Background

I have a lull at work and thought I would give a little background on myself. Some have emailed me wondering what happened in my past to create such a callous, heartless, prick. Below is a dime-tour of the tangled wreckage of my past relationships. Surprisingly, I am more comfortable sharing this with a group of complete strangers than even my closest friends.


Cuba:
Cuba was my first college "girlfriend". We met early in my freshmen year of college and only dated for a little more than a semester. However, in college, with all that new freedom, it seemed like a fairly long time. I certainly loved her, though I never said so to her. Cuba and I broke up for many irrelevant reasons, and shortly thereafter she began dating some dude that I almost jumped on several occasions because seeing him incited instant rage. In the end I saw little good in throttling the guy, which turned out to be a good thing because he later became a good friend of mine. Cuba was a virgin when we met, but did lots of experimentation after we broke up, which ate away at me. We continued to hook up all through college, but it was only that, hooking up.


Throughout college I had tons of sex and "dated" lots of girls, but I think I compared most to Cuba, and all fell short until I met Sam the last weekend of my junior year. The two relationships were similar.


Sam:
Sam didn't go to my college, she was a "townie" and worked as a bartender at my favorite watering hole. Sam was super hot, rode a Harley, and nearly every guy at my school - and in town for that matter - pined after her. She was about 5 years older than me which added to her mystique. I am still not sure how I caught her eye, but I did one weekend just before I left school for summer break. When I got back the following fall I immediately went to Sam's bar, and she came home with me that night. Sam and I dated from August through about April that year. We got along really well, had a lot in common, but were from very different backgrounds, something we both knew would be difficult to overcome. I really liked her though, and again, was in love with her but never said anything. The relationship ended as the school year came to a close. I became very possessive towards the end, likely because I wasn't sure what to do about her. In hind sight, I was moving home that May and Sam certainly couldn't come with me, and it was really affecting me. We never formally had a fight, or broke up, I just went home and we never talked again. We both knew that the relationship had run its course.


Graduation from college was much like graduation from high school. After, I proceeded to go on an 18-month sexual bender, nailing every girl in sight. But I wasn't as naive at that point. My skin was thicker, I had been burned a few times.


My next major relationship was with Lee in my hometown. I had an apartment by then, and we spent a lot of time together. A few times, while drunk, Lee said she loved me, but I didn't feel the same (at least I don't think I did) so I never reciprocated. Eventually, Lee cheated on me with her now-husband and that was the end. I was upset at the time, but I didn't have strong feelings for her, so I got over it very quickly.


Soon thereafter Lee I was working in NYC where there are more than enough distractions to keep your mind of a cheating ex. I jumped right back into the life of wild no-strings sex like a crack addict would pick the pipe back up after a stint in rehab. It's easy to slide back into that lifestyle. I worked my way up and down the bars on the east side of Manhattan until I met the Ballerina.


Ballerina:
The Ballerina was just 17 when I met her, and I was 25. Yes, this is statutory rape in many states, but she turned 18 a few months after we met and it became a non-issue. I dated the Ballerina for a tumultuous 10-months. She said she loved me many times, but again I just didn't feel that I was in love with her, and told her so. I saw no point in lying. I did learn a lesson, here; there is a very short window to reciprocate saying "I love you" once a girl says it to you. When that window closes, if you haven't reciprocated, you have to move on. In this case that window was about 6 weeks. She became obsessed with hanging onto me, which obviously only drove me away. Clinginess is not a trait I admire.


Right after I broke up with the Ballerina I met Lando.

Lando:
I had seen Lando around town many times. I would see her in nice restaurants being wined and dined by guys who seemed much older and wealthier than I. One night I was stopped at a red light downtown and looked at the car to my left. Behind the slightly tinted windows of a brand new BMW M5 was Lando. I remember thinking, "This chick is so hot, and I see her all over town, I should find out who she is." The light changed and I didn't see her again until one night, about 8 months later. I had been laid off and was in a bar drinking heavily with some friends. Lando walked in and sat at the bar near a buddy and I. We talked for a while and apparently she took pity on me and agreed to give me a ride home that night. After that we were inseparable for a year. Unfortunately, the situation was similar to my prior two relationships. Lando was in love with me but I just didn't feel the same about her. Lando sensed this, and ultimately decided that the reason I wasn't in love with her was because I was cheating (which I wasn't). She began going through my trash for evidence, following me, double-checking "stories" about my whereabouts. Eventually I had had enough and broke it off.


By now you should see a trend. Date, break up, bang lots of girls. Date. bang. Date. Bang. After a few months and a few girls I met Jenna.


Jenna:
Jenna was a wild girl. She had lived in Europe in a jet-set crowd of finaciers and aristo-brats. When that ended she moved back to the States and hooked up with yet another millionaire, Tim, a client of mine. I met Jenna through Tim and we worked together for a while on real estate projects while she was living with him. Tim and I had a falling out (unrelated to Jenna) but months later I saw Jenna in a bar and said hello. I asked how Tim was and she said they were no longer together. I got her number and we began dating shortly after that. Jenna and I dated for about a year until I moved to DC, at which point I broke it off with her. Sometimes I think I loved her, but other times I think I was just in love with the concept of her. She was beautiful, sexually aggressive, and well traveled. People were naturally drawn to her. But Jenna had no direction in life and was unbelievably spoiled. We were not a good couple.


Fast forward two years and fifteen more random girls to Rojo. I met Rojo through a good friend of mine.


Rojo:
Rojo was the polar opposite of Jenna, which is likely what attracted me to her. She was beautiful, but she was grounded, had a good family life, and a stable career. She had a plan for her life. Soon after I met Rojo she wrote me into that plan, but her feelings for me were stronger than mine were for her. I woke up one morning and realized I wasn't in love with Rojo, and that my feelings were not getting stronger for her. I was never going to marry her, so that night I broke it off. As she left she said that she had been in love with me for many months, but was afraid to say anything because she didn't think I felt the same way. Did I mention she was smart?


Am I a brat? Am I emotionally bankrupt? Am I too immature to be in an adult relationship? Do I fear marriage? Some people would probably say yes to some or all of these, but I would like to think that there is a method to my madness. I mean, I know lots of guys who would have killed to have some of these women as a wife. But I knew that I could never be truly happy with any of them, so I would say I avoided a few divorces by NOT marrying any of them. Ultimately, I could never have been happy with any of them in the long run.


They say those that ignore history are doomed repeat it, so what have I learned? Something that is not lost on me is that, for better or worse, I seem to be seeking perfection in my mate. What is perfection, you ask? Well, I don't know. What I do know is that I seem to excel at finding flaws in my girlfriends. Certainly, what is perfect for me might not be someone else's definition, but I would like to think I will know it when it comes along.


What else have I learned? I understand that I am not a stellar communicator. I don't convey my feelings very well, and I close up when women convey theirs to me. I'm working on this.

The reason I brought all this up now is that I am really enjoying my time with Kay and want to avoid past pitfalls and let her know that I care for her. She is rebounding from a failed relationship and I still sense a lot of apprehension from her. In the end I may get burned, but I think it would be worse to know that I botched a relationship because of something I didn't say, unlike so many that I ruin by things I do say.