I’ve been seeing a man in his 50s for about a year. We meet about two or three times a month, and our dates always follow the same pattern: dinner, then a hotel.

Maezawa from the President’s Office here with an answer as well. Thank you for your question. It’s pretty remarkable that, for an entire year, they’ve had the exact same conversations every time—and only about basic things like where they’re from. I think it goes beyond simply not being interested. It’s possible they’re so interested that they keep asking the same questions, but that seems like something an ordinary person wouldn’t do. It sounds like what’s bothering you is the feeling that the other person isn’t interested in you. They may be interested but not know what to talk about, which could be why they keep asking the same things. And I think they invite you out because they are interested in you. So I don’t think you need to overthink it. You can continue seeing them as you have been. You could also try starting a conversation yourself.

I’m Kazu, a male member. Since you seem to be an extraordinary person unlike me, I’m not sure how much this will hit the mark… I think whether someone remembers the details of your conversations and whether they need to have a meal are two separate issues. If eating before going to a hotel isn’t important to them, then over the course of meeting dozens of times, they’d probably try skipping the meal once or twice. For example, as someone who prefers staying in, I usually arrange for room service at the hotel fairly early on. Having room service every time gets boring, so sometimes I’ll buy a bento from the department-store basement and eat it in the hotel room, or go out for a meal after sex. We have all sorts of patterns. Still, when I’m especially worked up, I sometimes find myself wishing I had a partner who would come over at the drop of a hat, without the hassle of dinner. From my perspective, someone who never does that and sticks to the same routine of eating first and then going to the hotel every time is quite an unusual and extraordinary person. Since she seems committed to that routine, asking whether she really needs the time for a meal might be a landmine. So if you’re only mildly exasperated, why not enjoy this as a rare opportunity to observe an extraordinary person? You don’t often get the chance to conduct that kind of ongoing observation while receiving an allowance. That said, I am curious why she asks the same things every time. As an ordinary person, the only dull explanation I can think of is that she’s trying not to mix you up with another partner she’s close to. But surely she wouldn’t confuse details like your siblings, so it is rather strange.

I’m Paper Airplane, a male member. Maybe it feels fresh every time, as if we’re meeting for the first time… This looks like it could last a long time… “Never forget your初心…” Hmm? “Never forget your first medical consultation…”

I’m Taro, a male member. A year of conversations revolving around the same question? That’s not normal. It’s really intriguing. I wonder what kind of expression they have while talking. When they answer a question they’ve been asked countless times again today, do they react as if they’re hearing it for the first time? And if you casually gave them a different answer, I wonder what kind of face they’d make. I think they probably have their own procedure or way of doing things. You probably shouldn’t ask them outright, “Is that really necessary?” They seem like a very unusual person, so I’m sorry, but I can’t answer from their perspective. Still, people like that are rare, so I think you should observe them closely and try to figure out how it all works. That’s a form of affection in its own way, too.