I’m a male member in my late 40s.

Maezawa from the CEO’s Office here. It’s a tricky question, but I think it would be fine to ask her about the future on the second date. As for how to bring it up… Wait, isn’t this basically the same as a regular date? When you were trying to win over a woman you liked without money being involved, what did you do? I feel like you just need to do the same thing here. The only difference is that an allowance is part of the arrangement. Once you look at it that way, you’ve probably already started picturing what kind of restaurant to choose and what to do after dinner, right? The usual pattern would be: Have dinner at a nice, atmospheric restaurant. Move to somewhere with a beautiful night view. Talk while enjoying the view together. Since the mood should be right, make a move and go for a kiss. (You’d be talking while looking at the night view in a place where it wouldn’t be unusual for the two of you to become romantic.) If she’s okay with the kiss, there’s a good chance she’ll be receptive to what comes next, so smoothly move to a room. Give her a generous allowance and try to build toward a long-term arrangement from the next meeting onward. Something along those lines, perhaps? P.S. Huh? Am I the only one giving off such a strong old-school vibe? Sorry if times have changed.

I’m Rura, a male member of UC and the new salon. I’m not a female member, so I’m sorry—but I wanted to share a quick thought. It’s definitely difficult to know when to invite a Type B woman somewhere after dinner, isn’t it? In my case, if the atmosphere was especially good, I sometimes invited her on the second date and she accepted. But when I was thinking, “Maybe it’s still a little too soon… I’m not sure,” I would casually bring it up in our emails or LINE messages before meeting, so she could mentally prepare herself. That worked fairly well. Something like: “For our next date, how about lunch at the ○○ Hotel? Also, the rooms there are really nice, so if you’re comfortable with it, I’d like to invite you up to a room as well… Would that be okay with you?” I think that’s more or less how I phrased it… Just keep it natural… (笑) If you agree on it beforehand, things go smoothly on the day. Hope this helps.