Dwight Allen O’Neal Tells All in New Memoir

Dwight Allen O’Neal, star of the first Black, gay web series Christopher Street: The Series, is out with his first book, Shoulda! Coulda! Woulda! Based on his popular podcast of the same name, Shoulda! Coulda! Woulda! is a collection of humorous vignettes where O’Neal recounts some of his life’s biggest missteps and reflects on how they have affected his personal journey.

O’Neal has been tagged as the gay boy next door because he helps his audience by sharing with them things he wished he knew before making various life choices in his personal life and career. From learning to break out of his self-imposed shell to coming forward in a very public sex scandal, Shoulda! Coulda! Woulda! will make readers laugh, cry, and go WTF?!

OUT FRONT had the opportunity to talk more with O’Neal about Shoulda! Coulda! Woulda!, why being a lifestyle expert is important, and the start of his new nonprofit foundation, Beauty with a Cause (BWAC).Hi, Dwight! Thank you so much for taking the time to chat with me about your new book Shoulda! Coulda! Woulda! Without giving too much away, can you tell us more about it?
Basically, Shoulda! Coulda! Woula! is a companion piece to my podcast which shares the name. My podcast is a platform where I talk about difference experiences, how they have affected me, and how they have helped me grow and develop me into the person I am today. I felt like some of the stories that I shared needed a little bit more depth, and I was able to do that in a book. I wanted to create something that would allow me the opportunity to share those various stories, inspire people, motivate people, and entertain them in general.

What specifically inspired you to write this memoir?
Honestly, I have been trying to write a book for the past 12 years [laughs]. It’s not the first time. The first time, I was part of a public scandal, but I didn’t get involved with it with my name. I went as John Doe because of work and I was a bit embarrassed for my family. I got into a relationship with someone while I was underage, and some people came forward. It was a celebrity figure, and I just chose to keep my identity hidden.

One of the things that helped me cope through that situation was writing. I started working on something, and I finished it, and I was like, OK, I can’t put this out. Then I started writing on another idea and then another idea. So, when I started the podcast, I ended up actually, you’re the first to hear this, I got a reading from an oracle. He was like, you should have written, like, four books already. I started laughing. I’m like, I have actually written three. He said he felt a fourth one, and that inspired me to kind of take things I have already written and I literally broke it apart.

I was able to find ways of tying the chapters together in a unique way. With the success of the podcast and that format really working, I found a formula that I was passionate about, and here we are today with Shoulda! Coulda! Woulda!

Why is being a lifestyle expert so important to you, and how did this journey begin?
Honestly, I think being a lifestyle expert as a gay man, especially a gay man of color, is important because so many young people have no one to look up to. I actually dedicated my book to Carl Joseph Walker-Hoover. He was a young boy who killed himself when he was 11 years old. His mom was on Oprah many, many years ago talking about how kids picked on him at school. He played baseball, but he was effeminate, and kids bullied him. Carl ended up hanging himself at home. So, I saw this story on Oprah, and I remember sitting on my mom’s couch bawling for hours. I don’t even know this kid, but hearing his story, he sounded like me. This was around the time of the whole “It Gets Better” movement started.

This story touched me, and I adopted him as my little brother in my head. So, whenever I am using my platform, I have this young boy in my head. That there is a young kid out there that needs to see a Dwight. They need to hear the stories that I have gone through. They need to know that it gets better. It really does, and I think it is so important to have role models and lifestyle media personalities that people can relate and look up to.

Thankfully, they are seeing more us. From Andy Cohen to Anderson Cooper, Billy Porter, Laverne Cox, it is important to see these various figures, and we need more of them to come forward so these people can find someone they can relate to, inspire to, look up to and be like. That story just really stuck with me, and again, I dedicated my book to him. When I finished my book, I actually tried to find his mother to send her a copy, and I found that she passed away. Died of breast cancer at 51, and I cried all over again because I wanted her to have the book because I dedicated it to her son. We need to have more people that will stand in their greatness to inspire others because it is harder for a queer child to have people to look up to and want to be like.

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How has Shoulda! Coulda! Woulda! been received so far?
It has been receiving great feedback and reviews, and that part’s so tricky when you release something, especially something so personal. You don’t know how the world is going to respond to it. The timing of my book was just insane because it came out a couple weeks ago when there was a lot going on with Black Lives Matters, but then also Black, queer lives mattering, and I was just like, Dwight, the timing of this book is really bad. I didn’t even get a chance to promote the way that I wanted to. I took a pause to really get behind the cause and to use my voice and my platform in a positive way, but people have still been talking about it and sharing.

Individuals are reaching out to me, so it has been received very well, and the feedback has been awesome. One reviewer said it’s a great introduction to people that don’t know who I am, and it is also great to fill in the gaps to those who do know who I am and learn something new about me because I am very raw, very open, and very real with each chapter. Whether the chapter makes you laugh, cry or think boy, what the hell is wrong with you, you still learn something about me. It definitely allows you to look at yourself and really inspire yourself to do greatness and live your truth.

I am glad you mentioned Black Lives Matter because that was my next question. I saw that you talked about the movement on a recent episode of the podcast. Can you tell us more about your thoughts on the current situation and the national protests?
Yes, I did a short episode because I honored blackout Tuesday, and I typically film my podcast on Tuesdays or early Wednesday morning. For me specifically, it has been challenging because I feel like this has been going on for so long, and I feel like it’s just getting public attention now. I think it is really sad that people have to ask for Black lives to matter, that we have to ask for LGBTQ equality, that we have to ask these questions. My ancestors had to ask for civil rights. Think about it. If your partner tells you I love you, and the response is well, I love everyone, how does that make you feel? So, when you hear the response, well, all lives matter, yes, we know all lives do matter. However, if that was the case, there would not be a Black Lives Matter movement today.

The other thing that upsets me is that, within the Black community as a gay man, as a part of the queer community, I don’t feel that my life matters. I feel my life matters only if I’m straight. Only if I identify as being a straight, cisgender male or female, and that’s not fair. I think we all need to take a pause. We need to look and analyze how we treat people, and we need to go back to the golden rule. Do unto others as you would have them do unto you. That is what it rally boils down to. I hate what has happened in the world. However, I am excited that because of what’s happening, we will have a brighter future. I do think this is the first step of legitimate change within the world.

I agree. I believe the message is getting across, and it is not falling on deaf ears.
It’s not. I am so happy that I have had so many people reach out asking how they can be involved. How can they help, and the answer I give is, it’s like a puzzle. Think of a puzzle. A puzzle has various pieces. Some pieces are big, some pieces are small, and we need all of those pieces in order to complete the picture. So, whether you are bringing a smaller piece to the picture or a bigger piece, it is all needed to make changes. It’s all needed to make this picture complete, and we can’t do it without the individual puzzle pieces, which means we can’t do without one another.

Exactly. Now, shifting back to Shoulda! Coulda! Woulda!, what was the writing process like for you, and how scary was it to know that you are sharing your life with the world?
[Laughs] So, the writing process, it takes discipline, but I enjoyed it. Each day, I challenged myself to write a minimum of two chapters, and it was like going to catch up with an old friend. As I walked down memory lane, some of the memories were easier to talk and write about, while some of the other memories were a bit more challenging. I think the hardest part was reading something or finishing a chapter, and think, my mom’s going to read this.

There’s this one chapter where I make a joke where I’m not saying bad words. I’m putting like an F, then a star, star, star. Like, I’m not going to curse within this sentence because I just used my mom’s name in the same sentence. So, that’s where it was tricky, but my mom has already read the book, and she is very proud. She said she felt like she got to know who I was, and that made me happy, but it also made me sad because that means that my mother never really fully knew me.

I talk about my mentor in the book as well who passed away in 2015, and my mother knew of him through me, but she never met my gay mentor because my mom was in Arkansas, and I’m in New York. She was like, I finally felt like I got to really know Nathan, and I’m so happy you met him because clearly I didn’t prepare you for the world, and he did. I’m like, no! You did, of course, but there were things that he taught me that she never would have been able to know. So, I’m happy that I wrote a book just so that my mom can even feel like she really got to know me and still loves me regardless.

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Can we expect more books from you in the future?
Yes, you can be on lookout for more books. I definitely enjoyed the process, and I am excited that the story is so inspiring to so many people.

Outside of being a lifestyle expert and now author, you are also an actor and producer. Do you currently have any projects in the works?
I actually do. I am currently working on a movie project, and then my business partner and I have been working on a short film that was filmed throughout the pandemic. I am also in the process of starting my own nonprofit organization. I recently just got my fiscal sponsor, and the name of the organization is BWAC, which is Beauty with a Cause.

Basically, the organization is going to have a hyper focus on the trans community and help them get work in the beauty industry. So, especially with people losing their jobs with the pandemic, my focus is actually to work with beauty brands as they figure out what the new normal is going to look like for employment, and my organization is going to help get people within the queer community jobs in beauty. This is something I am very excited and passionate about.

That’s amazing, and I wish you the best of luck with BWAC. Is there anything else you would like to add before we wrap up?
Nothing I can think of off the top of my head, but thank you so much for taking some time out of your day to speak with me. It was an honor, and I cannot wait to see the finished piece!

Thank you, Dwight. It has been an absolute pleasure!

Shoulda! Coulda! Woulda! Is now available on Amazon. For more information and to stay up-to-date, visit ONealAppeal.com, or follow O’Neal on social media.