Mac-san’s advice on how to get a younger man you’re interested in into bed was very helpful. As the reverse scenario, could you share some techniques or personal experiences for winning over a senior female coworker I’m interested in? (Even when I simply invite her to dinner, she turns me down because she has her guard up.)

Mamiya from Universe Tokyo here. Is the senior colleague you’re interested in quite the glamorous, youthful-looking type? I definitely recommend suggesting papa-katsu (compensated dating in Japan) to her. That said, she might be willing to go if you tell her you’ll cover more than ¥20,000 in transportation expenses for dinner with me.

I’m Maezawa from the president’s office, and I’ll answer too. > Even when I casually invite her out for a meal, she keeps her guard up and turns me down. That means she doesn’t like you. (Wait—was I not supposed to answer so directly? Everyone else is being so kind about it（笑）) Still, I think there are ways to go about it. Didn’t Don Juan of Kishu write about this? He wanted to get closer to a flight attendant, but simply handing her his business card didn’t get him a response. So he thought about what he could do... That’s how he came up with the “Don Juan Special.” Apparently, he cut a slit into the back of his business card so he could slip a 10,000-yen bill inside. If the beautiful woman who received the card loved money, Don Juan passed the first screening. If she wasn’t interested, she’d throw away the card—perhaps pocketing the 10,000 yen—and turn the whole thing into a classic funny story to share with her girlfriends, or simply come to hate him and end it there. Isn’t that perfectly fine? The “come to hate him and end it” part makes things clear. There’s no more vague rejection, so you can give up without wondering. That said, I don’t understand why your target this time is someone within your company. Don’t try to keep things close to home. Work on improving yourself and look for opportunities outside the company. With an unbreakable spirit, Don Juan keeps making passes without fearing rejection. Don Juan never hurts the other person’s pride. Even when he relentlessly hit on female nurses at hospitals, he didn’t take things further by groping them. With girls he met at dating cafés, he would listen only to their personal stories, then send them home with some cash—though you could also say he was letting them go because they weren’t his type. (Incidentally, I think her personal story was fabricated.) There are plenty of accounts like this, so perhaps you can use them as a reference.

I’m Marika, a female member. A younger man once won me over by repeatedly telling me, “Marika, you’re seriously cute. You’re exactly my type—an absolute knockout.” He was about ten years younger and not my type at all, but when I said, “Oh, come on. If you’re going to say that much, do you want to go on a date?” he was over the moon. Being able to make such a straightforward move is something you can get away with more easily when you’re younger. If she’s the kind of sophisticated older woman who seems completely out of your league, you’ve got nothing to lose—just go for it. With an invitation like the one above, I feel like there wouldn’t be any hard feelings even if she turned you down. What do you think?

I’m Rin, a female member. Unfortunately, the reason you’re being turned down isn’t that you’re too guarded. That woman sounds kind… I recommend realizing it sooner rather than later and walking away.

I’m a male member who goes by Paper Airplane. My first marriage came from an office romance, but it was so long ago that I’ve forgotten most of the details… If I had to name something that played Cupid, it would be going skiing with a small group. Two friends ended up becoming a couple and got married. Going on group outings like skiing or camping can help, too. There was a time when I used to organize group dates with around 20 or 30 people almost every week. I’d start with friends from work, then have them invite their friends, and before long, people of both sexes were joining casually. That said, being turned down when you invite someone to dinner is pretty tough. Unless you’re particularly handsome, the first invitation is crucial and can make or break things. You need to give her a reason to take an interest in you—for example, getting her to come to you for advice from the very first meeting. Concert tickets could work, or anything she might be interested in, such as investing. At this point, I think you have no choice but to draw her in with something that genuinely catches her interest. P.S. Thinking back, when I got married, a senior female coworker I liked from the same department sent a wedding gift to my home. She was the only person from the company who gave me a present, so it stuck in my memory. I liked her quite a bit, too. We interacted fairly often—mostly with her teasing me—but I never invited her anywhere or asked how she felt. If you work at the same company, you may be able to tell whether a woman likes you or not. As practice, you might try introducing yourself to someone you’ve only met once at a lounge, cabaret club, adult entertainment venue, men’s esthetic salon, or somewhere similar. The important thing isn’t to keep going back, but to make your move in one shot—in that single opportunity. This isn’t about becoming popular; it’s training for not letting the right woman for you slip away. Sometimes, a woman who’s interested will take notice when you open up about yourself. Creating an opportunity to get acquainted is important if you don’t want to miss your chance.

I’m Kazu, a male member. > I imagine myself sneaking around behind my senior coworker’s back and rummaging through her underwear. (⊙_⊙;) Isn’t that probably why your senior coworker won’t even have a meal with you? Work on improving yourself.