I'm a man who's just started papa-katsu (compensated dating in Japan).

I’m Tetsu, a male member. You say you plan to go to a hotel every time from now on, but women have a monthly event to deal with. You should think ahead about what you’ll do then—whether to postpone seeing her because of the event, or meet for a meal or something else. Some women don’t want to meet during that time, while others would still like to be asked out on a date. If you handle that poorly, the relationship could even come to an end. If the hotel is going to be the main focus of your arrangement, you may need to gradually upgrade the activities there, or she might get bored (lol). Good luck.

I’m Kazu, a male member. I usually make plans with the intention of going to a hotel, but sometimes we get caught up talking, I’m not in the mood, or the atmosphere just doesn’t feel right, so we don’t end up doing it. For example, this can happen when she starts crying while telling me about a bad experience she had on a first date with another man. I always give her the allowance as soon as we enter the hotel room, so she receives the same amount even if nothing happens.

Maezawa from the President’s Office here. Thanks for your question. I think it depends on the woman. Since this woman had dinner with you twice and went to a hotel on the third date, I’m guessing she may have been a Type B arrangement. If so, there’s a good chance she also wants to enjoy spending time over meals. I’d suggest continuing with dinner plus the hotel for a while, and once you feel you’ve gotten more comfortable with each other, ask whether she prefers having dinner or skipping it. For example, some women are fine with dinner if it’s in a private room, but feel self-conscious about being seen at a regular restaurant. In that case, they might actually prefer going straight to the hotel. The best thing is simply to ask her. Incidentally, I’ve rarely heard women say they dislike going to a hotel every time, so I don’t think you need to worry about that. That said, even just once, you could try to be a gentleman by ending the date after dinner and giving her the same allowance you would have given if you had gone to the hotel. That can leave a strong impression. Even if the allowance is the same as what other men give her, she may come to regard you more highly. (笑) Though I’m sure this is nothing new—experienced men have probably been using this trick for years.

I’m a male member, Paper Airplane. It depends on the woman, but unlike men, I think most women want to enjoy both the meal and the allowance (hotel) every time. Since you’ve already gone on two dinner dates with this woman, she likely leans strongly toward wanting to enjoy dinner and the allowance (hotel) together each time. I also doubt she wants to meet repeatedly for dinner only. So, while adding some variety and enjoyment to the meals each time, if your stamina allows, you could go to a hotel each time up to about once a week. If you meet more often than that, you could make some of the dates dinner only, without a hotel. Even on dinner-only dates, if things get exciting, I think most women will naturally hope for the allowance (from the man’s perspective, going to a hotel). If possible, even at a pace of two or three times a week, I think many women would welcome going to a hotel, since it helps them save money faster. If you go to a hotel every time, she’ll probably want to see you every time as well. But if dinner-only dates happen often enough to leave an impression, I think she may start adjusting the frequency herself.

I’m Marika. It really depends on the person, so I think it’s best to ask what kind of relationship they’re looking for and work out the terms together. Some people may simply want to enjoy meals and drinks, while others may not be happy with a lower allowance if there isn’t an adult relationship (intimate). I hope you’re able to build a good, lasting arrangement!