I was rejected by a woman I had grown very close to and who had truly saved me. I cared about her too much and did something that violated her dignity, so she completely lost interest in me and refused any further support.

I’m Date◎Yume, a male member. I think repairing the relationship would be extremely difficult. That said, I’m not sure what you mean by “I cared about her too much and ended up doing something that hurt her dignity.” Still, I wonder if, with time, she might remember that you truly cared about her. > Has anyone ever been disliked by a woman and had the relationship end, only to reconnect and become close again? Is it possible? > Even if she’s struggling financially, and no matter how much time has passed, would she really never open her heart again to a man she’s become disillusioned with? I do think it’s possible that a woman who once spent very happy times with you and felt genuinely supported by you might remember that you truly cared about her and forgive you. However, just as you have, I think she may ultimately draw a line under it as a relationship that has ended.

Maezawa from the Corporate Planning Office here as well. > She completely lost interest in me and refused to provide any more support. If things have reached that point, I think repairing the relationship will be difficult. If she simply wasn’t responding, there might still be a very small chance of rebuilding the relationship by giving her some space. But it seems you’ve gone beyond that point. No matter how much you regret it, I don’t think there’s anything you can do now. It may be best to regard it as a learning experience and keep it as one page in your memories. And with the next woman, try not to make the same mistake.

I’m a lost soul in my 60s. So you all realize that this question is from that infamous person, and answer accordingly, right...? P.S. I replaced “woman” with “Mr. Mac” and couldn’t help laughing. You really can’t hide that hopelessly petty, obsessive tone.

I’m Flag Maker, a relationship columnist. It’s hard to answer without knowing what you did to her, but since you’re keeping the specifics private, I’m guessing it was pretty serious. Assuming that’s the case, repairing the relationship may be difficult. That said, if you really want to somehow make things right, people often say—though I’m not sure what the basis is—that the cooling-off period in romance is three months. So why not try contacting her after about three months? Which do you think would have more impact: “I’ve regretted it this whole time. I’m sorry” after a week, or “I’ve kept thinking about it for these past three months, and I’ve regretted it the whole time” after three months? By the way, if something happens and someone stops responding or ignores me, I send them a LINE message just once—after one month, three months, and six months. Actually, there’s one woman like that right now, and it’ll be three months in mid-February, so I’m already looking forward to messaging her, haha. I don’t know how effective it is, but quite often they do get back in touch. I even managed to become friends again with a woman who slapped me, after a year had passed. I’ve also restored a relationship with a woman who had rejected me.

I’m Meg, a female member. You regret what happened, don’t you? I understand how you feel about him. But if it were me, I’d want you not to press the issue any further. You might consider simply sending an honest email or letter expressing what you’re feeling now, such as: “I’m sorry. Thank you for everything. You were my benefactor.” Then all you can do is hope that, with time, he’ll forgive you. P.S. To “Confused Sixties”: N-no way… Am I being fooled again?