They’ve introduced me to some really great men, and when they like me, they invite me out again after our dates. However, many of them don’t offer transportation money separately from the allowance for the first meeting, so I find myself wondering how I can bring it up tactfully and receive transportation money on top of the allowance.

As Seattle-san said, from a man’s perspective, I just don’t like leaving the impression that I reduced the allowance on the second meeting. Why not try asking, “I understand that transportation costs and the allowance are separate. Would it be possible to receive the transportation money separately just for the first meeting?” If a woman asked me that, I’d understand and would give it to her separately. That said, while I wouldn’t think she was greedy, I might feel she was being a bit particular, which would make it less likely that things continued beyond the second meeting. Unless there were other positive factors that outweighed that… Don’t you think it would be more beneficial to prioritize building a long-term arrangement rather than placing importance on receiving that one unit for transportation at the first meeting?

I don’t think you’re being greedy. Personally, I give the transportation money as soon as we meet and make it clear that it’s separate from the allowance. I don’t think there’s any way to avoid upsetting someone entirely. If they don’t give you the transportation money right away, perhaps you should avoid expecting it to be separate from the allowance.

I always gave it separately. Under the club’s rules, you give the transportation money as soon as you meet, and after that, things are up to the two of you. If you hit it off, that can lead to an adult relationship (intimate). But if, for example, I offered “7 for an adult relationship” and she agreed, I’d feel that explaining, “Since I already gave you the transportation money, it’s 6,” or simply handing over 6 without saying anything would make me look stingy. Personally, I’d also feel pretty uncool doing that. So I don’t think there’s really a smooth way to bring it up—it comes down to the man’s personality. Of course, men who don’t think the way I do might naturally see it as being too money-focused. But even for a man like me, if the woman brings it up, I might think, “I was going to do that anyway—you didn’t have to say anything. This girl is really money-minded.” I fully understand that she’s doing this for the money, and I don’t think being money-conscious is inherently wrong. But the moment that attitude comes across, it’s usually a disadvantage in this kind of arrangement. I think it comes down to being loved enough that the man enjoys spending money on you—and finding a man who has that kind of generosity in him. The women who can do that are probably gaining a lot from these arrangements.

It may seem a little greedy, but even if there’s no transportation allowance, since you were able to meet for the first time—and it’s a once-in-a-lifetime occasion that will also be your first and last meeting—it wouldn’t be unreasonable to receive something extra, such as a thank-you, celebration gift, or tip, worth more than the transportation costs. That said, someone asking a question like this may be less likely to receive anything.

From the man’s point of view, if you do that only the first time, you might get exposed here, with people saying that you arbitrarily reduced the allowance by ¥10,000 from the second meeting onward. You may need to say from the start that you want ¥60,000 all-inclusive. In my case, I’d give ¥10,000 upfront, then clearly state and negotiate the remaining ¥40,000—¥50,000 total, including transportation.