I’ve been thinking about whether I could get back together with the papa I broke up with four months ago. The reason is that I’m struggling financially, but would it be better not to tell him that directly? How should I reach out so he’ll agree to meet me?

I don’t see any problem with it at all. If that papa doesn’t currently have any new women he’s seeing, hearing from someone from his past can be quite welcome. It saves him the cost of making a new offer and gives him something to do. By the way, whether a message is short or long, it’ll be well received when the timing’s right—and not when it isn’t. So try tailoring your message to that papa’s tastes and preferences.

I’m a bit mean-spirited, so let me start by throwing in a little snark. I have to wonder whether it’s really true when someone says, so matter-of-factly, that they “ended things amicably”—that’s not exactly common between a man and woman. Getting back together would presumably give you financial stability, but what benefit would that papa (a male supporter) get from rekindling the relationship? From your wording, it sounds like you’re only thinking about your own circumstances and haven’t considered the other person’s benefits even a tiny bit. Are you willing to accept an offer other than going bare? (If he suggests unprotected sex as a new condition, turn him down immediately. Aside from the risk of STIs, anyone who makes such a ridiculous proposal probably doesn’t actually think the breakup was amicable.)

Start with a seasonal greeting: “Long time no see. How have you been lately? It’s still quite hot out, but I hope you’re doing well and staying healthy.” ↓ No reply → Give up A reply comes ↓ “I’m glad to hear you’re doing well! I’ve finally gotten used to my job, and life has settled down a bit. Lately, I’ve often found myself reminiscing about the fun dates we had. I know this is a selfish request, but would you possibly be able to make time to see me again?” Something like that?

Karasaki from the Universe Club Yokohama branch here. If things ended amicably, he probably hasn’t blocked you on LINE, so why not try reaching out first? If you don’t get a reply, you’ll likely be able to move on as well. You can discuss the details when you meet, but I don’t think any man would take it badly if you simply told him, “I’d like to see you again after all this time.”

I wouldn’t mind hearing from someone I parted with amicably for a good reason, even after a long time. I understand that money is the motivation, so rather than saying too much, you could keep it casual and send something like: “I’ve gotten used to my job and have more free time now, so I’d love to see you again after all this time.”

Thank you for your question. Maezawa here as well. If you parted on good terms and the reason was that you were starting a job, I don’t think you’d have much trouble finding a reason to get back in touch. However, after breaking up with you, he may have started seeing another wonderful woman. If he’s happy with her, it may be difficult for the two of you to get back together. Even if you parted amicably, he may also have been ready to start meeting other women. In that case, he may not have had much lingering attachment, so getting back together would probably be difficult as well. On the other hand, if he still had feelings for you but accepted that there was nothing he could do since you were moving on, he’d probably be happy to hear from you—and the two of you might even rekindle things. So I think it’s worth contacting him, even if you’re not expecting much. You could send something short, like: “It’s been a while. Would you like to meet again on [date] at [time]?” If he’s curious about why, he’ll probably ask. Or, if you think it would be better to talk about it in person, you may be able to simply arrange to meet. Of course, it’s important to suggest a date and time that’s convenient for him. Since you used to see each other, you probably have a good idea of his schedule. I’d suggest giving him about three possible dates to choose from. If he doesn’t reply, you can take that as a sign that it wasn’t meant to be. It’s fine to hold on to the past, but I also think it would be good to look for someone new. Finding a man who’s a good fit overall may not be easy, but I’m sure you’ll find someone. P.S. Kazu wrote that a short message isn’t a good idea, so maybe the Mac approach would be better. Personally, I’d be perfectly fine with a short message, but I guess it depends on the person. ＞＜

It really depends on his personality, the relationship you had, and your former papa’s current circumstances, so it’s hard to say. Personally, I prefer it when someone speaks honestly and directly. I’m disappointed when I’m given a clumsy excuse. That said, quite a few people probably dislike being approached about money. Also, personally, after four months, I’d probably already have gotten close to another woman. In my experience, I usually have someone else by the following month or the month after. Still, there’s nothing to lose by trying. If a girl I’d had a good relationship with contacted me saying, “I got a job, but life is difficult. Would you be willing to support me again?” I probably wouldn’t go back to how things were, but I might consider meeting her about once a month. P.S. Personally, I don’t think a short message or one that specifies a date will work, because it makes me feel like the woman is taking me for granted. If you truly had a good relationship, you wouldn’t have ended things simply because she got a job. So I think ending things on the grounds of getting a job is essentially like saying, “I don’t have any emotional attachment to you.” It probably won’t be easy to overcome that, so I think you should approach him thoughtfully and respectfully.