I recently joined a dating club and, thankfully, received an offer.

Yes, you’re right that formal attire means high-heeled pumps. That said, there’s no need to wear 8- or 10-centimeter heels—or anything like what a hostess might wear. As long as they’re stylish, I think 5 centimeters is perfectly formal enough. You’re not attending a wedding reception, so I don’t think you need to be too particular about it. The man made you an offer knowing your height as well. If it were me, I’d go on the date wearing something that makes me look as attractive as possible. In that case, heels of at least 7.5 centimeters would probably be a must. Marika

Female member Potassium here. No matter what kind of man I’m meeting, I wear high heels. (I bring sneakers for dates that involve going out and walking around.) I want to meet men in an outfit that matches the day’s plans, makes me look my best, and gives me confidence. Men know my height before making an offer, and they should have seen photos of me wearing heels, at least. If anything, wouldn’t it be unusual for a man who feels self-conscious about his height to choose a woman without checking her height first? After reading this question, I became more concerned that you don’t even feel confident enough to decide what kind of shoes to wear yourself. There will be many situations where you’ll need to make flexible decisions. I think it’s important to be clear about what you want, so you don’t end up being unable to decide in the moment, go along with something you’re not comfortable with, and later post a question saying, “That was unacceptable—what do you think?” Even papa-katsu (compensated dating in Japan) is still a genuine relationship, and it’s still a date. Wouldn’t you feel happier being seen and complimented when you look your most beautiful? If you click with someone, they may also support you emotionally. But if you can’t first clarify what you want, I don’t think you’ll find a man who’s truly compatible and willing to support you long-term... If you continued the relationship thinking, “The terms aren’t great, but I’ll keep him as a backup,” then you were also the one who decided that you could suppress your feelings for the money. Rather than complaining endlessly, I think it’s important to take responsibility for your own decisions and face them honestly. And that decision is probably much harder than choosing shoes. I hope you meet a good man. If you’re going to wear heels you aren’t used to, it would be a good idea to bring hydrocolloid bandages, like Band-Aid Hydro Seal, in case you have to walk around and get blisters or chafing. That’s just my opinion. > I met papa wearing high heels, and once we had gotten close, I told him, “When I wear heels, our heights end up being pretty similar... But I want to walk beside papa looking beautiful, so I wear them anyway.” He probably replied, “I like beautiful Potatchan, so heels are fine. Just don’t push yourself when we have to walk a lot.” He’s seriously such a great papa. ※He might not remember, but he messaged me earlier saying he did remember, so apparently he hadn’t forgotten. Sorry for assuming you had!

> Embarrassingly, I haven’t really been to many upscale restaurants. That doesn’t necessarily mean you’ll be going to an upscale restaurant. You haven’t been told the name of the restaurant when you received the offer, right? In that case, you might be taken somewhere inexpensive, so you should go prepared for the possibility that it could even be a gyudon restaurant. Of course, a man who takes you to a gyudon restaurant or family restaurant from the very first meeting is probably not someone whose future relationship with you will meet your expectations. So if he invites you again but you feel this arrangement won’t work for you, or if the allowance is lower than you hoped, it’s perfectly fine to turn him down. Basically, you should assume that the chances of your allowance increasing later are lower than your chances of winning the lottery. What matters is whether, all things considered, you’d like to continue seeing him. If it seems a little difficult, don’t force yourself—just decline. If you feel there’s even something you like about him, you can try seeing him for a while. I hope you’ll make the decision that won’t leave you regretting it. > I was planning to wear high heels as a matter of etiquette, but then I realized they would make me slightly taller than him. It’s possible he made you an offer because he was attracted to your figure. If so, I think high heels that make you look even more elegant would be the better choice. However, some men may make you walk quite long distances, so I think you should choose heels that flatter your figure while still being comfortable enough to walk in for a reasonable amount of time.

Are high heels really required by etiquette? I don’t remember any such rule. So does that mean grandmothers and elementary school children should wear heels too? Of course not. Some men wear sneakers as well. Low heels are perfectly fine. As long as you’re not wearing sweatpants or denim, you should be fine. I’d also avoid knits that shed fibers, since they could end up in the food. If you search online, you’ll find the proper etiquette. Please check it once.

Since they’re presumably making offers based on your profile, you probably don’t need to worry too much about wearing high heels as long as you’re dressed appropriately.

Either is fine with me. I don’t judge the woman I’m meeting based on the height of her heels. If you want to play it safe, I’d suggest going with mid heels.

If a man is already offering to meet a tall woman, then he clearly prefers taller women. So I don’t think he’ll mind if you wear heels and end up taller than him. That said, you may not be going to a high-end restaurant on your first date, so wearing very high heels could leave you feeling uncomfortable if you end up having to walk a lot.

Honestly, I’d prefer a girl who isn’t too familiar with papa-katsu (compensated dating in Japan) and doesn’t approach it with a lot of calculation. But you, the questioner, come across as almost a seasoned pro, trying to calculate everything, with none of that naturalness. In your previous question, you seemed so experienced that I didn’t even feel motivated to answer. From a man’s perspective, even if the allowance is the same, it’s really off-putting when the woman brings it up first. At that point, I lose any desire to continue seeing her. Ideally, she’d either be inexperienced enough that she never brings up the subject—or even thinks to—or she’d be so popular that she already knows exactly how to handle it. Either way leaves a better impression. No man is going to insist on something like height, which can’t be changed. And if he does, you’re better off not forcing yourself to see him. Wear shoes and clothes that let your own natural charm come through. If all you do is calculate the allowance and continue having relationships where you never truly open up, you may end up constantly receiving offers and endlessly struggling with stress. A junior-high, elementary-school, or kindergarten girl who’s ten or twenty years younger than you can say whatever she wants, and—assuming kids these days even have less calculation behind their words—she seems innocent and cute because of that. What’s cute about a papa-katsu girl who can’t even say what she really thinks? Don’t turn this into a business or a service industry all on your own. I want women to remain expressive in their joy, anger, sorrow, and pleasure no matter how old they get—to captivate and entrance men.

I think high heels would be the way to go, Momoko. If they’re around 5–7 cm, the guy has probably already factored that in. And since you’re not exactly going to be comparing heights, whether you go slightly over or under that range probably isn’t important. Height is something you mainly notice from the difference in eye level, so three categories are enough: “shorter,” “about the same height,” or “wow!” By “wow,” I mean that peculiar mix of positive embarrassment and excitement you feel when you realize you’ve become one half of those couples you sometimes see at upscale restaurants: a tall, beautiful woman and a short, bald, overweight older guy who looks like he has plenty of money. In that situation, I’d encourage the woman to go all out in pursuing her own beauty without worrying about matching the man. Men like that have nerves of steel, so it won’t be a problem. And from the spectators’ point of view, the striking contrast is much more satisfying—it gives everyone something to laugh and talk about over drinks at the after-party. Getting back to your question, I think a man would already be expecting roughly that height difference, so you should wear the high heels. First impressions on a first date are pretty important. If he thinks, “This isn’t what I expected,” there may not be a next date. Worse, the entire date could end up feeling like a meaningless formality. On the other hand, if he thinks, “She’s incredibly beautiful—but she might be a little taller than me,” then you’re already inside the penalty area. If, at the right moment, you casually suggest something like, “Should I wear lower heels next time?” you’ll score a perfect goal and be practically guaranteed to land an ideal supporter. Isn’t it obvious which approach is better from the very first move? Good luck, and I’m rooting for you. Taro