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20 First Dates - Part One

I've always been a relationship person. Whether that relationship was a few short months before I moved on, or longer, I have never been a good dater. I like the adventure of meeting someone and figuring out, one person at a time, if they're a good fit. I wrote a poem at age 13 or 14 that apparently was controversial but still won the school wide poetry contest my freshman year of high school; it was about finding myself, but it applies really well here.


I was born white in a black person's body in a tan person's soul

and though I struggled to get out

no one understood

that I was slowly changing shades

trying on different ones to give me different views.

I felt eventually I'd find myself and the color that

was right for me, but meanwhile

I'm stuck

with twelve pairs of sunglasses.

After leaving a 17 1/2 year relationship and marriage, it definitely felt like I was starting all over with my identity - trying on different shades to figure out who I was and, more deeply, what I wanted in a relationship. I had some stumbles and dated a couple of people before my bestie and biz partner sat me down and challenged me to go on 20 First Dates. Let's be real - the number was arbitrary. It was really a challenge to change my mentality. The first time around, I was in my early 20's and my entire though process was, what kind of person do I want to be with to feel secure. Which is a very separate question from, what do I need and want out of a relationship, to feel fulfilled.

Let's be very clear. I know I am a lot to deal with - I am a single mom with a full time job, two dogs, side gigs, multiple charity commitments. I need someone super secure in who they are, who is willing to dress up or dress down, and feel comfortable in all environments. I worked my tush off to get here, and am not willing to settle. So you, my dear reader, get to experience the journey of me learning to date and learning what I need in a relationship. I also want to hear YOUR stories and journeys! And if you're one of the 20 First Dates, don't worry - this isn't about you ;). May my journey of discovery help some of you as well.

Written by Anika Jackson. Mother, community volunteer, philanthropist, and socially conscious fashionista ambassador. Team Member of Real Beauty Real Women and CEO of Philanthropic Fetes. Check out our latest project, Social Graces Social Club! Contact her at

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