It says that if you cancel a date on the day of, you may be charged damages. Does anyone actually get billed for this?

Judging from online legal consultations, there have apparently been actual cases where someone was sued for damages after canceling a papa-katsu (compensated dating in Japan) arrangement. Since this is a civil matter, basically anyone can file a claim. If you ignore it, the other party may take the matter to court. If that happens, you’ll need to submit a written answer. If you neither submit a written answer nor appear in court, you may be treated as having accepted the other party’s claims and could lose by default judgment. If you submit a written answer, I doubt the court would rule that you have to pay damages. However, you probably won’t be able to prepare the written answer without hiring a lawyer, so it would be quite a hassle. In conclusion: Don’t cancel at the last minute. If you have an unavoidable reason to cancel, contact the other person through the club. It’s easier that way, lol. And regardless of papa-katsu, letting someone know when you cancel is simply common courtesy.

“You may be liable for damages” means that you may actually be charged damages. I’m not sure why you’re asking this assuming you won’t be charged, but canceling at the last minute on the day itself is that serious. That said, if you were involved in a traffic accident or something else beyond your control, the police should be able to issue an accident report. If you have documentation like that, it may be considered unavoidable and therefore excusable. However, if you caused an accident but no one was injured, you could still have contacted them to ask whether arriving late would be acceptable, even if it took 30 minutes to deal with the accident. In that case, damages may still be claimed even if you have an accident report. In any case, please don’t cancel at the last minute.

I’ve had someone cancel on me at the last minute once, and I ended up wasting 100% of the money I’d spent on the meal. It’s happened once with a trip, too. Strictly speaking, shouldn’t the person who cancels be responsible for the cancellation fee? People may let it slide because it’s papa-katsu, but if it were a friend, you should properly cover the cost.

If there’s absolutely no such provision, then it probably wouldn’t be written that way. If you do something truly out of line, that possibility may arise. But, for example, I don’t think you’d be asked to pay damages just because you canceled after being involved in a traffic accident.