I’ve met this papa four times, and so far we’ve only had dinner. He gave me some delicious sweets and messaged, “I’ll look for something you’ll enjoy next time, too.”

I’m Dai, a male member. After only about four dates, making a high-value request seems risky. And when you make a request, you should look the other person in the eye. Telling them by message feels very typical of young people these days, but as someone from the older generation, I just can’t relate to it. A woman who knows how to handle things would probably casually mention during dinner that her key case broke, then drop hints about the one she has her eye on from Amazon or somewhere as a way of planting the seed. Though I could be wrong.

I’m Taro, a male member. I think there are two types of men like that. One enjoys the relationship itself, while the other ultimately has getting intimate as his goal. If he’s the former, the relationship will basically continue as before. He probably has his own budget in mind, so if your requests stay within a range not too different from what he’s been spending, he’ll likely welcome them—you get to share a little emotional connection and have fun while staying within his budget. But the moment you start asking for more than that, he’ll probably begin looking for an opportunity to cut things off, even if he responds with a smile on the surface. In that sense, making requests is quite a decisive move. If he’s the latter, and you’re open to that possibility, you might as well use it as leverage to raise the price as much as you can. That said, he’ll also have a budget in mind for that kind of relationship, so when making a high request, it’s important to make it seem like a one-time thing. I think you should feel out his budget range through your conversations and aim to settle as close to the upper end as possible. If he’s the latter and you feel that’s something you absolutely can’t do, there’s no happy long-term future here. Assuming it will eventually end, you might as well think about how much you can get out of the arrangement in the meantime. You’ll probably get a feel for it after chewing gum for about an hour. Dinner works too. With dinner, there’s a delicious moment right before things start to go bad, so in a way, it might actually feel more real.

I’m Aya, one of the female members. If you’ve only met for dinner four times, he may still be in the process of becoming a good papa. I don’t think you should ask for too much just yet. That said, if he doesn’t have other girls, he might be willing to hear you out, so you could take a chance and ask. I’d say there’s probably about a 50% chance he’ll be put off by it. If it were me, and he said, “I’ll look for something next time that will make you happy,” I’d say something like, “Yay♡ I’m looking forward to it! But don’t push yourself too hard. By the way, are you not a fan of sweets, ○○? There’s a really good △△ near my place, so if you’d like…” I’d try to find out what he likes and start by giving him something consumable in return. Of course, I wouldn’t give anything to someone who worries about his family finding out or who’s very matter-of-fact. And if the papa is used to going to places like Ginza clubs, I wouldn’t give him anything either, since gifts probably wouldn’t mean much to him. For someone who’s used to receiving gifts, you could try asking, “I heard a new café opened in such-and-such a place. I’d love to go there with you, ○○!” If you already have a good relationship with that papa, this kind of request can bring you even closer. Whether or not you decide to give him something in return, start by putting real thought into what he might enjoy—both gifts and experiences. Asking for a key case can come later.

You know, it really makes me appreciate how powerful old folktales still are. “The Sparrow with the Cut Tongue” and “The Old Man Who Made Dead Trees Blossom” both teach us not to be greedy, don’t they? If you like the sweets, accept them gratefully instead of turning them down. And if they ask what you’d like, just tell them what you want. Marika

I’m Date◎Yume, a male member. > I do like sweets, so I’d be happy to receive them, but I’d also like to be given things that last or that I genuinely need. Why not just send that as an email? Since it sounds like a dinner-only arrangement, I’d be totally fine with it as long as it wasn’t anything too expensive, haha.

I’m Nana Ayase ♡ Say it cutely: “If you eat that much, you’ll turn into a snowman~” What does it mean for a key case to be genuinely damaged, though? When it comes to clothes or accessories, the cost can get quite high, so for you, since you don’t have an adult relationship with him, it might be asking for a bit too much. If you’re okay with being cut off, go ahead and ask. I couldn’t say it myself.