About transportation costs. I feel like the total amount is all that matters, so why separate them? If it gets late, it can be dangerous, and trains may run less frequently, so I think it would be fine to add a little extra in those situations.

“Transportation” refers to the compensation for having a woman come out for a meal. The club rules set it at ¥5,000–¥10,000. Men are free to give women ¥20,000 or ¥30,000—more than ¥10,000—as compensation for dinner only, but women aren’t allowed to ask for more than ¥10,000. It sounds like you’re asking on the assumption that you’ll have an adult relationship with the woman, but at the dinner stage, you don’t know whether she’ll agree to that. So giving her the allowance upfront is only natural. If you don’t want to separate the payments, I suppose you could meet her and give her the allowance for the adult relationship before you even know whether she’ll agree. But that isn’t standard practice, so even if she assumes you gave her extra compensation for dinner and the meeting ends there, you wouldn’t be in a position to complain. If you’re okay with that, why not try giving her the full allowance upfront? I wouldn’t recommend it, but I won’t stop you if that’s what you want to do. If you want to hand it all over after going to a hotel, would you say something like this when discussing the terms of the adult relationship? “It’s ¥50,000, but since the club’s dinner allowance is included, could we make it effectively ¥40,000?”

I believe the most I’ve ever given as transportation money for a first meeting was ¥70,000. We met in a regional city, and since we missed the last train, I added ¥30,000 to the ¥40,000 I had originally planned to give so she could take a taxi home. Because there are idiots who don’t pay anything, the rule is to hand over ¥5,000 or ¥10,000 as soon as you meet. But there’s no upper limit, so I think it’s fine to give as much as you want. For reference, I usually give ¥10,000 for transportation plus ¥20,000 for a two-hour dinner date, for a total of ¥30,000. It’s a hassle, so I just say, “This is for transportation,” and hand over ¥30,000. If she lives nearby, the total is sometimes ¥20,000, but I’ve never given only ¥10,000. *I almost always choose Type A or B, so the first meeting is dinner only.* P.S. I wonder how that guy from the Fukuoka branch—the Todai Med School Type III graduate with ¥200 million in cash—who said ¥10,000 for transportation was too much, is doing. I really liked you, so I hope you’ll come back. If you’re a hospital-employed doctor working in Fukuoka, your annual income should be at most around ¥10 million. So if he has ¥200 million in cash, I wonder if he’s a doctor making a killing through private practice. A doctor with ¥200 million in cash is truly one of the biggest winners.

The club’s standard “transportation fee” is essentially a thank-you for meeting for tea or a meal at the initial first meeting. If someone is coming from far away, I think it’s generally customary to provide an additional transportation allowance.