I’m a male member.

I’m Taro, a male member. What exactly did you do in your first reply? lol Simply accepting a letter date doesn’t earn the woman any money. And if it’s through LINE, it takes a fair amount of effort. Once you connect, she’ll keep seeing your profile photo and LINE name, which can feel uncomfortable. So I think she’s sending that first message because she’s looking for an opportunity, even after paying a certain amount in costs. That said, from the woman’s perspective, with a regular offer she’ll meet someone without knowing anything about him, whereas with a letter date, she may find herself oddly judging his value. So I think your chances would improve if you keep in mind: 1) avoiding negative points is more important than scoring points—show that you’re not strange or overly eager; and 2) clearly state that if you meet for dinner only, you’ll cover her transportation. This shows you’re not one of those men who expects a free relationship. There may be a conversation about an allowance, but since you’re not being pushy, the first meeting would just be dinner. Honestly, though, it’s kind of a hassle. So if you feel the same way, I think a regular offer would be better for you.

I’ll answer too—Maezawa from the president’s office. > I understood the risks of letter dating, but… Judging from what you wrote here, I don’t think you understood the risks at all. Did you do any preparation beforehand? It sounds like a beginner starting to invest in stocks without studying anything, then saying after losing money, “I knew there were risks, but the damage was bigger than I expected.” Communicating through writing is more difficult than meeting in person. Your words can be interpreted differently from what you intended, and sometimes even a minor thing can make someone think, “This person isn’t going to work for me.” When you meet in person, you can pick up on the other person’s facial expressions, pauses, and all sorts of other information. If you pay close attention, you may be able to recover from a misstep. But with written communication, you can’t do that. You need to reread your messages repeatedly and proceed extremely carefully, or you’ll fail. You didn’t choose letter dating just to save on the offer fee, did you? I can understand choosing it if you’re confident in your writing skills. But if that’s not the case, you need to realize that the risks are quite significant. In the first place, women don’t receive an allowance of 5,000–10,000 yen just for doing letter dating. If the content isn’t enjoyable, I doubt they’ll feel motivated to reply. I don’t know what the woman is looking for, but you should think of various ways to show consideration and present yourself as a thoughtful man—for example, sending her money via LINE Pay right away. Still, if you truly understand the risks, I think you’d be better off making a regular offer.

I’m Paper Airplane, a male member. The advantage of letter dating is that women can easily tell from the messages and avoid the hassle of meeting in person. So, just give up.

I’m Nana Ayase, a female member. I feel like a letter date lets you get to know the other person better, but I’ve received offers twice myself. Did you start by messaging on LINE? What did you send—did you send a bunch of stickers or something? Or is the woman new and simply inexperienced? There’s far too little information to say anything for sure. That’s a shame.

I’m Kazu, a male member. Of course, I imagine many women would prefer to meet and decide, just as they would with a regular offer. But it seems some women accept these offers out of a sense of obligation to the club. In those cases, you apparently have to capture their interest in the very first email. However, when a message comes across as too eager, it can also make women feel a little put off, so it seems like a real balancing act.