I’m going on a hotel date with a man I’ve had dinner with once before.

I’m Fuu, a column writer. If four hours is what you prefer, I think it’s fine to let him know in advance, as the other respondents suggested, what time you absolutely need to leave by. I can’t tell what kind of papa (male supporter) he is from this alone, but since he told you upfront that it would be five and a half hours—and even specified it down to the half hour—it sounds like he has planned out a schedule to some extent. At least he gave you advance notice rather than keeping you for a long time without telling you until the day itself, so it seems like he’s being considerate. Personally, if you like your papa and want to continue seeing him, I’d suggest going along with it this time and seeing how it goes. If you find that the timing really doesn’t work for you, you could ask at your next date if you can leave by a certain time.

Maezawa from the CEO’s office here. So you’re saying you can accommodate up to four hours, right? In that case, you could let them know the day before, something like: “I have plans the next day and need to leave early in the morning, so unfortunately we’ll have to wrap things up by 9:30 p.m. I’m sorry. But I’m looking forward to seeing you. Thank you.” You might feel that telling them the day before is a little late, but if you say it several days ahead—or too early—they may suggest choosing a different day instead. If you tell them on the day, they may wonder, “Why are you only mentioning this now?” So I think the day before is just about the right timing. Also, saying that you suddenly ended up having an early-morning commitment the day after tomorrow sounds quite natural.

I’m Kazu, a male member. If she’s only at the point of saying, “I get nervous when we spend a long time together, and I’m worried I won’t be able to make sure you enjoy yourself,” I don’t think it’s time to play this trump card just yet… I think it would be better to tell him that you have to get up early the next morning and would ideally like to head home early. You could simply say that you usually go to bed around 10 or 11 p.m.