I’ve only done a few first meetings and dinner-only dates through papa-katsu (compensated dating in Japan) before, but even the people who said they’d give me an allowance for the first meeting never actually paid me.

It depends on whether you’re using Universe Club, an app, or something else. With Universe Club, you receive ¥10,000 for the first dinner, listed as transportation expenses. It used to range from ¥5,000 to ¥10,000, but the rules were revised and it’s now fixed at ¥10,000. With PATOLO, you can set your own transportation allowance anywhere from ¥0 to ¥20,000, so you’ll receive whatever amount you set. If you don’t receive it, you can ask for it yourself. If you’re uncomfortable doing so, you can part ways first and then contact the club to have the staff arrange payment of the transportation allowance. However, Universe Club is only involved in the first dinner. After that, everything is your own responsibility. With an app, you’re responsible from the very beginning, so you’ll have to resolve it yourself. If you agreed on the terms in advance, all you can really do is say, “I haven’t received my allowance.” If they say, “I’ll give it to you all together next time,” there’s a good chance you may never receive it. <Edit> The timestamp on the answer seems incorrect. I suspect the system is using UTC instead of JST for its internal processing.