Should I be queried upon the one great failing in my life (so far), I’d have to select my inability to meet and finally settle with one person.

I’ve had the fortune of dating women for long periods of time (4 years, 2 years, 2-1/2 years, 2-1/2 years) as well as short periods of time (3 months here, 2 months there). I’ve loved several of those women and been very deeply in love with at least two of them where in hindsight, I could have considered a lifelong commitment to either.

I do accept the fact that no matter how much I loved those two individuals, that perhaps they weren’t the “The One”. However, they both loved me and one supported me unconditionally as I struggled through the worst times of my life. There is a great deal of guilt associated with the failure, especially the last one, as she is unable to share my success with me.

I’ve come to realize why some of the most successful men on the planet end up with women ten or more years their junior. When you’ve finally achieved success and reached your goals and are ready to share…everything…there isn’t much choice left in your own age group.

Perhaps the most difficult issue I run into is the ability to relate to another the emotional impact that pulling yourself up from absolutely nothing brings. This unfortunately will always carry its own set of inherent issues. To quote Tupac, “I came from the gutter and I’m still here!”

I know very well that one day, as I walk down the street a multi-millionaire, I will still remember the feelings of hopelessness and helplessness. What it was like to live on a box of spaghetti for a week, or to sleep in my car, or not to be able to afford rent, or to wonder where my next dollar was coming from. The experience changes you forever.

Personally, I always imagined that I’d have someone to share my success with (as miniscule as it may be at the moment) and for now I don’t and it is a lonely, lonely feeling. Friends can bring a certain degree of joy into your life but nothing compares to having someone who knows you intimately inside and out.