A Heartbroken Business Owner in His 50s After Breaking Up with a Woman in Her 30s

> What do you think of living this way? That’s stalking. He only thinks about himself, doesn’t understand why they broke up, and isn’t considering how much trouble he’s causing her. I’m more worried about whether the woman has properly consulted the police.

Stop dwelling on it—you’ll just have to move on. Since it would be pitiful, please stop doing things that make you look like a stalker. It’s unbecoming of a grown adult. That said, well… if he’s just a man with money, a loner with no dreams or interests, he probably doesn’t seem very attractive to women. It might not work with Japanese women. Since the questioner’s hopes seem unlikely to come true in Japan, maybe spending your later years somewhere with a lower cost of living, like Bangkok or elsewhere in Thailand, could work out. There are YouTube videos of older men living abroad with young local mistresses, and they look like they’re having fun. There aren’t even any historical dramas to watch, and being far away from Japan might also help the memories gradually fade… What do you think?

The answer from Mac is far more entertaining and interesting than the question itself—it actually makes me want to hear more. Mac, please write a column about your story of losing your virginity at 18. As for the questioner, your writing skills are seriously lacking, so that’s where your training as a man should begin. If you’re going to keep asking questions, at least make it entertaining for us. > What do you think of living this kind of life? If the person themselves is happy with it, then what’s the problem? Comparing yourself to others will only make you unhappy. There will always be someone above you. That said, I do feel envious. I’ve managed to build the beautiful-women circle I used to dream about when I was young, but there’s no room for any new women to join it. My monthly-arrangement partners are simply too young and beautiful. Today, too, I made an offer through Universe Club and had a first meeting. She was incredibly beautiful, but when I compared her with the women already around me, she ranked toward the lower end. I don’t think another woman will ever come along who can break into the beautiful-women circle I get to spend time with and rise to the top. It feels like I’ve reached my limit for growth. In that sense, I’m envious of you, since you still have so much room to grow. Start by looking for a beautiful woman around 29. Then try 27, followed by 25 and 23. After that, you could go back to 30 and even try women in their 40s. There are plenty of women more wonderful than your ex-girlfriend.

Looks like this is turning into a series. All I can say is, do whatever you want. Since you seem likely to get arrested, make sure you properly settle things with your family and people you work with so you don’t cause any trouble for respectable people. Please ask your next question around the time you’ve done that. That might bring out some good answers from the other respondents too. I’m looking forward to it. Thanks for giving us something to entertain ourselves with.

Please enjoy life as a wonderfully clueless guy. I enjoyed Mac-san’s step-by-step story about the 18-year-old girl. It brought back memories of my own student days… The appeal of girls aged 18 to 22 or 23, who still have so many things left to discover, is something each person sees differently.

When you ask me what I think, it’s someone else’s business, so I don’t really have any thoughts on it. I’m just like, “Huh, okay.” At the very least, I’m not envious of that way of life. It reminds me of those middle-aged and older men who got hooked on Philippine hostess clubs years ago, abandoned their wives and children, and moved to the Philippines. If the person involved is happy, then I suppose there’s nothing wrong with it. As for me, today I had my fifth date with an 18-year-old B1 virgin who sent me a reverse offer about a month ago, and I finally had the honor of helping her graduate. I’m so happy. I feel blessed. The reason I’m writing something completely unrelated is that the questioner probably isn’t interested in, or envious of, my story about helping a virgin graduate, right? What makes someone happy differs from person to person. If you ever feel happiness welling up inside you, all you have to do is let yourself go with the flow. That’s all there is to it. There’s no need to ask other people for their opinions. But if the questioner still wants us to listen to their story, then please listen to mine too. That 18-year-old read my answers in this question box and then registered with Universe. She thought, “So there really are men who will be with a virgin.” It probably didn’t necessarily have to be me who helped her graduate, but she searched for me anyway and sent me a message saying, “You seem wonderful.” That made me happy. I’m in a great mood today. Though I’m usually in a pretty good mood anyway. On our first date, we hugged. No kissing. On our second date, we got down to our underwear and hugged. Kissing was still off-limits, and I wasn’t allowed to move her underwear aside to look. On our third date, we kissed. I took off her underwear, confirmed her virginity, and took pictures. On our fourth date, there was oral sex, deep kissing, and one finger. Penetration was still off-limits. On the fifth date—today—she was hesitant at first, but I guided her by putting her on top and saying, “Try lowering yourself slowly.” I got the tip in, then turned her over into the missionary position and inserted about two-thirds. After that, we switched to from behind and I inserted it all the way. After we parted, she sent me a thank-you message: “Thank you for today! I was scared at first, but I’m glad everything worked out. I look forward to seeing you again on the [date].” I replied: “I’m happy and honored to have fulfilled such an important role. I hope we’ll continue this relationship for a long time.” So, what do you think? Has the questioner found this so ridiculous that they’ve lost the will to keep reading? The questioner writing such a long post here is really doing the same kind of thing. Paper Airplane and Loser, thank you for your comments—and excuse me for the little solo comedy routine. This is starting to sound like a column! By the way, this girl has already left the club, so I don’t think she’ll show up in a search. I’m mentioning it so no one mistakes her for someone else and causes them trouble.