I’ve been in a papa-katsu (compensated dating in Japan) arrangement with the same woman for a year and a half. We get along well and have good chemistry, so ideally, I’d like to continue seeing her.

I only have one dating partner as well. We’ve been seeing each other for five years. At first, it seemed like she was receiving offers from several men, but none of those arrangements lasted. In the end, I’m the only one she’s continued seeing. We’re more than 40 years apart in age, so it’s not as though we’re seriously in love or anything, but I do care about her. Since you also seem to have only one partner, I think you should set a fixed monthly allowance and treat her well. Before long, you may become the only one she sees, so there’s no need to worry too much. It takes two or three years for an arrangement to become stable, but once it becomes clear that you can maintain a steady relationship, she’ll likely stop accepting other offers. Even though it’s an allowance-based relationship, if you treat her well, she’ll return that consideration in kind. The longer you continue seeing each other, the less likely she is to leave, so all you can do is keep at it while keeping in mind the possibility of eventually parting ways in a way you’re both comfortable with.

Take Aya’s answer at face value. I think young women’s views are pretty much exactly as she described. You need to recognize that being able to have an adult relationship is probably the bare minimum, and if you fall below that, the papa will likely be dropped unless he makes an effort too. My suggestion is that, even if you think you’re taking a risk, you should add one more partner. Seeing multiple people really does spread out your feelings and let you experience a different world. From a man’s perspective too, someone who fixates on just one person makes you think, “She must be having a tough time.” That’s what a dating club makes possible, which is pretty amazing. Why not have relationships with lots of great women? At my age, being fixated on one person and getting jealous would be really uncool, so I always see multiple people. I try to keep things smart and make sure I can maintain wonderful relationships with my partners for a long time.

You were probably obsessed with idols or celebrities when you were a kid. Compared to back then, you’re getting a reasonable amount in return. Interacting with an idol who smiles at everyone might have meant nothing more than a handshake, but now, even if the quality is somewhat lower, you can have as much interaction as you want. Of course, the absolute amount of money you spend is probably higher, but I think it actually makes up a smaller share of your disposable income. Falling genuinely in love with a girl from the club is just an illusion. Just like your passion naturally faded when you were a kid, you’ll get tired of it eventually.

Maezawa here as well. As Mac-san also said, if you want to be with only one person and want your partner to be with only you, then I think you should get married. If you don’t want them to have sex with anyone else, making use of the institution of marriage is the quickest way to achieve that. If your reason is that breaking up would be difficult, then that’s simply selfish. To me, it only qualifies as serious love if you’re prepared to accept that half of your assets might naturally go to your partner if you separate. If you don’t feel that strongly, then I think this is simply about being selfish and wanting to have things your own way. If you want to get your way, offering an allowance of, say, ¥200,000 per meeting would probably gradually reduce the amount of time they spend seeing other people. If even that kind of allowance is impossible, then I think you should reconsider and understand that there are some things in life that simply can’t be had.

You just need to find a woman who’ll do that exclusively for you. My monthly arrangement is over 165 cm tall and has measurements around 90 cm. I guess my particular taste works in my favor.

Ah, yes, yes—happens all the time, haha. First of all, have you told her how you feel now that you’ve fallen for her? If not, you should. If you keep those feelings bottled up, they’ll ferment and become too heavy, so it’s best to tell her as casually as possible while still making it clear that you’re serious. You don’t have to phrase it perfectly. If she completely ignores it, then there’s no chance. Even if she acknowledges it and responds properly, she might say things like, “I’m not really that into you,” or “Of course, if I had to choose between meeting you and someone else, I’d choose you. But I’m doing this because I need the money, too.” There are all kinds of responses, but if she understands your feelings and gives you an honest reply, then you have a real conversation. Once you can have that conversation, various clues and openings will emerge. If you can then try different things and find yourself feeling hopeful one moment and discouraged the next, isn’t that still better than where you are now? People who are naturally romantic can’t simply suppress those feelings, so it’s better to let them out. There are far more women who will give you a proper response than what you see written online. Even answers here sometimes get tons of likes and become mini-viral posts, but they’re completely different from my actual experience. And honestly, I don’t think the date plan, mannerisms, or appearance matter that much either. In the end, you’re getting naked and tangled up together. Within that kind of relationship, women may actually be better than men at reading the other person. That’s how different it is. The almost religious pressure insisting that a young woman could never fall for an older man feels deeply unnatural. I can say that with certainty. Every woman has her own circumstances, and in any situation involving another person, things usually won’t go exactly as you want. Ultimately, the decision is yours: do you end things here, or continue? Ending it and moving on is perfectly valid, but then you won’t be able to see her anymore. If you continue, you may be left brooding, but you can still meet her. Ask yourself which life you’d rather live. In my case, I realized that the deciding factor was our intimate compatibility, and I had my moment of truth: “So in the end, I just wanted to sleep with her.” Since then, I’ve pursued a pretty hardcore dating-club life. My goal is to have great intimate experiences—more romantic play than kinky play. We may genuinely fall for each other and make all kinds of memories, but that’s just the result. That’s more or less how I see it. In any case, nothing will change if you just stand still and worry. If you don’t know what to do, choose your own path and move forward. Even if you reach a dead end, you’ll at least know that path wasn’t right for you—and then you can move on to the next one. I hope your moment of truth comes soon, too. Taro

Additional note: When I give an answer like this, male respondents often complain. Unfortunately, voicing those complaints doesn’t change the reality that most women dislike older men. You could conduct a survey. For example, in June this year, YouTuber Raphael did a vulgar segment in Shibuya asking girls, “How much would you have to pay me to sleep with an older man?” Some ordinary girls answered, “No amount of money would make me do it,” while others agonized over it before saying, “At least ¥100,000 to ¥1 million.” Of course, it was edited to increase views, but the fact remains that Raphael—a popular YouTuber and businessman—portrayed the girls in Shibuya this way. The more important point is that he wasn’t asking whether they could “fall in love,” but whether they could “sleep with” an older man. There are girls who would go to a hotel with an older man for ¥100,000—though even they’re a minority. They can even act friendly. I don’t think this is the best analogy, but nurses are generally kind, right? It’s the same thing. When money is involved from the outset, people naturally act pleasant. So even if a girl might just barely be willing to sleep with an older man, “dating an older man normally” is an extremely high hurdle for young women. It’s like falling in love with someone the same age as their gray-haired father, who lounges around at home unshaven and dressed disgracefully. Of course, there are women who like older men—fewer than one in a hundred, though. Girls who join a dating club already have a certain level of commitment, so some of the respondents here may be benefiting from that. But all that happened is that they made offers to more than a hundred women and happened to come across someone with a father complex or someone a little unusual. Incidentally, I’m also in love with an older man, but people around me say I stand out and that I’m extremely unusual. And there are some attractive older men like my papa (a male supporter)—men with assets worth tens of billions of yen, a strong sense of responsibility toward women, handsome looks, and a good physique. So, if the match happens to work out miraculously, “dating an older man” is possible. Let me say this once again: An ordinary, unkempt middle-aged or older man is not going to be popular with young women. If you want to insist that you’re the exception, go ahead. You get deceived because you refuse to face reality and dream that “I’m the exception!!! Even an older man with wrinkles, sagging skin, and gray hair—who’s moderately wealthy—should be able to have a grand romance with a young girl.” With that in mind, please read the summary at the very bottom of the answer. …………………… “From the conversation, I could tell that the woman was probably seeing several other men besides me…” Based on that, I suspect the questioner isn’t particularly liked. That doesn’t sound like the way she would treat a papa she absolutely didn’t want to lose. In fact, I think she has drawn a fairly clear line between you. Something along the lines of, “Don’t fall seriously in love with me!!” For reference, I also initially met many people on monthly arrangements, but “not unpleasant” wasn’t enough. I narrowed it down to the men who were “really fun to be with” and offered a high allowance. You seem to be worrying about various things, but I think you’ll be happiest keeping your serious feelings inside your heart. There isn’t even one young woman in a hundred who likes men in their late 40s or older. As I also wrote in my previous answer, please read: “Be Careful of papa-katsu Women Who Claim to Like Older Men… ‘There Are No Women in Their Twenties Who Like Old Men!’ — Atsuhiko Nakamura’s Nameless Column” After reading the column, improving your listening skills will help make you more attractive to her. Good luck.

Japan has an institution called marriage for people like the questioner, and both spouses are bound by a duty of fidelity. In other words, the law protects your jealousy and desire for exclusivity. So if you really want a one-on-one relationship, why not try proposing marriage? I’m not being sarcastic. I’m saying this because I genuinely mean it. I assume the questioner isn’t married, but if you are, start by getting divorced. Then we can talk. If you want to monopolize someone without intending to marry them, that’s no different from a child throwing a tantrum. It’s like asking how to make a child who’s crying and screaming in a store because they want a toy give up, right? Try consulting your own inner reason instead of other people.

I think I understand how you feel. This may be a rather predictable answer, but personally, I think there’s no choice but to enjoy this sense of unease and restlessness as one of the charms of papa-katsu (compensated dating in Japan). For me, at least, that’s the best way to deal with it so far. I have one piece of advice—or rather, a suggestion. You seem to feel that asking about other papas would be tactless, but is it really? I’m not saying my way is the right way, but I don’t see it that way. Depending on the relationship and the other person’s personality, I believe it’s okay to ask about anything that concerns you. Of course, you need to be considerate about how you ask, and you also need the composure not to lose your cool if you get an answer you didn’t want. Oh, and since I’m already meddling, let me add this: You seem to recognize yourself as someone who tends to fall in love, but I understand because I’m the same way—and it’s probably a major misconception. Probably, anyway.

The goal is for her to feel: “We have great chemistry and get along well, so I’d love for this to continue for a long time. I’m only seeing this one man, but I sometimes get the feeling that he’s seeing several other women besides me, which makes me feel a little sad.” Some women also have men they feel relaxed and stress-free with whenever they meet. When that happens, they naturally gravitate toward the more comfortable arrangement rather than juggling multiple papas. For example: 1. You meet her whenever she wants to see you. 2. She wants to see you so often that she says she’d be happy to meet every day—and you actually meet every time, even on consecutive days or twice a day. 3. Neither of you feels uncomfortable or overly considerate, no matter how many hours you spend together. I think the key is whether you can build a relationship where you’re able to increase the frequency and intensity of your time together for a certain period. Both women and men can potentially go on dates with four or five people in a day, so unless you meet someone very frequently, it may be difficult to remain their only partner. I also think it’s difficult for both sides to narrow things down to one person if they feel, “I can’t meet that often—it’s exhausting, and I don’t need to.” This was Paper Airplane, who dated the same girl more than 25 times a month for several years…