I think that  I was around 24 the last time I tried to woo a woman.  And I mean wooing her as a way to get her to like me.  And that was the last time that I went through the whole personal reflection of who I am and why women should legitimately like me.  As a young kid I was always called cute and then cute grew into handsome and that was always great to hear.  But as I started to look within myself and wonder why I didn’t close the deal with some of the bigger fish that I had dated in the past it became something that I hated to hear.  (closing the deal in this sense just means going beyond a few casual dates adn into a relatiionship.  Geez!  Nasty-minds) It seem to be so entirely surface and limited as far as an accurate description of who I was.  I never thought of myself as not having a personality but since I never really heard anyone tell me I had a great personality……how did I know?

When I was in junior high school I was like this magnet for female attention .  I smiled.  I was nice.  And I was not over wrought with the awkward acne stage that a lot of the other kids in my classes went through.  And I wasn’t one of the wayyy over developed kids who seemed to be pretty prevalent in my classes.  So I had my own little niche.  I was the cute boy who actually looked his age.  So with that, I had a lot of opportunity but still a mountain of anxiety.  I was just not really comfortable being around girls who were being complimentary of me and on top of that, being forward and open about wanting to “go with” me.  I just kind of didn’t know how to move past the early immature flirty stage to just being comfortable and being myself.  So in effect, I don’t think that I ever really got a chance to show my personality.  But being young and not really knowing who I was, I was jolted by the possibility that I just might not even have one.  And even as I got older, the progression was slow rolling as far as being more myself and letting the girls around me see it more.

High school was a huge leap in the personality department.  Mainly because my high school was a pretty intense social environment for me.  Being one of 45 black kids in a school of 1700 in suburban Los Angeles was pretty…….unique.  But the social environment with girls was pretty bizarre for me because I was a more intense person at that time because of my environment and that part of my personality came out pretty abrupt….serious…..and at times abrasive.  So while maybe that part of who I am was not the most lovable side of my personality, it was a piece of my persona that was always on blast.  I was dealing with a lot of things from the school and classmates that I was unaccustomed to and I wore my disgust on my sleeve about it.  But surprisingly it was an addition to whatever girls had liked about me before.  This was just something that got me a different type f attention from girls.  And then I realized how much I wasn’t hesitating about what to say or do.  I was just being myself.

So finally by the time I stepped on campus at Hampton University as a sophomore I had fully adjusted.  I guess you could say that my swag was on at like 89%.  I was able to navigate the sea of women with all of the spunkiness, wholesomeness, sassiness and even the slutiness that I was to encounter.  I was in cruise control.  And I knew it.  I was over any sort of nervousness that I had about the value that I had with women beyond being “cute”.  And the personality that I usually had to ease into showing people was out on free display.  Or so I thought.

Every guy gets to that point in his life where he gets hooked up with the woman who he just thinks is the BADDEST girl he has ever dated.  If you ask any guy, he can name that woman who was that girl for him at a certain point in his life.  And not that all guys reach an early peak, but it is just a feeling that overcomes you when you meet this girl.  Usually it is entirely based on looks.  And chances are, even though you stand a great chance of maybe surpassing that level of beauty over the course of your life, this moment always feels the most monumental with guys.  It happened for me around 23-24.  A girl who I had known through another association, who I always thought was stunningly beautiful, was now in my direct circle of associations and I was determined to take a crack at her.  Luckily for me she made it easy, because she was very cool and pleasant since we knew some of the same people.  Plus she flirted with enough subtlety to let me know that she thought I was attractive but not so much that she gave off the “I want you to jump my bones” vibe.  So when I got her number I was excited.  You know that butterfly feeling that you get when you meet someone.  (Sadly, that feeling has become more and more elusive as I have gotten older.) But after I got her number I felt that youthful anxiety creeping back in.  So when I called and we talked, I just didn’t feel right.  I was jumping into conversations about surface things that were stale conversation starters.  Fortunately for me she was a bit of a talker so she would carry the conversations but as we all know that is never a good thing.  I was feeling the awkward pauses on the phone.  The lack of direction in our conversations.  But even with all that, I was trying to get that first date out-of-the-way.  I was trying to do things that were maybe outside my normal courting ritual to overcompensate for not being myself when we communicated.  I was sending cards, emails, calling all the time, I even bought flowers!  hahaha…..And before I mis-represent myself, I am not saying that those are bad things.  But I believe a man just has to pick his spots for when and how he does these things.  And I was doing way too much.  Too soon.

So when that first date came around, I took her to a place that was way out of my means, wearing a pair of shoes that broke my pockets, and I bought a  floral arrangement that had me wearing band-aids on the tips of both my thumbs.  We sit down, order food and we eat…………….. I have never had a date be so excruciating.  I mean everything was awkward.  We talked over each other, talked about stuff that was uninteresting to one another and I just could not seem to say anything to peak her interest.  It was a train wreck.  The funny, witty, super cool conversationalist that I thought I had developed into was nowhere to be found.  But he was replaced by the uncertain kid that I was in middle school who didn’t know how to respond to a lady telling me that I was cute.  Think Stephon Urkelle being replaced by Steve Urkel.  Hold-up….I might have been shy but I have never been a geek!  Let’s say Drake from rap star fame to cripple Jimmy from Degrassi.  Yeah…that’s more like it.

So when I dropped her off, I knew that any chance I had with her was done.  I didn’t even know if I really wanted her like that anymore after such a lame duck performance in my part.  And that night, it just sort of clicked in my head that a lame duck performance was exactly what I had produced.  But why the hell was I performing any way?  I’m Jackson Bracey!  I don’t have to perform.  I don’t dance a jig for anyone. And in some strange way, I started to feel self-assured out of the disgust for my less than stellar showing at a date with what I thought was the baddest chick I would ever meet.  Strangely ironic that it took something like that to make me feel more confident in who I was.  And since that time I have never looked back.  I have felt more confident in dating women who have every reason to feel like a superstar in her own right.  But I always seem to keep my inner star shining through our interaction.  And I think that women appreciate that about me.  Much more than they would if I was awkwardly searching for my words and fumbling through stupid conversations.  My personality was completely unleashed and my swag on 100.  And I haven’t looked back since.  And even to this day when I see or speak to that girl I laugh to myself.  I laugh about thinking how silly that date was.  How I thought she was the baddest girl I would ever know. I laugh at how it took me being nervous and awkward to pull me through to the dude I am today.  Funny….. She’s still bad, that’s for sure….but when I laugh and joke with her now, I see two things.  How much I came into my own  after that date……and how much not getting with her turned out be the very best thing for me.