I’m a female member, and I have a question about a man canceling the day before.

I’m Saito, a column writer♪. It’s not about the money—I end things when I decide a woman is more trouble than she’s worth. There have been a few times when someone, saying she was short on money, asked, “Could you transfer it to me instead of meeting sometime soon?” Since meeting would have been a hassle, I just sent the money.

I’m a male member, Paper Airplane. I think it’s perfectly fine to say, “I’d like to see you because I need ¥X0,000 by [a certain date].” Whether you’ve met once or two or three times, there’s no problem if the man is considering continuing the arrangement long-term. Even if you’ve only met once or twice, if you’ve been messaging frequently on LINE, there have been times when the girl brought it up herself. You both try to make time to see each other, and that can deepen your relationship as well. As for a bank transfer, I think it’s fine if the man says, “Since I can’t see you, I’ll transfer it to you.” But I personally feel uncomfortable when the woman asks for it directly…though I can’t say for sure without being in that situation. If you’ve met three times, I think it’s okay to ask a little sweetly. It could also be a chance to learn more about each other and clear up anything you weren’t sure about! P.S. If you’ve met three times, he may already have asked whether you need money for anything or if you’re having financial difficulties. His reaction to that might help you predict how he’ll respond. If it were me, after meeting three times, I’d ask whether she had enough money or was struggling financially. I’d also take that into consideration and arrange for us to meet as soon as possible.

Maezawa from the Corporate Planning Office here as well. > Would receiving a message like this make him feel uncomfortable? I don’t think it would be a problem if you’d been seeing each other for a long time, but if you’ve only met three times, I think most men would feel uncomfortable. I’d suggest wording it more like: “I was counting on that money, so I’m in a bit of a bind. Would it be possible for us to meet soon?” That way, you can have the same kind of date as usual and receive your allowance. Also, cancellations due to sudden plans tend to increase around the New Year holidays, so it may be a difficult month.

I’m Date◎Yume, a male member. I think it really comes down to the trust between you and the male member, but since this is only your third time meeting, it may be a little too soon. What do you think? In any case, please take everyone else’s opinions into consideration.

I’m Flag Maker, a columnist. I think it depends on your relationship of trust with the man and on his personal outlook. If you already have a trusting relationship, he’ll probably be willing to accommodate you without any problem. Even if you haven’t built that trust yet, some men may agree if they have the financial flexibility or see it as an investment in the future. That said, some people may not feel good about it when the relationship is still fairly new. Since you’re asking here, I assume you’re feeling uncertain about it. If this is a man you want to stay involved with for a long time, I feel it may be better to refrain from asking. If there’s truly no other option, you should make an effort to help him feel comfortable agreeing—for example, by promising some form of consideration in return (even if you don’t actually follow through, expressing that you intend to), and by showing your gratitude in an especially heartfelt way.