say this and end things because you receive an allowance when you have an adult relationship (intimate)? But ultimately, if you don’t say it, he won’t understand—and even if you try to soften the wording, I feel like it often still doesn’t get through. With that in mind, it seems best to be direct: “I’m not interested in becoming your girlfriend, and I can’t see you if there’s no allowance.” That said, since you mentioned it happened “after we went overseas together last month,” there’s also a possibility that she was put off by seeing him asleep—without makeup, perhaps—or by his sleep talking or breathing, and has reached the point where she thinks, “I might as well end things,” or “I’d continue seeing him if it were free.”

I wonder how it really was. Maybe she didn’t enjoy the trip? It does sound that way… Maybe she was bored and kept falling asleep—or pretending to sleep? Maybe time just dragged on for her? When a woman goes on a trip and actually enjoys it, I think she naturally wants to go again. She starts asking, “When can we go again?” and wants to go as soon as possible. Since it was a special trip somewhere far away, it shouldn’t have been all about the allowance or an adult relationship (intimate)… if she was genuinely enjoying herself. And from the man’s perspective, if she had enjoyed it that much, he’d probably be so touched that forgetting the allowance wouldn’t even cross his mind. When a trip becomes nothing more than a way to have an adult relationship—or to receive an allowance, from the woman’s perspective—it stops being fun for both sides. Going out or dating would lose its appeal too. He may have already lost much of his desire to see her again… After five years, they must have met 500 or 600 times if they met frequently, or at least 200 or 300 times even if they met less often. If she’s still worrying about the allowance, maybe it’s time to end things. If both sides feel grateful for everything over the years, their trust should continue to deepen. Even when it comes to the allowance, they should be able to talk openly about anything on their minds. If they’ve met much less often, then it’s probably just a transactional relationship where either person could walk away at any time. If one of them is feeling dissatisfied, I think it’s perfectly reasonable to move on.

You end your post with “I’m struggling,” but the first thought that came to mind was, terribly rude though it may be, “Are there any brains left in your head?” And the answer is already in your question: simply tell this dreamy papa (a male supporter), “I have no intention of becoming your girlfriend, and I’m not going to see you without an allowance.” Simple, right? Yet you say that “finding the right way to say it is difficult.” As a fussy ultra-rich woman, I’m tempted to add a little sarcasm: “You can open your legs for some old guy without a second thought. Are you perhaps just a loose woman?” It would at least be more endearing if you had drafted something and asked, “Could you edit this?” Why can’t the questioner communicate her feelings to her papa? Perhaps she has zero brains, but I suspect she doesn’t want to look like the bad guy or risk him blowing up at her. After all that teasing, let me teach you, young lady, the golden rule. When you need to tell someone something difficult, the golden rule is to be prepared to make yourself the bad guy—or to take the backlash when they lash out. Once you’re prepared for that, you can say almost anything. In the questioner’s case, the honest conclusion is: “You old bastard, what the hell are you getting wrong? I’m not giving it away for free. In fact, I’m not even going on a date without an Eiichi or a Yukichi!” The challenge is deciding how much to soften that message. Since I have the opportunity, if I may be so bold, I’ll share my own draft: “Sota (pseudonym), I’m truly grateful to you. I’ve spent five enjoyable years with you, and you’ve given me a considerable allowance in line with my wishes. Thanks to that, not only have I gained valuable experience, but I’ve also been able to accomplish many things with the money you gave me. You’ve always taken my selfishness into consideration. Please let me thank you once again. But you know, I’m having a hard time right now, because I like you. You’re married and will never be mine, and I have absolutely no intention of destroying your family. That’s why seeing you without an allowance would be painful for me. I find myself wondering what I mean to you, Sota. Maybe you think of me as a convenient woman. Mariko (pseudonym) absolutely can’t accept that. So I need to continue receiving an allowance as before, including for dinner dates. That gives me peace of mind and helps me maintain trust in you. I’m writing down my true feelings today because I want us to continue seeing each other. You’re such a kind person, Sota, so I’m sure you’ll understand how I feel. I look forward to hearing from you.” *I assumed this was a question from someone in her teens or twenties, which is why I called her “young lady.” But if the questioner really is in her thirties, as she claims, then she’s not exactly a young lady anymore. I do think your thirties are still plenty young—about lunchtime in the course of life—but asking a question like this makes me want to say, “What were you doing all morning?” Afternoon is the prime of life. Pull yourself together.

Maybe he’s been cutting back for a while because his overseas trip cost him a lot. You may both be getting tired of the relationship. After five years, things may have become routine for him too. It might be more fun to end it and look for someone else.

“If he’s stopped giving you an allowance for dates without an adult relationship (intimacy), that means he still gives you an allowance when there is one, right? Then I don’t think he sees you as his girlfriend. From now on, why not stick to dates with an adult relationship (and an allowance)? There must have been some kind of exchange regarding the overseas trip that led to a misunderstanding.”

You could simply say, “If there’s no allowance, I can’t see you again.” If you’re planning to end things unless you receive an allowance, I think it’s best to be upfront about it. I’ve also misunderstood things in a genuine-romantic-feelings papa-katsu situation before, lol, so I can’t exactly speak from a superior position. But men are surprisingly simple, so make sure you communicate clearly enough that there’s no misunderstanding. Fuu also doesn’t believe in paying an allowance for dinner only (no intimacy). After all, if you’re just buying dinner, you can spend time with a young, cute girl. Really, when you didn’t receive an allowance the first time, you should have asked, “Is there no allowance?” If you explain how you feel, I think you’ll receive an allowance if your papa (a male supporter) doesn’t want to lose you. Men aren’t as good as women at picking up on unspoken feelings, so be as direct as possible.

You’re over 30, so I have to wonder whether it’s really okay that you can’t think things through for yourself like this. Even if you ask a complete stranger what someone else is thinking, there’s no way they could know. Also, the exact meaning of words varies slightly from person to person. What you mean by “girlfriend” may be different from what someone else means by it. This is something you should probably have understood by the time you were in middle or high school. I think you should recognize how inadequate it is that you don’t have the ability to tell someone, right then and there, that you want an allowance. If you’re over 30 and still can’t do that, then at least learn some practical life skills—such as keeping your distance from people who don’t meet your expectations. Adding this after reading Mac and Joe’s answers: “An easy woman to take advantage of” is also something people interpret differently. I believe that by giving my dating partner an allowance, I’m asking her to remain someone who’s convenient for me.