I’m the person who asked for advice from the experienced members here before my debut. I followed everyone’s advice to the letter and was happily given the go-ahead to start seeing her. We’ve also arranged to have lunch together for cherry-blossom viewing later on, but would it be better to bring up an adult relationship (intimate) in advance rather than on the day?

You wrote, “I was thankfully given the okay to continue seeing her,” but then asked whether it would be better to bring up “adult dessert” in advance rather than on the day. That part is a little confusing. If you mean that she agreed to continue seeing you for dinner dates only, then there won’t be an adult relationship going forward. Please continue with dinner dates only. If you mean that you’ve simply arranged your next date, then unless you discussed an adult relationship—including the terms and expectations—at that stage, I think it would be difficult to move to an adult relationship on the next date. That said, if you’re okay with the possibility of losing the next date altogether, you could explain the terms of the adult relationship via LINE or another messaging app and ask whether she would be comfortable with them. > What would be a smart way to ask her? If you’re a beginner, I think you should forget about trying to be smooth and make a sincere invitation, treating it as a chance to gain experience. However, many men don’t discuss the allowance when making the offer, and that’s not a good idea. If you already have a specific amount in mind, tell her that amount and be prepared for it to be rejected if it’s too low. If you want to soften the blow a little, you could ask, “What sort of allowance were you thinking?” If she says she’ll accept any amount, assume she means the opposite. Since the allowance also reflects how she evaluates you, negotiating the allowance from that point can become difficult. You probably need to approach it with the mindset that you may have to offer at least 100,000 yen or so. Conversely, once you’re able to do that, I think you’ll be rejected less often. That said, the allowance is only one part of the overall picture. Your personality and character are important too. On the other hand, even if your personality is great, she won’t be able to see you if the allowance is too low. It’s like the front and rear wheels of a car: you can’t drive with only the front wheels, nor with only the rear wheels. Anyone who thinks a front-wheel-drive car can run with only the front wheels should read up on Honda’s history. Honda understood how important the rear wheels were for making front-wheel drive work properly. That’s why Honda had a head start when front-wheel-drive cars first began appearing. (Other manufacturers thought the front wheels were all that mattered, so they couldn’t compete with Honda.)

I think it’s embarrassing to be over 40 and still need everything spelled out for you. If you can’t even manage a relationship with an allowance disadvantage unless someone teaches you every little thing, I have to question you as a working adult.

There are quite a few things I could take issue with, but you call it your “debut match.” As far as I’m concerned, the bell hasn’t even rung yet. “Adult dessert”? Aren’t you underestimating adults? That’s the main event—the real match starts from there, right?? Discussing the allowance and your no-goes is like agreeing on the rules of the match, so keep it clear, concise, and businesslike in writing over LINE. You can play it smooth once the match has started. Save the stylish mood-setting for after the bell rings. “The fun is only just beginning.”

The one thing you have over men her own age is the composure that comes with being an adult. If this is your first time, you may find yourself focusing too much on an adult date. But while she may be interested in the allowance, she may have little interest in or attraction to an adult relationship. That’s why it’s important to make the date enjoyable for both of you. Especially if you really like her, there’s no need to rush into an adult relationship. Treat her with the kind of composure that says you’re fine whenever she’s ready. When things develop naturally, she’ll also be more likely to naturally accept taking things toward an adult relationship involving an allowance. If it turns into a negotiation, it becomes boring and takes the fun out of the relationship for both of you. To earn her trust, it’s also important to let her know that you really like her—so much that you could almost become captivated by her. If she’s happy to hear that and feels reassured, things may naturally lead to a hotel if you hit it off on the second date. And if she doesn’t want an adult relationship every time you meet, things might develop that way around the third, fourth, or fifth meeting. I think it’s fine whether you discuss the allowance beforehand or not. If you can quickly match the relationship style she wants during the first few dates—including how often you meet, for how long, and how often you have an adult relationship—it can develop into a relationship that lasts for years. In other words, she’ll have no reason to end it. P.S. In a dating club, physical compatibility can influence things so much that you could almost say it determines everything. But if you keep trying one person after another in search of the perfect match, you could end up in a cycle where you never find anyone. Don’t forget that. What kind of style suits you? What are you looking for? Do you want both a deep emotional connection and deep physical compatibility, or is one more important to you? You need to figure that out as well. You’ll need a good eye for judging both appearance and physical compatibility.

If it were me, I’d discuss the adult relationship over LINE by the day before we meet: - The allowance - Whether transportation is included or separate I’d only meet after we’ve agreed on everything. The woman also needs time to get ready, after all.