I’m a male member, and I have a question for anyone—male or female—who has been in a long-term arrangement. As you get more comfortable with each other, I imagine various problems can come up. What specific issues have you experienced? (I’m not asking about problems involving allowances or anything like that.) I’ve been seeing someone a few times now, and it may develop into a long-term arrangement, so I wanted to ask for reference.

I’m Meg, a female member. It feels a bit presumptuous to call it a long-term arrangement when it hasn’t even been a year yet… My papa (a male supporter) stepped on one of my landmines right at the very beginning. Looking back, it’s nostalgic now. After that, he apologized profusely, and here we are today, haha. We still message each other every day without fail. That said, if that suddenly stopped for some reason, I think I’d have to take the hint. The longer you’ve been seeing each other, the more you learn about each other’s routines and lifestyles, so I imagine there are fewer problems. On the other hand, if you’re thinking, “There’s no way I can deal with this person!” you probably don’t want to keep meeting them, and things won’t last very long. Probably.

I’m Flag Maker, a column writer. It’s not exactly a problem, but I have experienced arrangements ending when a woman got married or entered into an adult relationship.

I’m Paper Airplane, a male member. The only relationships I’m continuing are the ones that have become long-term. We’re able to be ourselves around each other, which creates a sense of security and comfort and deepens our trust. Overall, things are very comfortable, with no complaints or problems. People who have only just started their first arrangement are more likely to run into mismatches or communication issues, and when that happens, I don’t continue the relationship. The longer an arrangement lasts, the easier it becomes to express gratitude through thoughtfulness and casually convey how you feel in little ways. I also feel that we’re more often able to be genuinely happy—or even moved—by the small things.

Maezawa from the CEO’s Office here, answering your question. Thank you for reaching out. As a relationship continues, both people gradually get to know each other better, so it seems that problems tend to decrease as well. That said, if the woman is enduring the relationship rather than genuinely enjoying it, the man may think things have developed into a long-term arrangement—only for her to suddenly stop responding.

I’m だて◎ゆめ, a male member. In my case, I’ve only ever been involved with the first woman I dated through the dating club. It’s been about a year and a half now, and I haven’t experienced any real trouble so far. While we’re still seeing each other, I’ve decided not to make offers to other women. It isn’t a problem, but there are so many wonderful women that I sometimes feel tempted to make an offer. Resisting that temptation has actually been good mental training for me（笑） Also, when we first started seeing each other, I was much older—basically an old man—so there was a mismatch between the kind of relationship I wanted and the kind of man the woman was looking for as a papa. She wasn’t particularly enthusiastic and treated it like a part-time job for the money, so we discussed the details of our arrangement several times. After I told her, “If it’s only about the money, go see someone else,” she started taking me and our relationship more seriously, and that’s how things have continued to this day. Now that she receives stable support from me, she seems to see herself as my “contractual mistress”（笑） The more often we meet, the more comfortable we’ve become with each other, and neither of us feels exhausted from the relationship. It feels like an arrangement that benefits us both. I do wonder whether things might become routine in the future, but there are no signs of that at the moment, so I really don’t know. P.S. Another thing I expect may happen is that we’ll end the relationship without any trouble. For now, I plan to continue seeing her until she gets tired of me, but I have no idea when that might be. I’ve told her, “You can tell me anytime if you want to end things,” but there haven’t been any signs of that at all.