A more approachable woman might have some of the qualities of youth and beauty that I like so much, but they generally are closer to my age- by a lot- and not the supremo uber babe/ goddess types that I can go on at length about. They generally are women I meet when I go see bands and whatnot, and they also are generally women who are friends with people I know. This makes it a lot easier for me to ask them out, put in a Facebook friend request, etc.
The last couple of women I approached who had these quaiities weren't single, it turns out, but here's another thing I like about approaching these women: they and those around them, and/ or the circumstances in which I meet them, somehow make for a more forgiving outcome even if it turns out that they are not single.
The sense that I travel on more forgiving terrain with these approachable women is what really sells the notion to me that this is where I really want to push that envelope. I mean, this terrain, let's call it that, could stand further exploration over the idea of getting up all the courage I can possibly muster to go ahead and ask out the twenty-two year old baristas and waitresses in front of God and everyone- yet again, only to come up empty- yet again.
A huge block that used to impede me from approaching less than ideal looking women has to do with my tendency to make it about my fantasy life. As an opportunity to get to know a more approachable women would present itself, I would invariably picture myself with these women at the moment when one initiates intimate relations, and the picture in my mind of that was not the pretty, pretty one that it would be with the really attractive women. So, I found it necessary to challenge my fear that any step in the direction of more approachable women would inevitably lead down the path to that moment of truth. Like I said, the last two women I approached for dates weren't even single, it turns out, so there you go. I didn't know that, in either case, nor did I even suspect it.
A couple of years ago I wrote in this space that I liked three qualities in a woman in order to get at least one date with me: available, interested, act like they give a shit about taking care of themselves. Several times I've had available women take an interest in me who couldn't manage that last one. Unresolved substance abuse issues have been a deal killer with me, even when the women in question weren't bad looking at all.
When I went to therapist and tried to talk about changing things around in my relationship with women in general, they invariably tried to steer me in the direction being in a "relationship." The problem was, this created a block when I tried to lower my standards, because I couldn't paint a pretty picture in my mind of being in a relationship with women who didn't meet my standards of youth and beauty.
I'm glad I ditched all those therapists and their advice. I just put myself in the frame of mind that I wanted to try going on dates with women I didn't normally consider, and not vie for a romantic love relationship with the first woman who agreed to go out with me a couple of times. I just got the message from the therapists I went to that I was supposed to be all hot for a relationship with the first person that came along. If that were the case, I never would have given many of the women I went out with over the course of this last ten years or so the time of day.