I’m posting because I’d like to hear your opinions on whether I should end things.

From the wording, it strongly sounds like you have no desire to get married, so I feel like breaking up may be your only option. If you’re finding the woman annoying, start by reducing how often you see her. Another more drastic approach would be to say, “I’m sorry, but I’ve contracted syphilis. You should get tested too,” subtly implying that you’re a scumbag with other partners. If you do that, I’d say there’s about a 40% chance she’ll come to dislike you. If you stop seeing her for a while, your feelings will cool off unless you’re exceptionally compatible. So why not say you’re taking time off for syphilis treatment, avoid meeting for a while, and then keep reducing the frequency by claiming you’re feeling unwell or whatever? Also, since you’re still in your 40s, you probably feel like you’re just barely still popular. But looking at my papas, things seem to change once they hit their 50s. Especially after 55, I’d say. No matter how much you try to fight aging, you grow older year by year and start to give off more of an “old guy” vibe. Dating younger women becomes exponentially more difficult. Aging does add character, but it seems that with each passing year, during sex, you increasingly find yourself thinking, “Huh? It feels like there’s some kind of disconnect between me and these girls… Am I only attractive because of my money? Wait… Is this girl after my money too?” As a result, it becomes increasingly difficult to match with women who are genuinely your type. You may have money and no shortage of partners, but you end up having more relationships that leave you feeling somewhat unfulfilled emotionally. I can say this because, from the outside, I’ve watched papas age and seen the nature of the messages they receive from papa-katsu women and hostesses clearly shift toward being motivated by money. But compared with that, the questioner’s situation is still very comfortable. One day, you’ll probably look back and think, “I was pretty privileged to be worrying about whether to break up with those women.” Until then, continuing to enjoy the messy drama to the fullest is also a perfectly valid option. Fighting!

If you’re worried about growing old alone, you could get married. If you’d rather keep enjoying yourself without worrying about it, you don’t have to. You could marry that woman and continue your club activities, or break up with her and date other women instead. It’s up to you.

I don’t think you necessarily need to break up. For now, I’d suggest stopping the allowance payments. Then you can see how the relationship changes and decide what to do from there. I think you probably already sense this, but the reason you can’t truly fall for her is that she’s saying she wants to marry you because you give her 100,000 yen per pay-per-meeting arrangement—not because of who you really are. You feel that it’s a little separate from the real you, don’t you?

If it were me, I’d continue the relationship but wouldn’t get married. Once you’re married, you can’t fool around with other people. I wonder if 500,000 yen a month is spending a little too much. Why not just continue things as they are? If she doesn’t like it, she’ll leave. Saying you might get married someday would be dishonest, so be upfront that you have no desire to get married. That’s what I was telling myself—someone who’s practically single anyway. P.S. Aya’s answer below is pretty profound. Lately, I’ve really started to feel myself getting older, and I can’t go for women in their twenties anymore. Maybe that’s okay in its own way.

If you’re having doubts, then isn’t breaking up the only real option? It sounds like she’s decided that, at this point in her life, marrying someone who’s easy to be with, reasonably likable, and financially stable is the best choice—especially since finding a new papa-katsu (compensated dating in Japan) partner is becoming difficult, but she can’t get by on her own income. If you don’t feel ready to take responsibility for sharing that person’s life, then the answer seems pretty clear.

Even if you marry someone you believe is your perfect match and feel happy spending the rest of your life with them, a certain percentage of marriages still end in divorce... If you're unsure, I don't think you have to get married, and you don't have to continue things as they are now either. That said, based solely on what you've written, I do feel that trying marriage once might not be a bad idea. Do you really need to break up...?

Get a grip, old man（笑） Even a kid in his twenties should be able to make decisions about his own life. That reminds me of advice I received from a senior colleague in his fifties when I was in my twenties: “Don’t have sex with someone you’re thinking of breaking up with.” If a woman wants to marry you or have children with you, she might poke holes in condoms, claim she’s taking the pill, or even lie and say she’s pregnant. At the time, I thought that was the kind of thing you only saw in manga, but I later learned that quite a few women are willing to take such drastic measures. You’re not some barely twenty-year-old girl, so at least think for yourself about whether you should break up. Also, I don’t think seeing multiple people through a dating club is inherently dishonest.