Regarding the letter date question I asked earlier, here’s what happened. After the other person greeted me, I replied: “Hello, I’m ○○. Likewise, nice to meet you. Where do you live, △△? I live in ××.” They replied: “Nice to meet you, ○○. I live in □□.” I said: “So you don’t live in [the area mentioned]? I’d like to meet you sometime—where would you prefer to meet? If possible, I’d like somewhere near ◇◇.” They replied: “I prefer □□, so meeting near ◇◇ would be difficult. I’m sorry.” I then said: “In that case, how about somewhere near □□?” After that, they stopped responding. Their profile didn’t limit their preferred area. I’d appreciate any feedback on what I may have done wrong.

I’m a lost man in my 60s. Haha, Mr. Flag Maker! There’s absolutely nothing strange about it‼︎ I honestly don’t understand why, despite the whole point of a letter date, things suddenly turn into, “So, when and where shall we meet?” For me, the fun—and the real appeal—of a letter date is putting our exchanges into words and making the woman think, “I’d really like to meet this man,” before we actually go on an offer date… Even when a woman’s messages are brief, you can pick up on little hints and keep the conversation going—that’s the same way it works when you’re talking on an actual date, isn’t it? There’s a woman I finally got to meet after continuing a letter date for more than six months. Even then, we only had that one dinner date, and we’re still continuing our letter date… lol Maybe I should submit a column about my letter-date experience—not exactly advice, though… hahaha.

I’m Flag Maker, a column writer. Maybe I’m the one with the odd perspective, but wouldn’t it be safest to start with an apology along the lines of: “I really wanted to make a regular offer, but since we’re under a state of emergency, I ended up applying for a letter date instead. I’m sorry.” After all, the woman knows that the amount being paid to meet her is lower than usual. Am I the weird one here? What do you think? lol

I’m a male member, “Paper Airplane.” This exchange gets minus 100 points. It comes across as though you only want to meet her because you’re after her body, so of course the woman would think, “There’s no reason for me to meet him. Goodbye.” With the first exchange, 30 minutes is more than enough to arrange the date for your first meeting. You made an offer to someone you liked, right? You’d be happy to hear back from her, wouldn’t you? Women are there to meet someone and receive an allowance, so even if you casually suggest an appointment, it can be arranged almost immediately—100% of the time, and much faster than asking the staff to set it up. However, unless the woman feels that you’re a good person—a wonderful man who likes her and will treat her well—meeting you is pointless, and so is continuing the conversation. Since everything is in writing, your intentions come across all too clearly. You haven’t conveyed any excitement or interest in her at all. Instead, you keep talking only about what works for you. You seem pushy, unlikely to maintain the relationship, and stingy. She’s probably thinking, “What a nuisance. What a waste of time.” That said, thanks to people like you who are bad at letter dating, women do appreciate it when someone simply communicates smoothly. If you want to find a happy relationship, you should probably recognize your current situation. P.S. As for the meeting place, with letter dating it’s such an unimportant detail that, after a week or a few days have passed, you might only discuss it the day before the date by saying, “Where should we meet tomorrow?” So it’s odd to ask about it as though it were important right from the start. You shouldn’t make an offer to someone who requires that much back-and-forth. And even if you do continue the conversation, the date and time should be decided first. The advantage of letter dating is that you can ask her directly in advance. From there, you can talk about where to go, places she’d like to visit, what she wants to eat or her favorite foods, and places she’d like to try. That’s how it becomes an enjoyable date, and you can decide where to go based on those conversations. There’s no need to decide the meeting place first… With a staff-arranged date, you do need to decide the meeting place, because that’s where it begins. With letter dating, you can decide or change the time and place flexibly on the day itself, and communicate as casually as you would when meeting a friend. In other words, even if nothing else has been decided, it’s fine as long as you’ve first agreed on something like, “Around what time on which day?” or simply, “Around lunchtime on Thursday.” Also, with a staff-arranged date, you ask, “Where do you live?” at the beginning. With letter dating, that should be left until last—or, ideally, asked when you meet. It’s something women generally prefer to keep vague. Women would rather avoid being asked for their phone number or where they live.

Maezawa from the President’s Office here as well. Thank you for your question. I’m not particularly good at writing, to the point that I probably wouldn’t choose a letter date in the first place, so I want to say upfront that what I’m about to write may be completely off base. (Just putting up a bit of a disclaimer. lol) (I deleted my sample message. lol) I think the key points are that you want to enjoy a meal, with the attitude that you can decide what happens afterward once you’ve met, and that, just like with Universe, you’ll still provide an allowance even if you part ways after dinner only. In other words, the stance is: “It’s the same allowance as with Universe—the only difference is that the person making the offer changes from the staff member to me.” I wouldn’t write “5,000–10,000 yen,” because saying “Could it really be only 5,000 yen even though we’re talking here?” feels a little cheap. That’s probably about it. I’m really not good at communicating by email, so I’m not sure whether this is right. I’m the type who finds it easier to meet in person, after all...

I’m Kazu, a male member. Maybe it just became too much of a hassle for her after all. I felt tired just reading it.