Dwight Allen O’Neal Serves “Gay Boy Next Door” Wisdom


Star of Christopher Street-The Series Releases Memoir, Shoulda! Coulda! Woulda! 

By John Stein

Dwight Allen O’Neal is perhaps best known for his starring role in the first black gay web-series Christopher Street-The Series but he has also gained a huge following from his popular podcast show, “Shoulda Coulda Woulda,” where he recounts some of his life’s biggest missteps, and reflects on how they have affected his personal journey.

Now, he’s turned his podcast show into an inspirational book of the same name.   We spoke with Dwight from his home in NYC.

Why should everyone add Shoulda! Coulda! Woulda! to their libraries?
Dwight Allen O’Neal:  I think it’s important for us all to have someone to relate to and inspire us.  My book does that for my readers.  I want them to join me on my journey through my past, and take the chance to reflect on their own personal memories.

Was it fun writing the book?
Dwight Allen O’Neal:  I enjoyed it very much. You have to be very disciplined to complete a book, and dedicate some time every day to writing it. For me it was like carving out time to hang out with an old friend and catch up on past shenanigans.  Writing this book allowed me to walk down memory lane and reflect on many good and some challenging life moments. Some moments made me laugh, others left me in tears. So much of my heart went into this, my junior memoir as I call it, because there is so much more of my story that I hope to share in the future. 

How long did it take you to complete the book?
Dwight Allen O’Neal:  Technically a little over a decade. This is literally the product of several attempts to complete the book.   Once I decided on how I wanted to release it, the book all came together fairly quickly.  It took me about two months to gather all of the content I wanted.  I then partnered with an incredible editor who made it word perfect. I guess things happen when they are supposed to.  

Which was the hardest chapter to write?
Dwight Allen O’Neal:  The hardest chapter to write was “Coulda Made Baked Spaghetti,” dedicated to my friend Tawana.  I wrote it a few days after her funeral, one of the most challenging weeks of my life. Writing it was therapeutic.  It allowed me to start healing and it gave me the opportunity to celebrate her memory.  

Was there one period in your life that was particularly challenging to live through?

Dwight Allen O’Neal:  Yes, learning that someone that I once loved was being accused of having several intimate relationships with underaged teens.  When I learned one young man’s story was eerily identical to my relationship with my ex, I was devastated, heartbroken.  And then I saw the young man was being attacked via social media and it didn’t seem fair at all.  I believed him. He was me… I was him.   When looking back on this memory, even today, there were so many more shoulda, coulda, wouldas I wish I had done. 

What are your Shoulda! Coulda! Woulda! thoughts on Black Lives Matter?
Dwight Allen O’Neal:  My heart breaks every time a new incident happens and I am encouraged that George Floyd inspired so many people into action, however, where was this attention when Trayvon Martin, Sandra Bland, or Eric Garner died?  To this day many people don’t even know who Emmitt Till is. There has been so many people reaching out to me to ask how they can help.  I do understand that they want to help now or be a part of the movement, but we shoulda, coulda, woulda did this sooner.  Also, let us not forget our queer black lives. Iyanna Dior was brutally attacked in Minnesota.  Black trans women are some of the most under protected people in our society. Many are homeless and those with homes, fear leaving them safely. Let’s do our part now so we never have to regret any more shoulda, coulda, wouldas.

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