Should the woman be the one to invite him to a second dinner?

I’m Meg, a female member. I always want to see the person I love as many times as possible, even if it’s just for a little while. So when it looks like we won’t be able to meet, I’ll message things like, “I guess I’ll just have to hold out until next month,” or “I’ll have to swallow my tears…” Then he’ll make arrangements so we can meet sooner. To those of you thinking, “Wait, isn’t that a strategy?” I said it purely from the heart, but looking back, maybe it could count as a strategy!? Dear Date◎Yume, Of course, on the days we meet, I’m not thinking, “Oh look, an ATM just walked in!” (*^^*) Oh, come to think of it, I actually do have a nickname for Date◎Yume in my head. Hehe.

I’m だて◎ゆめ, a male member. My situation is almost exactly the same as Paper Airplane’s. In our case, we basically meet every other week each month. When we first met, I asked, “Would you be interested in seeing each other?” She said yes, so I made the proposal. I’d like to see her every day, but we both have work and other commitments, so it’s difficult to find the time. There’s also the balance between disposable and necessary funds—and, of course, I’m an older guy—but neither of us is particularly dissatisfied. I’m not sure whether she sees me as an ATM that came walking in, but she always shows up with a smile (lol). If you didn’t get a chance to bring it up when you first met, why not casually ask, “When can we see each other next?” If she’s your type, I don’t think she’d mind being asked (lol). If she isn’t, though, you might get a “...What?” reaction. Reaching out and feeling out her response could be a good idea, too.

I’m Hikokihai, a male member. Usually, the man is the one who asks to meet again, and after the woman replies that she’ll check and adjust her schedule, the second date is arranged. I also think it’s perfectly fine for the woman to ask, “Would you like to meet again sometime?” In that case, men will generally tell everyone they’d like to meet again, so if he wasn’t particularly interested, his replies may be slow and unenthusiastic. Still, I think it’s worth asking. If you ask, I imagine most men will be more inclined to meet again. Personally, I’d be happy if someone wanted to see me every week, but I think that depends on the man. Someone like me, who has enough free time to sit here writing this, can probably adjust even to frequent dates. But if he’s young and busy, there are probably many men for whom meeting once a month is all they can manage. As for how often to meet, I think most men will respect the woman’s preference. So I think it’s fine to make your desired frequency the starting point for the conversation. After hearing what you want, you’ll probably settle on a frequency that fits within what the man can manage. That’s why I think it’s better to openly discuss how often you’d like to meet. It makes things easier for the man to understand and coordinate as well. And if you’re his top priority, I imagine he’ll make adjustments as much as possible. P.S. Also, if meeting for just one or two hours works for you, it may become much easier to coordinate schedules. You might worry that this means receiving a smaller allowance, but from the man’s perspective, the shorter meeting leaves time for work or other things. He may even give you a little extra, saying, “Sorry it was a short meeting today, but you really helped me out. Thank you!”

Maezawa from the Corporate Planning Office here. > Men, would you be bothered if a woman invited you to dinner every other week? I wouldn’t say it’s a bother, but whether he accepts probably depends on how much he likes the woman. If he likes her reasonably well, he’ll probably accept when she invites him. If he really likes her, he’ll invite her before she gets the chance to ask. Since you won’t know how he feels otherwise, I think it’s worth inviting him more often and seeing how he responds. If he doesn’t accept, it’s possible he isn’t that interested in you—but you won’t know unless you ask. > Should the woman invite him to dinner the second time? I think the man is usually the one who invites her, but when a woman takes the initiative, he may see her as more proactive than expected, which can raise his opinion of her. You have nothing to lose, so go ahead and invite him—just be careful not to come across as pushy.