Stop Trying or Try Harder

If you know me well enough to be my Facebook friend, you’ve probably been moderately entertained by the #MailmanChronicles I’ve posted over the past couple of months.

Recently however, my rendezvous with the mailman has reached an interesting point. A plateau on the side of a mountain if you will. We’ve reached a level where a decision must be made. A choice to stop trying, or try harder.

I’ve shared before that I am often a very judgmental individual, but my recent reading of the Autobiography of Malcolm X has made it ever present that I must not judge others for what they don’t know because I myself haven’t always known what I know now.

I never made it a secret that I found the mailman attractive. I enjoyed smiling at him as we exchanged meaningless “How You Doings?” and I encouraged him to stay hydrated. It was often time the highlight of my work day. You can understand then, why I was overcome with anxiety when my coworker decided to give him my number against my wishes.

The over-thinker in me panicked something awful!

*What if I don’t like the outside of work him? *Will it be awkward if we have inside jokes that aren’t related to the mail anymore?* What if things don’t work out?* What will be my highlight at work now? *What if he has a girlfriend, and this makes him uncomfortable? *Can I be hit with a sexual harassment suit?*

A bit much, I know. Here’s some background on my dating life to make this make sense for you:

  • In middle school, I dated my nemesis from elementary school. He cheated a few times, broke up with me and asked me out again before dating one of my friends our first month of high school & lying to both of us about it. I didn’t date again until the end of my Junior year of high school.


  • I wasn’t really attracted to him, but he was persistent & shared my family values. Our relationship survived my 17-day stint in China only to be foiled by his job at Shop Rite. My women’s intuition kicked in and I tried to end things as friends. We separated for about a month and a half before reuniting at his parents’ wedding. My spidey senses told me things weren’t right and I ultimately discovered that he was dating his coworker & a few other women on his community college campus. Deuces.


  • I completed four whole years at Howard University without any serious relationships and only one actual date.
  • Summer after graduation was interesting to say the least. I met this D.C. dude at Power Plant in Baltimore the weekend before starting my job in BCPS. I liked him, things worked well for a while, but we only saw each other on weekends. In the meantime, there was this handsome gentleman at my job who was often smiling in my direction. We worked in different parts of the building, but I enjoyed exchanging smiles when we crossed paths.


  • Fast forward to the end of the school year, me and the D.C. bama hadn’t spoken in almost five months and Smiles McGee and I ended up on Project Clean Up with the kids. Long story short, he made his move, we spent the summer dating only for me to find out right before returning to work that he was still living with his ex.


Needless to say it made for an awkward work environment. Instead of smiling at the mystery man I was scowling at the misery man.

I am not built to relive that part of my life at my new job with the mailman.


I realize in all these failed endeavors, be they few and far between. I was left to navigate without a blue print. Just the consultation of my unmarried mother and aunt and the knowledge of the qualities Buddha, Step Dad #1 and Step Dad #2 possessed that I wanted to avoid.

good luck traffic

So here I am, 25 years old, my longest relationship to date with an unfaithful middle schooler off and on from January of 7th grade to October of 9th grade, and I’m staring at a thread of awkward texts between me and the mailman contemplating whether it’s time for me to Stop Trying or Try Harder. Wanting nothing more than to be able to talk to one of my “Daddies” and get the insight of how a man who cares about me would suggest I identify the traits of a man who cares about me.

But then again, I’d have to believe they actually cared about me. And I’m not sure if I know the answer to that or If I want to stop trying to understand their roles in my life, or try harder.

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