I’m going out to dinner a second time with someone I was introduced to through the club. Would I receive transportation expenses (or an allowance?) in this case as well? Many men on Q&A sites say they lose interest when women bring up money, so I’m not sure whether it’s okay to ask him.

I’m Basil, a male member. In my case, I usually explain at the first meeting that I’m not looking for a dinner-only arrangement, and I discuss the allowance as well. So there are very few cases where the second meeting is dinner only. That said, if she isn’t very proactive but is exactly my type, I’ve occasionally continued with dinner-only dates for a while, sort of as a grace period. In those cases, I gave her the same amount as the transportation money from the first meeting, but I don’t know what other people do when the second meeting is dinner only. It may sound obvious, but if you need the money, make sure to confirm everything beforehand. If you really like her and would rather prioritize continuing even without money, I think you just have to let things unfold naturally.

I’m Date◎Yume, a male member. Since this is your second date, it basically falls into the realm of free dating, so I think it’s something you need to discuss together. In my case, I still gave an allowance even for dinner-only dates. I assume he’ll probably give you an allowance, but if he doesn’t, that might be a sign that there won’t be a next time. It might be worth taking a chance and seeing how he responds. That said, if you want to ask directly, you could say: “Is it okay if we do the next date the same way as last time?” That might be a good way to subtly test the waters. Will he simply think, “Oh, so she’s expecting an allowance for dinner only”? Or might he reply, “I’d be happy if you could spend some time with me after dinner this time（笑）”? Either way, it could be interesting to see how he responds（笑） Thinking through all the possibilities while answering this is exciting and fun for me too!!

Maezawa from the Corporate Planning Office here as well. Since it says the second date is also dinner, I assume the first date was dinner only. In this situation, the man may be hoping for an adult relationship because it’s the second date. So if you ask whether you’ll receive transportation money for the second dinner, he may realize in advance that things won’t go beyond dinner this time, which could leave him feeling a little disappointed. It’s possible that you’re a Type A and that this date was arranged on the understanding that the man is, too. If so, I think it’s fine to ask directly. Since you received ¥10,000 the first time, there’s nothing wrong with asking whether you can receive the same amount again. The issue is when you’re a Type B or C but want to wait until the second date or later before deciding. From the woman’s perspective, it may still feel too early to decide just because it’s the second date. However, men often assume that they’ll have an answer by the second date. That makes it seem difficult to confirm things with the man beforehand. On the other hand, if you don’t confirm anything, some men may mistakenly assume that there’s no need for an allowance because they treated you to dinner. To prevent that, I think you should ask in advance. It’s difficult to know exactly how to word it, but Mac’s message could be interpreted either as referring to the allowance for moving into an adult relationship or as pocket money for dinner only before parting ways, so I think it works well.

In my 30s, and a new member. I think the man is in the wrong if he’s making the woman feel uneasy about the allowance, so I think it’s perfectly fine to ask about it in this situation. It’s a tricky one, haha. Maybe you could ask directly first: “I really struggled with whether to bring this up, but I’m having a hard time covering the cost of ○○… What kind of allowance were you thinking for dinner? (_ _;) I really want to enjoy our date to the fullest♡ I didn’t want to bring it up when we met, so I’m sorry if this makes you uncomfortable m(_ _)m” Then, depending on his reply, you could say something like, “Thank you! I’m really looking forward to meeting you, ○○, so let’s have a fun date♡” If anything, I feel like the thank-you message is more important. It’s hard to think about these things, isn’t it… Realizing that women have worries like this made me reflect on how I should be more considerate and do my best not to make them feel uncomfortable ^^;