A year ago, I decided to go back and ask all of the men in my past why they ultimately did not want to be with me. My girls were concerned.
"Isn't it just rehashing painful memories?"
"Couldn't you end up feeling awful about yourself?"
But I was tired of the "it's not you, it's me" type speeches that guys are trained to say so they don't hurt anyone's feelings. I wanted the real deal.
Now that I've gotten to the bottom of my breakups, I see that my friends were right to be worried. Men gave an assortment of reasons for my past rejections: too skinny, too controlling, not nurturing enough, not serious enough, bad cook, bad girlfriend. But I can honestly say that it was an edifying experience, one that wouldn't have been positive at all if the following conditions had not been in place.
I have self-confidence.
This experiment is the equivalent of walking into a den of fire, with nothing on but gasoline-soaked underwear. If you have not armed yourself with healthy self-esteem, you could spontaneously combust. The first guy I decided to approach was Andre, who had done the "fade out" several years back—you know, when one minute you're hanging out and talking on the phone, and then the calls get less and less frequent. We met at a diner where I told him my plan and asked him to give it to me straight. "You and I had a fun back-and-forth kind of banter, and that was great," he said, sipping his coffee. "But you weren't my physical ideal. I felt like my perfect 10 was out there, in terms of personality and looks."
Someone slightly more insecure might have been mortified by the fact that Dre's decision had come down to the superficial. And by the way, he's still looking for that perfect 10.
I know that I am a work in progress.
While I like who I am, I went into this knowing that one of these guys could tell me something that I really needed to hear. The hardest but most important piece of feedback that I got during this experiment was from Marc, who asked if he could e-mail me his response as opposed to telling me in person. He wrote, "I know you're compassionate, just not (consistently or visibly) in the soft way that I believe is most likely to help me become a better person." After some reflection, I realized that I do often save my softer, compassionate side for my work in schools, and I become a lot tougher when I get home. It was an important reminder that adults need kindness and empathy as much as my high school students do.
I no longer have any romantic interest in these guys.
This activity was intended to make me a better mate for the next person, not to repair what already went wrong with the old ones. To underscore this point, I made sure to steer clear of that one guy who still crosses my mind at unexpected moments. Though he probably has some insight to share, I'm still not ready to hear his feedback on my flaws. Part of me would be hoping that he might one day choose to overlook them.
I'm not crazy. In fact, I'm pretty cool.
A man is only going to be honest about his feelings for you if he feels that his car tires and his life will not be threatened. A good friend of mine decided that she was interested in getting back in touch with her own ex-boyfriends. The first one she called refused to see her. "He wouldn't even meet me at Starbucks," she lamented. I reminded her that the last time the two of them spoke, he couldn't even understand her through all of the hysterical crying. My girl is not in fact crazy, but her ex thinks she is, which is virtually the same thing in this situation.
On the other hand, one guy I used to date mentioned that he had regretted ending things with me because of how calmly I reacted. "You were so cool about it, like you knew that I was the one missing out. I started to think you could be right."
Before I started this journey, I had tons of questions and no answers. Instead of bemoaning the fact that I hadn't found the Barack to my Michelle, I took a deep breath, scrolled through my phone and took action. I learned what I already knew: There is nothing fundamentally "wrong" with me. I was just wrong for the people in my past. And there is absolutely nothing wrong with that, either.
Rachel Skerritt is a novelist and high school principal living in Boston.