You know that feeling when you're standing at a literal crossroads in your life and you can almost see the "ghost" of the person you would have been if you’d just turned left instead of right? That’s basically the emotional engine behind Alison Rose Greenberg’s Maybe Once, Maybe Twice. It's a book that’s been floating around TikTok and Bookstagram for a while now, but honestly, people are still getting the core of it wrong. They treat it like a standard "who will she choose?" romance. It isn't. Not really.
It’s a story about the terrifying math of our thirties.
The plot centers on Summer Marshall, a struggling songwriter in her thirties who is staring down the barrel of two different pacts she made with two different men. One was "the one who got away," and the other was the "safety net." If she’s single at thirty-five, the deals kick in. But here’s the thing—real life doesn't actually respect the neat timelines we set for ourselves when we're twenty-two and tipsy on cheap wine.
The Complicated Reality of the 35-Year-Old Pact
We’ve all joked about it. "If we’re both single at 40, let’s just get married." In Maybe Once, Maybe Twice, Greenberg takes that trope and strips away the rom-com gloss to show how messy it actually feels when the deadline arrives. Summer is a character who feels incredibly lived-in. She isn't a 2D heroine; she’s someone who has failed, repeatedly, to reach the milestones society told her were mandatory.
The two men in question, Garrett and Cannon, represent two wildly different versions of a "happy ending." Garrett is the high school sweetheart, the nostalgia-soaked first love. Cannon is the more recent, steady, perhaps "logical" choice.
But what most readers miss is that the book is less about the men and more about Summer's relationship with her own ambition. She’s a songwriter. In the music industry, thirty-five is often treated like ancient history for a woman trying to "make it." The ticking clock of the marriage pacts mirrors the ticking clock of her career. It's stressful. It’s relatable. It’s why people are still talking about this book years after its 2023 release.
Why "The One Who Got Away" is Usually a Myth
Garrett represents a specific kind of trauma-bond nostalgia. We see this a lot in modern literature, but Greenberg handles it with a bit more grit. Most people think they want their "Garrett." They want the person who knew them before the world got heavy.
However, the book subtly argues that you can't actually go back. You’re trying to fit a version of yourself that no longer exists into a relationship that stopped growing a decade ago. It’s a ghost hunt. When Summer looks at Garrett, she’s often looking at her own lost youth, not necessarily a viable partner for her mid-thirties.
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The Music Industry Detail Most People Overlook
One of the strongest elements of Maybe Once, Maybe Twice is its depiction of the Nashville/LA songwriting grind. Greenberg actually knows this world. The technicalities of publishing deals, the heartbreak of "holds" on songs that never get recorded, and the sheer exhaustion of being a creative for hire—it’s all there.
I’ve spoken to a few people in the industry who say the portrayal of the "writer's room" vibe is spot on. It isn't just about sitting in a room with a guitar and feeling inspired. It’s about politics. It’s about who you know. It’s about writing 100 bad songs to get one "maybe." Summer’s career isn't just a backdrop; it’s the primary conflict. Her desire to be heard is arguably stronger than her desire to be married, which is a refreshing pivot from the traditional "marriage plot."
How Reproductive Health Changes the Rom-Com Stakes
We need to talk about the fertility aspect. It’s a huge part of the "why now" in the story. Summer is dealing with the reality of her biological clock, a phrase I hate, but one that carries immense weight in this narrative.
The book touches on egg freezing and the financial and emotional toll it takes. This isn't just "fluff." By including these details, Greenberg elevates the story from a simple love triangle to a contemporary commentary on female autonomy. Summer isn't just choosing between two guys; she’s choosing what the rest of her physical and familial life looks like. It’s heavy stuff.
The Problem With the "Two Timelines" Structure
The book jumps between the past and the present. Some readers find this jarring. I get it. Sometimes you just want to stay in the now. But the "past" sections are vital because they show us the why.
- They show why Summer is so hesitant to trust her own instincts.
- They explain the specific weight of the promises made to Garrett and Cannon.
- They highlight how much her musical style has evolved.
If the book stayed in the present, Garrett would just seem like an interloper. By seeing their history, we understand why he’s a threat to her current stability.
Is It Actually a Romance?
This is where the debate gets heated. If you go into Maybe Once, Maybe Twice expecting a "Happily Ever After" (HEA) that follows the strict rules of the romance genre, you might be disappointed. It leans much closer to "Women’s Fiction" or "Contemporary Drama."
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The ending is polarizing. Some people find it incredibly empowering because it prioritizes Summer’s growth over a wedding. Others feel cheated because they spent 300 pages rooting for a specific couple. Honestly? The ending is the most realistic part of the whole thing. Life rarely hands you a perfectly wrapped gift at age thirty-five. It usually hands you a choice and a lot of "what ifs."
What We Can Learn From Summer Marshall’s Journey
There is a lot of noise online about the "correct" way to handle your thirties. Get the house. Get the spouse. Freeze the eggs. Save the 401k. Summer is doing none of that perfectly.
The value of the book lies in its permission to be a "work in progress." It suggests that maybe the "twice" in the title refers to the fact that we often have to learn the same hard lessons two or three times before they finally stick. We have to fail at love "once" to understand what we actually need the "second" time around.
Actionable Insights for the "Summer Marshalls" of the World
If you’re feeling the same pressure Summer feels—whether it’s career-related or romantic—there are a few takeaways from the book’s themes that actually apply to real life.
Stop making "safety net" pacts. They sound romantic in movies, but in reality, they just keep you from fully committing to your present. They act as an escape hatch that prevents you from doing the hard work of being alone or finding someone who fits who you are now, not who you were at twenty.
Audit your nostalgia. If you’re pining for an ex, ask yourself: do I miss him, or do I miss who I was when I was with him? Usually, it’s the latter. Summer spends a lot of time untangling her love for Garrett from her love for her "uncomplicated" years.
Your "career window" is wider than you think. The book shows the brutality of the music industry, but it also shows that talent eventually finds a way if you’re willing to pivot. Summer’s songwriting evolves because her pain evolves. Use your setbacks as data for your work.
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Acknowledge the physical realities. If fertility is a concern, don’t treat it like a "someday" problem if it’s weighing on you today. Whether it’s seeing a specialist or just having an honest conversation with yourself about what you want, clarity is better than a vague sense of dread.
The Cultural Impact of the Story
Maybe Once, Maybe Twice hit a nerve because it captures the specific anxiety of the millennial generation—a group of people who were told they could have it all, only to realize that "all" is incredibly expensive and exhausting to maintain. Summer Marshall is an avatar for every woman who has ever felt like she’s "behind" on the imaginary scoreboard of life.
The book doesn't offer easy answers, and that’s why it’s good. It doesn't tell you which man to pick. It tells you that you’re the one who has to live with the choice, so you might as well pick the version of the future where you actually like yourself.
Moving Forward With a New Perspective
If you haven't read it yet, go in with an open mind. Don’t look for a Prince Charming. Look for a woman trying to find her own voice in a room full of noise.
To apply the lessons of the book to your own life, start by identifying your own "ghosts." Write down the things you’re holding onto out of a sense of obligation to your younger self. Then, give yourself permission to let them go. You don't owe your twenty-year-old self a life that no longer fits you.
Evaluate your current path. Look at your "Garrett" and your "Cannon"—not necessarily people, but paths. One represents the past, one represents the "safe" future. Is there a third path? Usually, the third path—the one you build yourself from scratch—is the only one worth taking.
Practice radical honesty about your goals. Summer had to admit she wanted the career just as much as she wanted the love. Admit what you want, even if it feels "selfish" or "unrealistic." Once it’s out in the open, the "pacts" you made with others start to lose their power over you.
Invest in your own "song." Whatever your version of songwriting is—be it a business, a hobby, or a personal goal—treat it with the respect Summer eventually learns to give her music. Don't wait for a man or a deadline to give you permission to start.
The real magic of Maybe Once, Maybe Twice isn't in the romance. It's in the moment Summer realizes that she is the only person who can write her ending. And that's a lesson that stays with you long after you close the book.