When was the last time you broke someone's heart?

It’s been a while, but I broke a friend’s heart fairly early on by letting him know I was heterosexual. Of course, he kind of expected that, and I can’t blame him for trying, so we are still friends.

I don’t think there was any way he could win me. If nothing else, my wife is a better cook :p

Hard to say. What’s the difference between giving someone heartache and breaking their heart? Sometimes, when you get to the end of a relationship, one of you gives up first and calls it over. Does that mean the other person’s heart is broken? Or was yours broken, ages before, and it just kept hurting while you played out the string?

There is only one relationship in my life that I can think of where she loved me more than I loved her, and when I made that clear to her, it broke her heart. That happened 35 years ago. Later, she became a friend.

I don’t think there was anything she could have done to win me. Maybe if I had known what I later learned, I would have been more interested in her. But at the time, I was just coming off a major heart break, and it was a kind of rebound thing. I was in no place to give my heart to someone else. Not that I knew that, but it was true, I think.

My longest relationship. Ten years. I feel out of love with her years before we broke up.

She was ten years older. I eventually grew up, and was no longer interested. I held on so long for various reasons (which I’d rather not mention).

September 2010. Why do you ask?

I don’t know if I ‘broke his heart’ but I definitely hurt him. He wanted a serious romantic relationship and despite him being a lovely guy, he just didn’t do it for me. I only wanted to be friends. I gave in and let things go a little further than that and gave him hope but I then regretted it. I lost a friend. Perhaps, since he didn’t seem to be able to accept friendship was really all I wanted, there was little hope of anything else.

Many, many years ago. He was kind, but I wasn’t interested in a serious relationship. I’d told him so from the very beginning, but he fell in love anyway. As soon as I knew he felt that strongly about me, I broke it off. No sense in hurting him further by continuing a lopsided relationship, you know? He took it very badly, unfortunately.

Probably last year. I had a friend that was just… too attached. He had feelings that I couldn’t reciprocate. One, because they weren’t there, and two, because I am married. I had to end our friendship, which was sad for me, but I know he took it really hard. He wasn’t particularly kind, no. He has an abrasive personality, but I liked him as a friend.
Anything worse than that, like truly cold heartbreaking (that I could have avoided if I were more mature) hasn’t happened since I was a teenager or in my early twenties. I did let a few people down pretty hard, I’ve always had serious commitment issues.

It is a difficult one, because sometimes it has to be done. It is kinder to break a heart and allow it to mend that confuse a heart. I can’t recall the last time I broke someones heart, because I haven’t been looking for a relationship and tell people upfront. Then it is their decision I feel. And any broken hearts I have been aware of, if there were any.

Last year. I’ll never regret breaking up with that boy, he was so needy, annoying, and was also trying to make me be someone I wasn’t. I’m glad I ‘broke his heart’, and I don’t care if that makes me a bad person.

Milo here; It happens so often that I have trouble remembering…probably this morning when my plumber showed up to do some work.

I had to break it to him gently that we could only be friends (unless, of course, he went salmon fishing more often).

In 1962 I know I did. In 1986 I left my marriage (different guy) but I’m not sure I broke his heart because he kept waffling about what he wanted to do. Sniffles over the phone don’t carry much weight with me after what I put up with for two years and I never waffled. I stayed gone. He’s just as crazy now as he was then. I was wondering if he’d change over the years. He found that much younger woman he wanted but it turns out she’s much older than I am physiologically. I’m fine and she carries an oxygen tank around plus she’s a major hoarder. I feel sorry for both of them regardless of how I sound now.

Febuary 9th, 2011. Well, as far as I know.
He was understanding, and very supportive through the whole thing. It broke both of our hearts, but it was something I had to do. We weren’t right for each other, and I couldn’t lead him on.
I think that maybe I’m still breaking his heart. He told me he missed me the other day. I said it back, and he said I didn’t know what he meant. He changed it to “I miss us.” and the conversation went on from there
He’s the only friend I have, and I’m still hurting him. Yet somehow, he wants me in his life anyway.