How do you know?


That is the question that has plagued my mind the past few months. How do you know when the time is right to settle down? When you’ve come across the right person to settle down with? You come across and meet a lot of people just being social in the city. You get to know a lot of people through dating. Many of those people have redeeming qualities that draw you to them in some way. But the question lingers…Who is the right one? And when is the right time/


I don’t want to waste my time pouring heart and emotion and effort into something that will not last. When you put in effort to something, you want the pay off of benefiting from it. I also do not want to become too selective and give up prematurely on a situation that could develop into something long lasting. It’s a difficult balance.


It’s causing me to really look at and analyze what I want. It’s not a black and white thing, not as simple as “nice” or “educated”, “fun” or “positive”…..It’s than intangible “it” factor that tells you that someone is right for you. I am wondering if it is ever that clear. If you ever really just “know” like some people seem to believe. I wonder if it isn’t about finding a “one” but rather finding one that you can make things work with…..Do I give up on the soul mate idea for someone that I can “make it work” with or do I hold out for a notion (the surefire “one”) whose validity I am starting to question.


When I look back at the past couple of years, I have been blessed to have met a lot of good women. I made a decision that, to truly give myself a shot at the one, I would open up my boundaries and my worldview, dating across all lines….race, ethnicity, social class….all different types of personalities, different levels of ambition…. Teachers, social workers, corporate types, lawyers, poets, activists, nurses, secretaries…….Phd’s to high school grads…Bougie to regular down ass chick….. I have had some great times, many great conversations, learned a lot about myself, about life. I have benefited from my dating journey. But through it all that elusive, intangible “it” hasn’t manifested itself. I am wondering if the romantic idea I have in my head isn’t some unattainable thing. If it isn’t just the product of fantasy….Screenwriters and novelists fucking with all of our heads by creating some abstract idea that doesn’t fit with reality. I wonder if it isn’t really about just finding someone cool and pushing to make it last. The self-critic in me wonders if I’m not a fucking idiot for passing certain things by, going from selective to unrealistically picky in the process. The idealist and the pragmatist within me at war. I am more of a logical person than an emotional one, which makes it tough. I cant just blindly run with feelings and get lost in them. I have to process and analyze a situation, weighing if it is really the best move.


I feel like, the longer you are single, the harder it becomes to jump back into a relationship. You get so used to your independence and autonomy, and figure that if you are going to bring someone in, they DAMN well better well be worth it. For much of my life I was a serial monogamist. From high school through college, even into law school, I basically was a relationship to relationship guy. I didn’t do a lot of “dating” really. The last several years have been different. I told myself that something had to be “lifelong quality” before I would settle into it. This perspective change was inevitable. I had been married and divorced. Once you get to that point of having that ultimate commitment, you don’t go back to settling for less. Plus, at a certain age and level of experience, you would think that the little superficial connections would cease to be fulfilling. Maturity and depth creates a need for substance, for a sense of realness. So I began to search….and search…..Enjoying the journey yet frustrated at its failure to reach the ideal destination.


I am capable of articulating what I want and what I don’t want in a relationship. There are those benchmarks that are non-negotiable…honesty, loyalty, respect, communication…..But there is so much else in addition to that. I find myself at a loss of where to find it….So here I go….walking down an uncertain path…..questioning what i’ve done, and even more unsure of what’s ahead….