Toward the end of dinner, when we discussed the terms of the adult relationship (intimate), I asked him to please always use a condom. He gave me an awkward smile and said, “You seem pretty experienced—almost like a pro.” I tried to explain myself, but no matter what I said, he just kept smiling awkwardly. He said he didn’t want someone who was a pro, and since I didn’t understand why he was taking such issue with it, we ended things there.

I’m Maezawa from the CEO’s Office, and I’ll answer as well. Thank you for your question. I think Mac’s example is easy to understand. If you act a little shy and hesitant when bringing it up, and avoid saying “condom” or “rubber,” using a vague term like “that thing” instead, I don’t think you’ll come across as a professional. The key is to make it seem really difficult to say. Men are sensitive, so the slightest thing can make them think, “She must be a professional.” As for the allowance, for example, from the woman’s perspective, if you don’t receive it as soon as you enter the room, there are risks such as: - He later claims he thought it was a transactional relationship with no allowance. - He says he forgot to withdraw money, so you receive only a small amount—or he says he’ll pay next time, but you never see him again. - He says, “This is all I have on me,” and gives you less than agreed. So naturally, you would want to receive it upfront. However, men really dislike being told that. In some cases, they may even suggest that you’re a professional. That leaves you with no choice but to wait until he offers it—in other words, to receive it afterward. Even so, you absolutely need to discuss the allowance clearly beforehand. If possible, you should also take precautions such as recording the conversation.

I’m Kazu, a male member. In my experience—having had adult relationships with around a dozen women—none of them has ever asked whether condoms would be used when discussing the terms. Trying to imagine myself in that man’s position, I think I’d be surprised if a woman brought up condoms, and the first thing that came out of my mouth might be, “You seem pretty experienced.” I don’t think he necessarily meant to be confrontational. It was probably just an ill-considered remark that slipped out because he was surprised, so I’d suggest overlooking it the first time rather than focusing too much on his exact wording. Here’s my answer: How about prefacing it with something like, “The last person I met tried to do it without a condom, so I’m scared and just want to make sure”? That way, the man will be mentally prepared for you to ask about condoms, making it less likely that he’ll be surprised—and less likely that he’ll say something thoughtless. If he still gets heated and starts saying all sorts of things, he probably has no intention of using a condom, so I think it’s best to decline. You might also want to leave some brief feedback so he can’t send you unfair negative feedback first, such as: “When I asked about condom use while discussing the terms of the adult relationship, he made a sarcastic remark.”