Letting Go of the Girl I Broke Up With

Reader’s Question

I’m a 39-year-old male who recently ended a 3.5 year relationship with a woman who was 25. For two years this woman struggled to get into nursing school, which I supported to my own detriment. Once she got in, however, she quit before completing a semester. She had severe ulcerative colitis, and was permitted to take time off and come back, but simply quit altogether. After this, I had a hard time believing in her and supporting her endeavors. She blamed her decision on her health.

This woman broke up with me over the phone after I’d taken her family out for Mother’s Day. She continued to struggle with her illness. We eventually hooked up again. She switched her career plans several more times and seemed to be unable to commit to anything. She told me I expected too much of her, but I just wanted her to pick a career path. Due to her illness it was hard to do anything together. She began the first of 3 surgeries to have her colon replaced, and my mother had a heart attack after her second surgery. I went to the hospital as much as I could, but I couldn’t make it the third time because of work (I’m an attorney with my own firm). She became angry at me for this, and, from then on, everything I did was wrong. I eventually decided that spending 3 years trying to fit a square peg into a round hole and hoping she would get her act together was enough. So, I told her I didn’t want to date anymore.

This girl immediately jumped into another relationship, and has been with 3 guys in 3 months. She tends to throw herself into relationships. (She has issues because her father abandoned the family when she was younger). She’s on her 3rd career change in 3 years, works at a mall, and is going back to school to get licensed to teach. But now she looks beautiful again, having recovered from her surgeries. I’m a little jealous that I was there to support her through all the sickness, and this new guy gets the benefit of being with a fun and healthy woman. Her new boyfriend is 30, works full-time, attends nursing school, serves in the National Guard, and is a scout master. I recently started dating a woman who is 32 and well-established, and I am amazed at how different the relationship is from the one I had with my ex. Yet, when I found out my ex now has a serious boyfriend who seems like a quality guy, I was devastated. I tend to be obsessive-compulsive about these things, and have some self-esteem issues myself, which I don’t understand given that I am dating someone of superior quality.

My former girlfriend was the closest I have ever come to someone I wanted to marry, but it seemed we were both too needy. If it weren’t for all the medical issues and her career uncertainty, I probably would have married her.

Why does it hurt so bad to see her with someone else when I was the one who ended our relationship? How can I better cope with my loss?

Our Clinical Psychologist’s Reply

The “ambivalence” your former girlfriend had about a career course, especially given the medical issues with which she was struggling (incidentally, an illness profoundly affected by stress), is fairly normal for a young woman of 25. However, the ambivalence you experienced in your relationship with her, as well as the ambivalence you still report having is not so normal for an established person of your age and may reflect dysfunctional aspects of your personality. Such ambivalence often accompanies “obsessive-compulsive” individuals. Ambivalent personalities have just as hard a time deciding when to “hold on” as they do when to “let go,” and they frequently experience much anxiety, guilt, and regret for not getting things just right.

Although personality characteristics are hard to reckon with and change, it would probably be a good idea for you to visit a counselor who specializes in personality issues and to explore whether certain traits you have might predispose you to some problems establishing and maintaining a committed relationship.