Dear Diamond to Living-With-Regret

By Diamond | Aug 25, 2016

Dear Diamond,

About a year ago I abruptly broke up with a boyfriend of two years. He really liked me a lot. I was feeling screwed up about dropping out of college and not knowing where I was heading. I wasn’t used to having a boyfriend, although I always wanted one; I wanted one but I didn’t want one. I like my freedom. I went out with a few guys since, and I realize that I miss my ex. I think I made a big mistake when I broke it off. I want to write him a letter apologizing about breaking it off so suddenly and hurting him. I really want him to know how sorry I am about the whole thing. I’m really hoping that he’ll want to get back together. What more should I do? Should I pursue this or just let it go and live with the consequences of what I did? I don’t know if he’s with someone else by now or not.

- Living With Regret Now


Dear Living With Regret Now,

Which would be worse — regretting that you broke up with him or regretting that you never contacted him? Will you have yet another regret if you don’t call him or write him?

It’s difficult to move on in life without closure. So Diamond says follow your gut and contact him. But understand that there’s a fine line between following up and stalking. You don’t want to be a stalker.

The art of conversation is disappearing in our society so personal communication such as a letter or a phone call is the braver way to go and Diamond encourages you to be courageous about this. Texts and emails don't allow you to tell the tone of someone’s voice.

I had a situation in my mid-twenties where I had broken up with my boyfriend for many of the same reasons you did; I wasn’t sure of the next level, I needed a little space, I was stressed at my job, etc. I needed alone time to figure it all out. I went on a few lame dates, but my heart wasn’t interested in anyone but my old boyfriend. The grass isn’t always greener; it didn’t feel right to break up with my boyfriend. After six months I realized that I had made a terrible mistake. I missed him terribly, and without thinking it through too much, I called him. He let me know that he was trying to move on and wasn’t sure why I called. I told him that I didn’t know either except that I missed him and wanted to check in. I told him that I was sorry that I had hurt him, we chatted a bit, then ended the conversation. At least I talked with him and told him I was sorry that I had hurt him. If he had been with someone else, I would have had to accept the consequences of my actions and move forward in life with a big regret. But that’s not what happened.

About a month later he called me back, asked if he could take me to lunch for my birthday, and the rest is history. That was 40 years ago and we have four baby diamonds from our love.

The same may not happen with you, my dear. But you will resolve something left hanging. Be honest with your ex and with yourself and like it or not you will have an answer.

Keep in mind:

“Hearts have a way of calling when they’ve been true.”

- Kate & Anna McGarrigle

Advice appearing in Dear Diamond is for entertainment only and does not reflect the views of Courier Publications or its editorial boards. This column is not intended to replace the services of medical, financial or legal professionals.

Contact Dear Diamond:

Ask Dear Diamond your question. Diamond responds to all who write in. Participation in Dear Diamond is always anonymous and free.

Snail mail: 91 Camden St., Suite 403, Rockland, ME 04841


If you appreciated reading this news story and want to support local journalism, consider subscribing today.
Call (207) 594-4401 or join online at
Donate directly to keeping quality journalism alive at
Comments (0)
If you wish to comment, please login.
Note: If you signed up using our new subscriber portal, your username is the email address you registered with and your password is in all caps