Author Interview: Try Your Worst by Chatham Greenfield

Chatham Greenfield’s Try Your Worst is a romcom that mixes prank wars, tourist-town shenanigans, and a rivals-to-lovers romance that’s as heartfelt as it is hilarious. Sadie and Cleo’s journey from lifelong enemies to something much softer is full of laugh-out-loud moments, swoony surprises, and a tender exploration of what it means to be loved without ever being “too much.” In our conversation, Chatham shares how they balanced chaos with vulnerability, why small moments of connection mattered most, and the joy of turning a rivalry into a love story readers won’t forget. Check out our interview below and pick up Try Your Worst, out now!

Try Your Worst

by Chatham Greenfield
Published by: Bloomsbury
on September 23rd, 2025
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I Kissed Shara Wheeler meets The Agathas in this cozy mystery about two rivals forced to team up to figure out who is framing them for crimes they didn't commit.
Sadie Katz and Cleo Chapman have been rivals since birth. Literally. They entered the world competing to be the first baby born in the new year, a title Cleo ultimately won. And she’s been nonchalantly winning at just about everything since—much to Sadie’s chagrin. Now in the fall of their senior year, Sadie and Cleo are neck-and-neck for valedictorian. But when a string of increasingly serious pranks take over their school, the perpetrator deliberately sets up Sadie and Cleo to take the fall.
Suddenly expulsion is on the line, and the only way to clear their names is to join forces and search for the culprit. As their investigation progresses, the girls begin to question more than suspects. Sadie, struggling with depression and academic burn out, finds that her ivy league dream doesn’t seem as appealing as it once did. Meanwhile, Cleo wonders if it's time she start fighting for what she wants, rather than passively accepting whatever comes easiest.
With their futures on the line, the two grow closer, and both start to ask themselves: Are they really meant to be rivals? Or were they always destined to become something more?

Interview with Chatham Greenfield

Rival-from-birth is such a fun premise. Once you threw Sadie and Cleo together, what surprised you most about how they clicked (or didn’t)?

Rivals-from-birth was so fun to write, but tricky too. I love the tension, but I never want readers to think, “Wait, I thought she hated her? Why’s she making heart eyes now?” I want them to really resonate with the slow stumble from hatred to adoration. 

What surprised me most was seeing all of the cracks that formed in Sadie’s walls as she fell for Cleo. She buys into the rivalry much more than Cleo does, so I was worried I wouldn’t be able to pull off that shift. In the end, I found it worked most by zeroing in on tiny moments of tenderness, some of which happened even when I least expected them. It was a delicate hodge podge of stolen glances, shared jokes, and Sadie’s realization that something about them works despite them being so different.

Between the prank chaos and the romance build-up, there’s a lot going on. How did you keep both the shenanigans and the feelings turned up to eleven?

One of my favorite notes I got from my editor when working on this book was “make it sillier.” The exploration of Sadie’s depression can be heavy, especially for readers who have been there themselves, and I wanted to balance that out with lightness. The setting helped. Tourist towns are weird and I’ve always wanted to explore what it’s like living in one, rather than just passing through.

It also helped to really dial into what Sadie and Cleo would be feeling during the investigation. Everything’s so heightened for them, and they’re forced to spend time with this person who’s so different than they expected. I tugged at that thread of surprise as much as possible, of “I’m used to only seeing this person in math class but seeing her here, on a horse drawn carriage in the moonlight wearing a ridiculous costume, she’s actually kind of charming and different from the version of her I’ve built up in my head.”

You’ve said you want readers to know they’re never “too much.” What’s a moment in Try Your Worst you hope makes someone feel that in their bones?

The moment that immediately comes to mind is when Sadie has a breakdown and cries to Cleo. It’s from Cleo’s point of view, even though Sadie’s the emotional center of the chapter, and that was important for me. I wanted readers to see that Sadie’s pain and vulnerability didn’t alter Cleo’s feelings for her—that she could never be “too much” for Cleo. Cleo will always want her and always want more of her, not less. Moments like this show up not just with Cleo, but with Sadie’s parents, too. I wanted to show readers the type of love they deserve, one that never requires them to shrink themselves down or minimize their own feelings.