What kinds of dates have women in their 30s enjoyed (or been happy with)?

It depends on the person, so it’s best to ask her directly.

It’s a bit of a chicken-and-egg situation, but the date a woman enjoys is simply the date that she enjoys. In other words, as Taro-san says, “The important thing is to plan the date while picking up on your partner’s preferences and the flow of the moment.” As I always say, everyone’s tastes are different, and they can vary depending on the occasion. For example, a woman who likes golf will probably enjoy playing golf, while a woman who enjoys scuba diving will likely be happy to go scuba diving. With hobbies, it’s not just about sharing the same interests—the way you enjoy them and the level of experience also matter. Apparently, some women even like the reliable dinner-then-hotel arrangement. I think the best approach is to figure out what she’ll enjoy from your everyday conversations and her reactions.

If I were meeting on a woman’s day off, I’d want to have a date with some real substance—like going to the driving range or playing a round of golf if that’s her hobby. It can also be fun to take a little road trip and go sightseeing. Maybe I’m the only one who thinks younger women would prefer to go straight to a hotel and be allowed to head home early.

I’m not sure you could really call it a date, but if you listen endlessly to a woman gush about her beloved boyfriend, she’ll grow attached to you. She’ll think, “What a relaxed, easygoing person.” You have to get her talking. The more she talks, the more receptive she becomes. Especially if you get her talking about the things, activities, or people she absolutely loves, you’re practically guaranteed to win her over.

We go together to Olive Spa or get an esthetic massage.

With women in their early twenties, you can sometimes take the lead and win them over by running the date according to your own game plan. But once they’re around thirty, they’ve generally established a stronger sense of self, so I feel it’s important to pick up on their preferences and the flow of the interaction, then build the date around that. For a woman who was into gourmet food, I went with her to some ridiculously expensive restaurants she had listed and made sure to look like I was enjoying myself too. Whenever she suddenly said she felt unwell and wanted to leave after dinner, I didn’t try to stop her or get angry. Apparently, she liked that, because around our third meeting she took my hand, and we eventually became intimate. Another woman acted like a good listener but actually loved talking about herself. Even when I was thinking, “That’s completely different from what you said before,” I kept it to myself and listened attentively. I also ignored the fact that she gradually started slipping into a northern Kanto accent. After a daytime date, I drove her to Ueno Station, and while a huge crowd was crossing in front of us at the Shinobazu Exit intersection, she suddenly kissed me goodbye in the car. I thought, “Seriously?” but just went along with it. Then I smiled and waved as she got out of the car. Things gradually got better and better after that. Another woman looked elegant at first glance but was actually extremely passionate. I made sure to please her in every way she responded to, then tried every possible combination, and afterward even treated her to several extra bowls of noodles as follow-up care. She fell into a deep sleep afterward and seemed very satisfied. But her squirting—or rather, her loss of bladder control—gradually became more severe, so I lectured her, saying, “What kind of person urinates on the bedding?” She looked very apologetic, haha. Sorry, I started wanting to make people laugh as I was writing this and went off on a tangent（笑）. What I’m trying to say is that if you want to satisfy a woman around thirty, it may work well to set yourself aside for a while, go with her flow, and design dates that help accelerate it. If you do this with women in their early twenties, they may simply become overly entitled. But women around thirty generally have a solid sense of their own values, for better or worse, so I think you’re more likely to be rewarded if you move according to their rules. Taro

Since the woman who made the offer is in her 30s, she’s naturally busy with all kinds of social and professional commitments, so her time is precious. That means dates tend to be kept short and focused. If she can only meet briefly late at night, I’ll pick her up near her home. If she happens to be near my workplace, I’ll have tea with her—even if it’s only for 20 minutes. If she gets a little free time during the day, I’ll go pick her up near her workplace. People in their 30s are at the most active stage of their lives, both men and women, as they’re really just beginning to build their futures. Time is important, and money is important too. Even if she doesn’t particularly want anything from the relationship, she may still want to stay connected because she’s an adult woman who wants to be seen as someone serious and respectable. I think it’s important to genuinely understand and empathize with all of that. If she feels safe and trusts you, then perhaps anything you do together can be enjoyable. For example, because she’s an adult woman, if she happens to be nearby and wants to meet but says she doesn’t need an allowance, you should respect her wishes to some extent. At the same time, you should also think about what would make her happy. If you stay connected and remain empathetic in everyday life, women in their 30s often deal with considerable pressure and stress from work and society. So when you meet, you may hear things like, “I feel so refreshed,” or “Spending time with you makes my fatigue disappear.” Even the messages they send when they’re looking forward to seeing you can be very heartwarming. It seems important not to betray what a woman is thinking or hoping for. Of course, because of her past experiences, she may also be cautious in many ways. But that can be an opportunity to surprise her in a positive sense. She may already have a fixed image of men and a strong assumption that they’ll only go so far in what they do for her. So if you exceed her expectations and make her say, “Wait, is this really okay?” or “Really?”—even though you can’t know exactly what she’s feeling inside—I think the closeness between you can deepen quickly in both her private life and work life, as well as in many other ways.