Confessions of a Heartbreaker

The best relationship advice I ever received was from my mama, a woman who knew – in the biblical sense – only one man her entire life. She told me to date just one woman at a time. However, any man with options will tell you that’s easier said than done.

Even as a child I told my family, “I never want to get married. I only want to date the prettiest girls.” In my early teens I had “the talk” about women and sex with my father. He was a by-the-book type of man, so it came as no surprise when he gave me a copy of Boys and Sex during our conversation. I learned how women’s plumbing worked and how babies entered the world, but I knew little, if anything, about expressing affection.

In college I dated six or seven women at a time, often giving the same greeting card to each of them. Women who were virgins asked me if I would be their first, and life from then on was like a music video: one meaningless relationship after another.

I’ve dated my fair share of sisters-models, singers, flight attendants, attorneys, surgeons. I’ve also been with ladies who were blinded by the possibility of my being “the one,” only to later find out the hard way that they were sharing me with another fine sister with fuller lips and rounder hips. I’ve been caught cheating by E-mail and voice mail and even through underwear, when an A-cup girlfriend found a D-cup in my closet.

But one Sunday morning while spooning with an international model, I suddenly felt lonely. There I was, in bed with a gorgeous woman, but I didn’t even know who she really was. I’d never taken her for a walk or asked about her views of the world. Sure we had great sex, but I wasn’t mature enough to appreciate anything else about her. Right then I felt ashamed of my behavior. I was uncaring, unrepentant and insensitive. I thought of no one else’s feelings, needs or desires but my own. Sex was food, and I was an overeater.

Then I met Annette. She was the perfect mix of beauty and brains and sexiness. She had a warm heart and calming disposition. I loved everything about her. She forced me to take things slowly, and I didn’t mind one bit. At that point in my life, I was ready to settle down. We moved in together after about a year of dating, and I knew she’d be my wife. Unfortunately, old habits die hard, and stupidity drove me back to my cheating ways. Annette discovered E-mails from another woman and eventually told me to move out.

For the past year I’ve been trying to win Annette back. We’re talking and actually making some progress. I’ve matured a lot, and I’m trying my best to be faithful to her. But deep down inside I know that she’ll never marry me. My effort to be a good man to her now comes a little too late. I finally understand what my mother meant when she told me to date only one woman at a time. Dating several women simultaneously allowed me to compare and contrast, but it never let me cherish any of them. As a result I let a sensitive, strong woman slip through my fingers. Mama, I wish I had listened to you years ago.

Michael Keith just completed a novel based on his relationships.

Photo Credit: Peter Chin