What should I do when I start feeling empty about having a financial relationship with a woman, even if it’s a simulated romance?

I’m Saito, a column writer ♪ This time of year feels like that, doesn’t it? For me, January through March also feels like the off-season. Saying it’s not mating season would be rather crude, though. “Feeling empty” might be the same thing as yesterday: a sign of decline. Maybe you joined a dating club because doing the same thing as yesterday started to feel empty. Only you know the real reason. Still, rather than using a dating club, wouldn’t it be better to rely on your usual charm and compete on your own merits? That said, you may be a well-known person, so the risks could be considerable. Finding the right balance really is difficult. I’m stuck in my own routine of emptiness, too. Sometimes, when people have too much money, their conversations and judgment no longer align with mine. Perhaps dating-club members tend to have unusually high incomes—and unusually unconventional judgment. I feel all alone. Spring is just around the corner. Let’s wait and see how things develop.

Maezawa here with my answer. The fact that you’ve already started feeling empty seems to answer the question in itself. At this point, I don’t think you even need to ask here. Why not simply do what feels right to you? It might be different if you felt empty but still couldn’t walk away, though I wonder whether that’s really possible in the first place. If you genuinely enjoy being together, I don’t think the financial side of things would make you feel empty. That’s just how I see it.