Shoulda! Coulda! Woulda!: gaylebrity Dwight Allen O'Neal spills the tea
16 Jul 2020

by Drew Rowsome - photos by Rick Day

Dwight Allen O'Neal is an actor, producer, fashion model, celebrity fashion stylist, lifestyle guru, motivational speaker, influencer, and currently hosts a podcast. He is also a "gaylebrity" and bills himself as "the gay boy next door." Shoulda! Coulda! Woulda! is his "first" book. A book that is as scattershot but compulsively readable as his resumé.

Throughout Shoulda! Coulda! Woulda!, O'Neal states several times that celebrity was always his goal, whether it be as an actor, a talk show host, or just famous. He also says that he always wanted to be an author. An author of several books. He does cram a lot into Shoulda! Coulda! Woulda! but never quite decides why he is writing it or how it should hold together. And for someone who claims to have no secrets because he's "lived my life on YouTube," he can be sadly reticent about many things.

That is not to imply that Shoulda! Coulda! Woulda! is not a lot of fun, an easy read (except for the desperate need for a copy editor), or that it doesn't contain some sage advice. Shoulda! Coulda! Woulda! begins as a snapshot of the frenetic world of the hustle to become any of the career designations O'Neal wears. He offers not nitty gritty details but rather an attitude adjustment that is taken to heart all the more so for not being a lecture, but rather couched in humour and anecdotes. Entrepreneurism with heart.

Then Shoulda! Coulda! Woulda! veers into stories about his love life intersecting with his career. It is hard to believe that even the naif he tends to paint himself as, would be surprised to be "ambushed" on something he refers to as an "online reality show." O'Neal's love life will, after that confusing chapter, continue to be an influence on his writing. A smart, sweet and ultimately heartbreaking chapter on cooking and friendship, is followed by a flat-out stand-up routine on RBF (Resting Bitch Face). The flashbacks woven through to form the memoir portion of Shoulda! Coulda! Woulda! are all sharp, funny and well-observed.

His mother offers great advice about shade, and the tale of his best friend Duncan, a can of hairspray, and penis size is delightful. Shoulda! Coulda! Woulda! is like catching up with an old friend who begins a monologue with bravado, digresses, shares favourite tales that may mean more to them than the listener, becomes more revealing as the telling continues, and eventually wends around to the real point of the sharing. The last two chapters of Shoulda! Coulda! Woulda! - "Coulda Spilled The Tea" and "Woulda Preferred Light Skin" - concern a traumatic sex scandal and O'Neal's role in it.

The scandal will be familiar to many, and O'Neal's breathless comedic voice expresses perfectly his confusion, guilt and lost innocence. The lifestyle advice on how predators work and the process of grooming is concise and taut. And it totally reframes the entire book, echoing back through the pages and stories to create a quite different portrait of who O'Neal is and of who he could be. And who he coulda been. A life lesson to be taken to heart. 

Unfortunately at that point Shoulda! Coulda! Woulda! effectively ends. Abruptly. (Except for a bittersweet muddled "Epilogue" that returns to romantic misadventures and "Acknowledgements" that are almost as long as any of the preceding chapters.) O'Neal is either unwilling or uninterested, or possibly afraid of, continuing the self-analysis, of digging deep, that would have made Shoulda! Coulda! Woulda! a powerful statement. He teases that there is another book coming (he intends to write nine because that is his lucky number) and perhaps that one will grapple with the themes he skims over here. Shoulda, coulda woulda indeed. There is a real need for writing on what it means to be black and gay and ambitious in this world, in the entertainment and celebrity world. What it means to have survived child abuse. And advice on becoming a successful gaylebrity. Until then, Should! Coulda! Woulda! is a fun, enjoyable teaser.