I’ve been a male member for two and a half years, and I’d like to hear everyone’s opinions on women’s clothing. I don’t wear suits myself, but usually go for a casual jacket-and-trousers style. She isn’t very particular about her clothes, unlike the women I’ve met before, and when we’re standing together, I can’t help feeling that something looks off. I suppose some people might point out that there’s already plenty of awkwardness since we’re 30 years apart, though.

Unnaturalness isn’t caused by clothing alone—body shape, facial wrinkles, hair color (including gray hair), and other factors can also play a role. If it bothers you, I think you’ll need to pay attention to your overall appearance. Your partner’s sense of style and personal preferences will probably affect things, too. At the end of the day, this is papa-katsu (compensated dating in Japan), so your options are either not to worry about it or to make an all-around effort and choose someone you feel comfortable with.

It would be the worst if she puts effort into her fashion while you, the person asking, don’t care about yours. But if you pay attention to your own appearance, I don’t see a problem.

What on earth is that woman wearing? I usually wear dresses, since I’ve always liked them. I try to dress in a way that won’t embarrass me wherever I go. If you’re involved in this kind of activity, shouldn’t you make an effort to dress in a way that won’t embarrass the man you’re with? So if you really like her, why not suggest something like, “I’d like to go to a slightly nicer restaurant—do you have a tasteful dress? If not, why don’t we look for one together, either by going shopping or browsing online?”

First of all, just walking around together already looks so out of place, so I don’t think you need to worry about it that much. You probably haven’t noticed that people are pointing fingers at you. If you’re going somewhere nice without bringing a woman who suits the occasion, you’re only going to embarrass yourself. Actually, you could just walk around as if she were your daughter. Have her call you “Dad” or “Papa.”

The clothes she naturally comes dressed in are important too. It might be a good idea to play “Pretty Woman” once or twice. Watch the clothes she chooses, and see whether she picks outfits that you can also feel happy about and enjoy seeing her wear. Unlike in the past, women’s clothes are especially affordable now, so even putting together a complete outfit from head to toe—including shoes—doesn’t cost a fortune. You can also find stylish clothes at reasonably priced brands like GU. Even if a man doesn’t have a great sense of fashion, he can still tell whether something suits a woman, and that can help build a small sense of connection and trust between you. In the end, I think you should judge whether she chooses clothes that make you happy. No matter how much you like her, you don’t have to compromise on something like that. If you still want to continue seeing her even though she’s indifferent to her clothes, you could choose activities where that doesn’t matter, such as massages, spas, karaoke, movies, Disneyland, Universal Studios Japan, hiking, drive-throughs, fruit picking, fishing, swimming pools, and so on. P.S. I’ve never done this with a woman from a dating club, but with women I’ve dated normally, since there wasn’t any exchange of money, I would give them a wallet for their birthday or an anniversary. They were already very happy with just that, but as a surprise, I’d put a bundle of 100 bills inside and give it to them, saying, “Let’s play Pretty Woman. You can spend as much as you like.” We’d go shopping for shoes and clothes from head to toe that day. Maybe because they weren’t used to that kind of spending, they would still have quite a lot left over—more than expected. When I handed it back to them and said, “Hold on to this,” they would say, “Let’s use it to have fun next time.” But then they’d return it, saying, “It’s scary having this much money,” and ask me to keep it after all. When shopping, even if there’s a large age gap, store staff are used to dealing with male customers who accompany women. They’ll naturally guide you to a chair while she changes and position you so you can see how the clothes look on her. If you just act naturally, everything goes smoothly. While she’s changing in the fitting room, you can look for clothes you like, or if you feel uncomfortable waiting in the store, you can make work calls or take care of other things on your phone. If you behave naturally, she may even ask you to come into the changing room for advice. In particular, when she’s trying on underwear, revealing clothes, or pants, there may be times when you look from inside the curtained area. With that kind of flow, I think it’s extremely important that the clothes she chooses are things you’re genuinely happy to see her wear. I think it’s also very important for both men and women not to compromise when it comes to the everyday clothes the other person normally wears.

I think it would be good to distinguish between the woman you take to places with a dress code and the one you take to more casual restaurants. Then, if the conversation happens to turn to things like, “I went to a place like this,” or “I’d love to go there with you,” you could say something like, “Maybe when you’re able to dress a little more elegantly,” and encourage her to want to change herself. If she gets into the idea, I think it would be nice to buy her a complete outfit. And if she doesn’t particularly want to change, you can simply continue going with another, more sophisticated companion. Marika

You’ve seen Pretty Woman, right? I feel like that approach could work too. I’m not sure how much it would cost, but wouldn’t a total of a few million yen be enough? It also seems kind of classy to take her shopping and then say, “I’ll leave the rest to you.”

With a 30-year age gap, there’s bound to be some mismatch in the way you dress, no matter what you wear. But you do like her, right? You don’t want to end the relationship. In that case, I’d suggest saying something like, “I’d like to go to a place like this next time, but they have a dress code. Would you mind helping me pick out an outfit beforehand?” and then going to a department store together. That said, there’s a risk she’ll think, “Mind your own business!” and end up disliking you. Many women have strong preferences when it comes to fashion, so she’s more likely to find it a hassle that you bought her clothes she doesn’t like than to be genuinely pleased. So perhaps you should give up on seeing this woman and, from next time onward, make offers to women around 10–15 years younger or older than you.

I basically agree with Mac’s opinion too, but there are a few points I think you should be mindful of, so I’d like to add my thoughts. --- ・First, make sure to compliment her current style as well. If you only criticize it, you may end up hurting her feelings… ・Show her photos of the kind of outfits you like. I think having specific examples will make things easier to understand! ・Start by offering to get her a complete outfit from head to toe, then ask which she would prefer: 【going shopping together or providing support to cover the cost】. ・If you go shopping together, be considerate of the store staff and other customers around you. If the situation feels awkward, be flexible—such as waiting outside! ※Men tend to stand out in stores more than they realize (汗) ・As a guide for choosing clothes that suit her better, I recommend a department store shopping-assistance service or personal styling consultation. You can find options for under ¥10,000, and it may help her get a better idea of how to choose outfits for herself. ・Once she has settled on a particular style, compliment her again by saying, “That suits you even better.” Starting and ending with compliments will leave a good impression! --- I’m sorry for going on at such length, but I hope you’ll take this as my candid perspective as a woman!

That’s one of the reasons I avoid wearing suits. Whenever I see a man in a suit with a young woman dressed casually, I can’t help thinking, “That’s definitely papa-katsu (compensated dating in Japan).” If it bothers you, why not stop offering to women 30 years younger than you, or date women who prefer a more understated style? Rather than asking the other person to change how she dresses, I think it’s better to choose someone whose appearance doesn’t feel out of place with yours.