Q&A: Alison Rose Greenberg, Author of ‘Maybe Once, Maybe Twice’

We chat with author Alison Rose Greenberg about her new release Maybe Once, Maybe Twice, which is filled with the romance and angst that defines the years you come to know yourself with a story of second chances and finding your own way.

Hi, Alison! Can you tell our readers a bit about yourself?

Hi! I’m Alison, and I’m an author and screenwriter living in Atlanta, Georgia with my two kids and our three unruly pets. I speak fluent rom-com, and I gravitate toward telling stories that celebrate complicated females with will-they-won’t-they romantic tension throughout. You can often find me crying to Taylor Swift.

When did you first discover your love for writing and stories?

I was a big reader growing up, but I became truly infatuated with the art of storytelling when I was a pre-teen watching late-90s WB TV series. The character development on shows like Buffy the Vampire Slayer made me want to become a writer and helped me understand the importance of story construction and authentic voices. I discovered my love for writing stories in my screenwriting course at The University of Southern California, with the late Daryl G. Nickens, who was a phenomenal professor.

Quick lightning round! Tell us the first book you ever remember reading, the one that made you want to become an author, and one that you can’t stop thinking about!

The first book I remember reading is The Baby-Sitter’s Club series. I still have nearly every copy on a shelf in my house. I have memories of staying up past my bedtime to devour the books under my covers.

This is a hard one! I am a screenwriter, and becoming an author was a (wonderful) curveball. The first book that made me interested in becoming a storyteller was To Kill a Mockingbird. The point-of-view in Harper Lee’s novel and Scout’s voice is so vibrant and different—it tugged on all my heartstrings. I would say David Sedaris’s Me Talk Pretty One Day made me wish I was an author. I have reread his essays more times than I can count.

I can’t stop thinking about Robinne Lee’s The Idea of You. It is a wildly sexy romance about a woman in her late thirties who falls for a famous boy band member, with an ending that absolutely destroyed me (in the best way). I cannot wait for the adaption with Anne Hathaway as the lead, and I’ve been emotionally preparing myself to see this book on screen.

Maybe Once, Maybe Twice comes out on October 3. What are five words you would use to describe it?

Romantic, angsty, nostalgic, heartbreaking, hopeful.

What can readers expect when they pick up Maybe Once, Maybe Twice?

Readers can expect two marriage pacts and two second-chance romances, nostalgic throwbacks to their favorite music, love stories told over the span of two decades, a refreshing best-friendship between two women in their thirties, a love letter to Trader Joe’s, summer camp romance, an honest and inspiring look at what it means to be a woman who is running out of options in both her fertility and her career, the highs and lows of being a female singer-songwriter trying to make it in New York City, a smoldering ex-boyfriend who is now the biggest movie star in the world, a decade of pining with Mr. Right Guy Wrong Time, very spicy sex scenes, a hilarious runaway pony, lust at an engagement party in the Hamptons, and more.

When you started writing this story, did you know how it would end right away, or did the ending take you by surprise?

My ending took me by surprise. The first draft ended completely differently than what you’ll read in the final version. During revisions, I had an epiphany: I realized I was fighting my gut instinct. My ending wasn’t sitting right with me, and so, I changed it. To be fair, a great deal of the book changed during revisions, but I’m grateful I gave myself the emotional space to realize the perfect ending for Maggie Vine.

What is the inspiration behind Maybe Once, Maybe Twice?

My previous novel, Bad Luck Bridesmaid, dug into a woman’s fear of marriage and her inability to accept the proposal of a man she deeply loved. It was a love story… where my main character learned to love all sides of herself. I knew I wanted to tell a different story here, about a woman stuck between a rock and a hard place in her thirties—a woman who wants a family, but who isn’t where she wants to be in her career. Those two dreams are at war for a lot of women as they reach a certain age—and a handful of my friends are going through this battle right now. The plot came to me in a meeting, where someone mentioned the broad idea of a marriage pact that a man in his twenties made with two different women. I wasn’t intrigued by the idea of a man getting all the choices: society and biology aren’t holding a man in his twenties at gunpoint and telling him to have his life figured out, or else. What intrigued me was a woman in her thirties dealing with her past and present, as two of her great loves show up at a time when it looks like all the doors are closing in her face.

What are you working on now?

With the WGA strike halting screenwriting, I am working on my third novel now, and I cannot wait to share more soon.

Will you be picking up Maybe Once, Maybe Twice? Tell us in the comments below!

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