My Regrets …

(deep in thought)

…What must be remembered, I used to say… “I regret nothing, Jay only learns from it.” However, I have to say, there are decisions I’ve made throughout my life, that I regret. Those decisions have cultivated the man you see today. Some of us are able to make a mistake, a wrong-turn, encounter an aberration, or blunder, and turn it into a productive action or thought that guides our lives.  For this reason, each faux pas has added to the man you see (and hear) today.

I regret nothing,

Furthermore, my love life has been successful on many levels. As a result, I’ve learned much. Like most people, I’ve made mistakes. I write these lines to empower all men, and women to not only learn from my missteps, but to forge forward, and use your own errors as motivation. Each time I’ve miscalculated my steps in relationships and dating, I took that as power and energy to feed my desire for the love I deserve. I had to evolve into the man I am destined to be. I never take the loss as an indictment on my character. Why? In a lot of cases, the loss was meant to be. That specific journey was meant to teach me something. Essentially, it wasn’t meant to last.

That being said, I do have my regrets.


Photo Credit: Randy Jacob

When I look back (starting from high school) the old me used to say…

high school doesn’t count when it comes to my relationship count.

Admittedly, I was wrong. High school had a huge impact on the way I view women, life, and how I would navigate for the next 10 years after graduation.

I regret not acknowledging my feelings.

Surprisingly, I was a proud young man that truly believed I could do anything.  The same guy that was overconfident in his physical prowess, struggled to acknowledge his emotions. The proverbial chink in my armor.

Ask me about my regrets and I will also tell you… I wish I had handled my feelings better.

Losing love three times in high school isn’t a morale booster. All three women cheated. Each time I acted like I wasn’t phased even in the slightest. Until the last time.  I was given a breakup letter that I quietly read curled-up like a pill bug at my desk in health class. No one knew I was crying. I didn’t know what to do with what I was feeling. Me crying? C’mon… this is bullocks (the Hiberno-English version).  Feeling like so many needles pressed against my hairless chest. The relentless agony of emotional defeat was an uninvited guest at my doorstep. Failure and hurt had finally gotten to me. Consequently, I fell into depression (but that’s another story).

Ask me about my regrets and I’ll tell you.

I regret not acknowledging my feelings two years prior.


College Days

Ask me about my regrets and I will tell you. I regret that I stopped caring.

In addition, I placed an unbreakable barricade up. My heart was inaccessible. Not one woman was able to come close to removing one brick. Four years… not one. In the long run, it truly caused a reaction that would reverberate into my first “real” relationship.

College was rough for me. I was still super green with women. By my Junior year, I met someone who came into my life organically. She was a tutor in the lab where I did work-study. We became very close friends, but I never looked at her as anything more than a friend. In fact, I never looked at any woman as a girlfriend. They were all, “full-of-it.” In other words, I was carrying luggage, and plenty of it (over the weight limit with fees abundant). That being said, I was 20. How could I assess feelings like this at such an early age?

I regret not expressing my feelings

First, she was a sweetheart. No matter my mood, or situation, she was there.  My first intoxicating experience, she was there to get me into bed and nurse me back to health in the subsequent days. Second, when I struggled with Analytical Geometry, she was there to get me through. Third, she was the first woman I had sex with the college. In fact, she was the second woman I had ever been with sexually. Our chemistry was electric in more ways than one. In short, she was a bright flare of womanhood that stood before me, and I couldn’t see her. I bottled up my feelings and heaved them in the ocean never to be found for another four years. In that case, I lost her. She gave up on me. I was hopeless…

…like a penny with a hole in it

Ask me about my regrets. I’ll tell you that I regret not giving her what she deserved (my heart). Instead, I gave it to the wrong person.


Relationship Regrets

As has been noted, I have a few regrets—regardless of previous statements of grandeur.

Particularly, when I reflect back on my life, I realize that God is very clever. Each encounter and experience is developmental if you can surgically remove the piece you need, and apply it to your life strategically.

To summarize, I’ve been in five “real” relationships (all of them different). I define real as reciprocation, a mutual exchange of emotions, and a decent amount of longevity to establish and pursue goals. Otherwise, we’re just dating a long-ass time.

Ask me my relationship regrets and I’ll tell you… I regret breaking hearts.

As a matter of fact, I’ve dropped the glass a [few] times. Fractured a few hearts. I regret those actions (or lack thereof). Don’t get me wrong, I don’t live my life with regrets. I’m simply saying, if I could talk to my younger self, I’d tell him:

  • Heal, and reopen your heart for the one that deserves it. Not the one that doesn’t.
  • Make better choices in women. Not every woman deserves you.
  • Be patient, and know your worth
  • From time to time, take a break and be alone.
  • Love yourself more (you are priceless)
  • Don’t let a woman dictate what love means (and looks like) to you. Only you can determine that.
  • Hurt and pain are inevitable. Don’t let them hold you hostage and keep you from experiencing true love.
  • Give your heart willingly, not recklessly.
  • Hold her accountable. If you’re giving, and she’s only evaluating, let her go.



Photo Credit: Étienne Beauregard-Riverin

In conclusion, I am no longer afraid to get my white shoes dirty. I step in puddles and keep walking. No one can stop my two-step toward true love.

While I reflect on life as my younger self, I realize that I can’t change the occurrences of the past.  I can learn from them, and use each experience for its true purpose…

…to teach and help me evolve.

I encourage you to remember your pain and embrace your mistakes. Use them as motivation to get to the next level of love. Don’t treat loss like the end of the world. Every broken relationship is a chapter of learning and development (treat it as such).

Overall, delight in new beginnings and prepare yourself for what’s coming your way.

Each encounter, and experience is developmental, if you can surgically remove the piece you need, and apply it to your life strategically.

Do you have any regrets that you’ve lived with?