D. Watkins is an East Baltimore-born author, editor, professor and, most recently, writer for HBO’s “We Own This City.” But those titles don’t quite get to the root of who Watkins, the everyday person, is. His favorite pair of shoes are the Black Cement Jordan 3s, just like a normal sneakerhead. A good chunk of his Instagram feed is his toddler daughter. He cusses as frequently as bad-mouthed middle schoolers. And most notably, Watkins doesn’t shy away from acknowledging his faulty mindset during his hustling years, nor does he portray himself as a perfect born-again Christian now.

Watkins’ success doesn’t follow the typical career arc of most writers. Prior to his latest book, “Black Boy Smile: A Memoir in Moments,” he authored “The Beast Side: Living (and Dying) While Black in America”; “The Cook Up: A Crack Rock Memoir”; “We Speak for Ourselves: How Woke Culture Inhibits Progress”; and teamed up with Carmelo Anthony for the Baltimore-raised basketball star’s autobiography, “Where Tomorrows Aren’t Promised.” In “Black Boy Smile,” Watkins revisits moments that shaped his mindset, personal relationships and definition of “manhood.” Unhealthy coping mechanisms used at a young age are a reoccurring point of emphasis throughout this retelling of his life. At his office at the University of Baltimore, where he is a professor, he spoke about the new memoir and what it took to make it.

Cover of Black Boy Smile by D. Watkins (Courtesy photo)

“Black Boy Smile” is an oxymoron in a sense because you rarely smile throughout the book. Can you explain the thought process behind the title?

I initially wanted to call the book “Smile,” because there are some dark moments. But I found joy in the midst of a lot of those dark moments. So, if you pick apart every piece of pain, there are elements of joy inside of that pain that gave me an opportunity to smile. Now the difficult part was the fact that happiness is perspective-based, you know what I’m saying? The demographic that I thought about when I was writing the book were these kids that I see in the schools and the jails that I visit all the time, whose lives are just riddled with shit that they shouldn’t have to go through. So, I wanted them to understand that I made mistakes, I did bad things, I’ve been through stuff, the people who raised me did bad things, they’ve been through stuff, but we were able to smile and grow — so y’all can do the same thing.

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Affection wasn’t something that was emphasized to you in your household while you were growing up — can you discuss the toll that may have taken on you and other Black males?

It’s very important, because the result of just living a life of not hugging and not being told, “I love you,” as a grown man, right now, I still feel awkward doing those things. It just wasn’t a part of my makeup. Even before COVID, I’d do the quick church hug and get off extremely quick. That being said, I hug my child and my wife every chance I get, because I know what that has done to me and I would not want that to be given to them. I say that to say, us Black males need those real, meaningful relationships and to be given that affection and given that love. Because, coming up we were rewarded for being tough and cold. But that’s clearly not a good thing.

This lack of affection deterred relationships with several characters in your book. Your wife — before the two of you started dating — asked you about a potential relationship that you turned down because you didn’t believe somebody could love you and you weren’t secure with your financial status. Your friend Dirty Larry attempted to console you as you coped with the death of your cousin, and you responded by ridiculing him.

When it came to Larry, I was out of line. I was out of pocket and I was wrong. I was embarrassed that I couldn’t hide my emotions as well as I normally do, so I tried to shift focus. You know, it’s difficult to say that. Even now, years later, it’s difficult to admit that I was wrong. And I never made amends with him. It’s crazy because two years ago, I’d seen him on Greenmount asking for money. I pulled over and gave him a couple of dollars, but I didn’t say anything. I gave him like $150 as opposed to the normal $10 as my attempt at an apology, but I didn’t formally apologize. That was my mentality and it’s clearly flawed. Maybe it resonated with him, maybe it didn’t, but it wasn’t right how I treated him years ago and it wasn’t right how I “apologized.”

I think when it came to my wife, that ties into the masculinity thing. Who’s going to fully respect the person who doesn’t have any money? And it directly connects to that. She didn’t want me for my money. She had her own money, and she didn’t need me to come take care of her. She wanted to build with me and I was too foolish to see it. Because I couldn’t think past what somebody would say about her broke boyfriend. When I was coming up, 13-year-old girls were comparing us to rappers like Jay-Z. We couldn’t even grow up first. And instead of me growing out of that thought process of comparing my life to other, more established people, my ego wouldn’t let me fathom the thought of just being loved for myself.

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Something that you constantly reiterate in “Black Boy Smile” is that you’re a private person, so you choose to omit certain things. How difficult is it being an author opening up about traumatizing events?

I’m probably not even that private, I think I’m just scared to touch on certain things, right? It’s hard for me to sell a book and reflect on the amount of murder that I have been around in my life. As far as people close to me dying, it’s hard for me to tell those stories. It’s hard for me to go there because sometimes I feel like I don’t know if I can come back when I go deep on the impact that some of those things that have had on my life. I don’t even look at old pictures on my social media anymore because most of the people in the first half of my Instagram are dead. So to talk about it in passing is one thing, but to sit down in front of that blank page and pour out what that is and what that means is difficult for me, and it’s also very heavy for the reader. This book has heavy parts, but you have to be careful because people read to learn. People read to be entertained, but people don’t always read to feel sad. So you have to think about those things and balance that.

One of the goals for this book was to not glorify what we go through, but to process it and be uncomfortable. By being uncomfortable, we get closer to becoming our authentic selves and who we are as people.

That’s similar to Kendrick Lamar’s latest album, “Mr. Morale & the Big Steppers,” in the sense of us tackling events that shaped us head-on, no matter how uncomfortable they make us.

I actually went on Tamron Hall’s talk-show the other day and she mentioned the track “Father Time” off that album as a direct comparison. The parallels to that album are crazy. For people to make that comparison, it makes me think that we may be entering a new level of consciousness, when men are starting to question their father issues and question their relationships. Maybe we’re getting into this place where we’re understanding that we’re doing it wrong. I was thankful for her and for you making that comparison. I was also thankful for the album, because this next level of consciousness can be better for society as a whole. It’s a paradigm shift in our priorities and our value systems. My thoughts now aren’t only just reputation and my money, now it’s values like my wife, my daughter, my integrity, how I treat people, and things of that nature.

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