I’ve met someone through a dating club, and we see each other once or twice a month.

You should end things the moment they cancel at the last minute. Men are built tougher than women, so a man might cancel at the last minute once a year—or maybe only once in his lifetime. When I look at my wife, daughter, and girlfriend, they often feel unwell or change plans. But when it comes to papa-katsu (compensated dating in Japan), even women rarely cancel at the last minute.

Negotiating to change something that was already agreed upon usually doesn’t work out. That’s why the first meeting is so important. If you want to negotiate, find your next man first before doing so. By the way, if you’re unhappy with an allowance of 10,000 yen for four hours of dinner and a drive, yet satisfied with 40,000 yen for an adult relationship (intimate), then… Honestly, since you seem to be the transactional type who thinks in terms of an hourly rate, you might be better off presenting yourself as a C or D type. I’ve never canceled at the last minute, but if I did, I’d feel that some extra money should be given as a gesture at the next date. That said, if I felt I was being asked to increase the allowance in the way you describe, I’d probably decide to end things after this date.

If you’re going to keep wondering about it afterward, you probably shouldn’t leave the terms up to him. Besides, you may simply be low on his list of priorities. Meeting only once or twice a month despite the low allowance is already not much, and neither is the fact that he often cancels at the last minute. You make time for the things you want. If he really is busy with work, then he prefers working overtime to seeing you. In the first place, it’s difficult to change terms once they’ve been agreed on. And if you’re low on his list of priorities, it’ll be especially difficult. You could try bringing up a story like some relative suddenly getting sick and needing money, as some Asian women do, and if he takes the bait, you might be able to steer things toward increasing your support. Or you could casually joke, “I’d like a little more,” and see how he reacts. Either way, you’ll probably need a two-step approach: feel him out lightly, and if he shows interest, go in for the catch. You should work on getting some new offers, state your desired amount clearly from the start, and if someone cancels at the last minute, accept it the first time but bring it up if it happens again—basically, train them to treat you properly. Once you have options, you may be able to take a few more risks and negotiate more assertively with the first man as well. Taro

That’s a little too low. It might be a good idea to find another man first, then negotiate. If you don’t negotiate at the first meeting, it becomes pretty difficult to ask for more once things continue beyond the second meeting. In my case, if I cancel at the last minute, I pay double next time. In the first place, I don’t cancel at the last minute even once a year.