① When should I ask for a higher allowance? ② How can I get him to look presentable enough that I won’t feel embarrassed being seen with him in public?

That’s simply not going to work. End things and look for a new papa (a male supporter). You shouldn’t be seeing a papa whose terms don’t work for you in the first place, so next time, it’s probably best to turn them down from the start.

① He may be kind to you, but he’s just a secondary papa, right? In that case, there’s no need to ask him for a higher allowance, especially since you’re already receiving more from other men. You don’t have to be so focused on getting as much as possible. Try to approach things with a little more composure. The reason he can stay in hotel suites is because his company pays for them. You’re already in your 30s, so I’m sure you understand this, but if you want to maintain a long-term relationship where you’re both valued, it’s better not to nitpick or say too much. As for his appearance, if it’s just nose hair, I think you could simply trim it for him. How would you feel if a man told you to do something about your age spots and wrinkles? I’d think he was being rude.

It’s best to negotiate a higher allowance when you’ve reached the point where you’d be okay with ending things with that man. You should assume that men will almost never be the ones to bring up increasing your allowance. As for grooming, I think what Potassium-san wrote is the best advice. I’ve made socially embarrassing mistakes too, like forgetting to cut the tag off a suit, but when someone points it out, all I feel is gratitude. But if something as minor as age-appropriate facial spots makes you not want me walking beside you, then I simply wouldn’t want to walk beside you either.

I generally don’t negotiate allowances, so I’m sorry I can’t answer that part, but I’ll respond regarding appearance. Based on your question, I think it’s best to be straightforward. A good rule of thumb is to bring up difficult subjects yourself first. For example, you could say, “I’ve been worried about these spots…” or “The other day, I couldn’t bring myself to tell a friend that they had a nose hair showing…” It doesn’t really matter what you say—bringing it up as a topic is probably the first step.

I think it’s fine to bring it up. If he’s a kind-hearted papa, he’ll probably be willing to listen. Trimming your nose hair is a given. If you have the money, I’d buy a wig myself. As for the allowance, it may increase on its own when the timing is right—but if you just wait, it could take years. You could subtly let him know that other people give you ¥100,000, but ask tactfully and be prepared for the possibility that the relationship may end.

① I don’t ask for an increase in my allowance. I don’t think I should. But what does “should” even mean? ② If I’ve built a genuine relationship with someone, then I will bring it up. Here’s why. My understanding is that you believe you’re a woman worth receiving 70,000–100,000 yen from other papas, and that you want to impose that sense of your own value on the man in question this time. While saying that you’re unhappy about receiving only 50,000 yen, what you’re trying to tell this man is: “You’re such a low-level man that I can’t even see you as worth meeting for 50,000 yen.” I honestly can’t understand how you can say that receiving only 50,000 yen makes you sad, yet do the exact same thing to a man without feeling bad about it. That’s why: ① I’ve never asked for an increase. There’s no need to ask. If the man values seeing me more than he currently does, he’ll naturally offer me a higher allowance or do things he feels are worth that amount. The moment you try to make someone else feel the same pain you understand yourself, the relationship has already broken down in that respect. If it were prostitution, maybe that would be fine, since it’s a business. ② As for appearance, I don’t point things out because I want the man to look good for a date with me. I point things out so he can avoid embarrassing consequences for himself. This applies not only to papas. If my boss had his fly left open or a white tag sticking out of his suit’s back pocket, I’d discreetly let him know. It might be embarrassing in the moment, but I’d especially tell someone who I think would find it even more painful to remain embarrassed all day. (I understand the personalities of the people around me, which is why I’d tell them whether they were my boss or my papa.) The papa I’m seeing makes an effort with his grooming and maintains his figure because he wants to walk beside me and knows how hard I work. I believe that’s because he himself naturally places more value on me than I even ask for, without me having to demand that he recognize my worth. When someone doesn’t understand your feelings, I don’t think the problem is necessarily their behavior. First, it may be that something is lacking in you yourself. If you work hard but feel frustrated because your efforts aren’t getting through to the other person, I see that as either a lack of effort on my part or simply a mismatch in chemistry. Isn’t a wonderful, long-lasting relationship one where both people broaden their perspectives, become kinder, and grow together as human beings? That’s just my personal opinion. I’m not so exceptional that I could impose the value I place on myself onto a man who offered to see me and still expect the relationship to continue. So the questioner may not understand what I’m saying, but I honestly feel sorry for the man she’s seeing. I mean, she expects to be valued in a fairly ordinary way when it comes to money, but she isn’t earning that much herself through a regular job, right? By society’s usual standards, that valuation is excessive. So, honestly, papa-katsu women who complain about the money are just overly self-important in the first place. That’s what I thought. Just my opinion, just my opinion. Knock on wood.

I think if you want to ask for a higher allowance, you should simply bring it up when you feel the time is right. I don’t know whether you should wait for the man to make the offer. If you can’t predict how your partner will react, there’s no way I, a complete stranger, could predict it either. In my case, if a woman asks only for an increase in her allowance, I end the relationship. If she asked, “I’d like you to increase the allowance for each meeting. What would I need to do for you to raise it?” then I would probably be willing to discuss it. I’ve never personally wanted to increase the allowance on a pay-per-meeting basis. As I mentioned earlier, if a woman tells me she needs money for some reason, I’m willing to hear her out. But I don’t think I would be the one to suggest increasing the allowance per meeting. Even when I say I’m willing to discuss it, that only applies to someone I’m emotionally invested in and see several times a month. If I only see her once every few months, there’s no room for discussion. Seeing someone once every few months means the relationship is even more distant than the one you’d have with a familiar sex worker. This is only how I see things, so that man might casually agree if you asked him to increase your allowance. That’s why I don’t think there’s much point in asking a complete stranger about it. As for pointing out something about the other person’s appearance, I don’t think that’s a good idea. Something like nose hair would be easy enough to fix, but if his hair is thinning, are you expecting him to wear a wig? If you don’t want to walk around together, I think you could simply act like a woman who is desperate to have sex, meet him in a hotel room, and go straight to bed with him. There is a risk that a man who wants a pseudo-romantic date may lose interest, but it would probably be less likely to offend him than criticizing his appearance.