Author Deesha Philyaw
Author Deesha Philyaw. Photo by vanessa german.

Even before she landed a seven-figure deal with a major New York publisher a few weeks ago, former Pittsburgh author Deesha Philyaw had one of the most irrepressible smiles in the business.

Philyaw’s highly anticipated 2025 debut novel, “The True Confessions of First Lady Freeman,” and “Girl, Look,” a collection of short stories, have been snapped up in a two-book deal by HarperCollins imprint Mariner Books.

Not bad for a writer who has spent much of her literary career as a freelancer, grant writer, and university adjunct who attended conferences and writing retreats, but never lacked the confidence to stack her work against better-known writers.

Philyaw’s first collection of short stories, “The Secret Lives of Church Ladies,” was published by West Virginia University Press in 2020. It was years in the making and helped establish Philyaw’s literary legitimacy at a time when no other major American publisher between New York and Los Angeles was willing to take a chance on her brand of magic realism and Black Girl real talk.

Despite limitations imposed on travel and promotion of the book by Covid, a remarkable season of vindication followed the publication of “Church Ladies.” It became a hit on Zoom and with virtual audiences and made it possible for Philyaw to cultivate a larger audience than she might have in person. 

Book cover courtesy of Deesha Philyaw.

Like Gen. Sherman burning a swath through antebellum Georgia, Philyaw, a little-known figure on the literary scene until that point, scored several major awards including the PEN/Faulkner Award for Fiction, the Los Angeles Times Book Prize and The Story Prize. That was followed by an intense bidding war for the televised rights to “Church Ladies” that HBO Max won. 

Suddenly, everyone was singing the praises of a short story collection that came out on a tiny university press situated in an obscure corner of Appalachia.

The press description for “The True Confessions of First Lady Freeman” describes it as a “biting satire of the Black church and a deeply provocative story about sexual agency, family, friendship and getting free, starring an unforgettable main character.”

“Girl, Look” is described as “a sexy, charming and poignant new collection, giving a vivid snapshot of the interior lives of Black women across generations, drawing readers to consider Black women and girls’ vulnerabilities, invisibility and beautiful contradictions, in a post-Covid, post-Breonna Taylor world.”

Philyaw answered email questions submitted about these two new projects.

Full disclosure: Because Philyaw introduced us years ago, her agent Danielle Chiotti is also my literary agent.

Tony: “The True Confessions of First Lady Freeman” sounds like a romp. You sent me several dozen pages and it is hilarious. Is this novel an extension of the Deesha Philyaw Cinematic Universe begun in “Church Ladies” even if it has no characters in common with that short story collection?

Deesha: I love that! The Deesha Philyaw Cinematic Universe. Sounds chaotic and lovely. “True Confessions” definitely comes from the same place as “Church Ladies” — my obsession with the landscape of Black women’s desires, our pursuit of freedom and our rejection of binaries, narratives and dogmas that aim to box us in.

Tony: Was it easier to slip into this story after the success of “Church Ladies” or did you feel more pressure to match its success with this follow-up? 

Author Deesha Philyaw
Photo by vanessa german.

Deesha: I’ve actually been working on this novel, in various iterations, since 2007, years before I wrote any of the stories in “Church Ladies.” I was actually on one of many hiatuses from the novel when I wrote “Church Ladies,” on Danielle’s recommendation. 

The day I turned in the manuscript for “Church Ladies” in 2019I felt a renewed confidence in my writing and in my ability to finish a book. I also felt more open to the narrative possibilities for my main character, Schar (then named “Rebecca”), and her story. So when I returned to Schar’s story, “Church Ladies” wasn’t yet out in the world. But Church Ladies‘ success did eventually eliminate my concerns around whether a publisher would want the novel. 

I don’t feel any pressure to match “Church Ladies’” success. First, that’s a ridiculously high bar, and I decided long before “Church Ladies” not to measure my success by accolades. But more importantly, it’s like having a second child. You empower her to be who she’s going to be in the world, without comparing to her older sibling. That comparison would be unfair, crippling and stifling. If I worried about “matching” “Church Ladies,” I’d never write a word.

Tony: How much more challenging is this longform storytelling for you? 

Deesha: It’s so hard! That’s one reason it’s taken me more than 15 years. The world of the novel is much larger. Pacing is a different animal. And I’m a Virgo so I’m a stickler for details, and the novel is a much larger canvas for those details. I research a lot and fall down endless Wikipedia rabbit holes.

Tony: You’re still working on “First Lady Freeman.” When do you expect to finish it in time for its 2025 publication? 

Deesha: By year’s end. Maybe early next year. We’ll see!

Tony: What’s the premise for “Girl, Look,” your second collection of short stories? Do you revisit some of the familiar, now iconic characters of your first collection or is this a new crew of indelible characters?

Deesha: Once again, I’m exploring the interior lives of Black women, our vulnerabilities and beautiful contradictions. None of the characters appeared in “Church Ladies,” however there are stories in “Girl, Look” that go into territory that I left on the cutting room floor of “Church Ladies.” For example, what if a girl whose circumstances were a lot like Olivia’s in “Peach Cobbler” –– what if her struggling, working-class mother did allow her to go to a well-off classmate’s birthday party?

In “Church Ladies,” the mother-daughter theme was prevalent but subconscious. In “Girl, Look,” I’m intentional about it. Also, there are more terrible men in “Girl, Look.” “Terrible Men” was a placeholder title in my head at one point.

Deesha Philyaw looks at herself in the mirror.
Photo by vanessa german.

Tony: I’ve often wondered to what extent your characters are based on actual people and situations. Ultimately, all fictional characters are aspects of the author, but are some characters more rooted in reality than others?

Deesha: In “Church Ladies,” I’d say “Dear Sister” was the most autobiographical story. But all of the stories have kernels of me, my mother, women I know, and real-life narratives about the Black church that aren’t unique to one person or church. In “Girl, Look,” there are more stories influenced by my experiences as a mother (vs. my experiences as a daughter, which was the case with “Church Ladies”), as well as my experiences as a middle-aged woman in the dating world.

Tony: Have you ever thought about nonfiction writing, essays, etc.? I suspect it would come naturally to you given your observational abilities.

Deesha: I write essays when the mood strikes. I have an essay on dating and trying to stay alive in the early stages of the pandemic, in an anthology titled, “Bigger Than Bravery: Black Resilience and Reclamation in a Time of Pandemic.” I have three little essays in “Nonwhite and Woman: 131 Micro Essays on Being in the World,” another anthology. Forthcoming, I have an essay in a collection on embarrassment, shame and resilience.

Photo by vanessa german.

You probably don’t remember this, but about 20 years ago, I asked you to read an essay I’d written about my father. It was about 20 pages long –– and looking back, I realize it wasn’t an essay as much as it was an indictment, like a deposition, a chronicling of every terrible thing my father had ever done. Honestly, it was a journal entry. And you were kind enough to tell me the truth when I asked you where I should submit it for publication. You told me, “Nowhere. It’s not fit for [public] consumption.” Ouch. That stung, but you were absolutely right. I didn’t write about my father again until 15 years later. By then, he’d died, I’d had a lot of therapy, and most relevant, I’d become a better writer. I’d learned to move from “journal entry” to “essay.” And I wrote this flash essay about my father, “Whiting.”

Tony: What’s the most important lesson you’ve learned as a writer on this journey, especially since getting “Church Ladies” published a few years ago? 

Deesha: I’ve learned that while writing itself is a solitary act, I need community to thrive as a writer. I need good writer friends whom I can learn from and laugh with; I need to be part of a loving squad of folks that ride this journey together with transparency and generosity, and I have that. I also need family and friends who love, encourage and support me. People –– and how you treat each other –– matter much, much more than awards. 

Tony: What’s it like being the subject of two bidding wars — cable streaming/TV and publishing?

Deesha: Weird as hell! But I’m grateful. My dream, which felt impossible, was to make a living writing. Just writing. Which is so rare. So it feels amazing to have that dream come true.

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Tony Norman’s column is underwritten by The Pittsburgh Foundation as part of its efforts to support writers and commentators who cover communities of color that historically have been misrepresented or ignored by mainstream journalism.

Award-winning writer Tony Norman tells the untold stories of Pittsburgh’s Black communities in a weekly column for NEXT. The longtime columnist and editorial writer for the Pittsburgh Post-Gazette was a Knight-Wallace Journalism Fellow at the University of Michigan and an adjunct journalism professor at Chatham University. He is the current chair of the International Free Expression Project.