How to Write a Gender-Flipped Retelling That Actually Works
Gender-flipped retellings are everywhere these days.
Pick up any YA fantasy section and you'll find female King Arthurs, girl pirates, and warrior princesses reimagining classic tales.
But here's the thing—a lot of them feel forced, gimmicky, or like the author just did a find-and-replace on pronouns and called it a day.
Then there's Kara Connolly's No Good Deed, which proves that gender-flipped retellings can actually work when they're done thoughtfully.
Connolly doesn't just give us "Robin Hood but a girl." She gives us Ellie Hudson—a snarky, Olympic-level archer who accidentally time travels to medieval England and becomes the legend we know. The difference is night and day.
So what makes Connolly's approach succeed where so many others fail? Let's break it down.
Give Your Protagonist Skills That Actually Matter
The biggest problem with most gender-flipped retellings is that authors swap the gender without considering the logistics.
They'll make their heroine a master swordsman without explaining how she learned to fight, or have her outshoot trained soldiers because...girl power?
Connolly sidesteps this entirely by making Ellie an Olympic-level archer. Her skills are established from page one—we meet her at archery trials, we see her training regimen, we understand that she's been doing this her entire life.
When Ellie picks up a medieval bow and starts hitting impossible shots, we don't roll our eyes. We believe it.
This isn't just about combat skills, either. Your protagonist needs to bring something concrete to the table that makes their version of the story feel necessary.
Ask yourself: what specific competence does my character have that would change how this classic tale unfolds?
Don't Make Gender the Only Point of Difference
"What if [insert male character] was a woman?" isn't a complete premise.
It's barely even a starting point.
Too many authors think swapping gender is enough to justify a retelling, but readers can sense when that's all you've got.
Ellie isn't just female Robin Hood:
She's a modern teenager with 21st-century sensibilities about justice and fairness.
She's dealing with family trauma (her brother's death) that drives her moral compass.
She's sarcastic, impulsive, and has zero patience for medieval gender expectations.
All of these traits would matter regardless of whether she was male or female.
The gender flip should unlock new story possibilities, not just create a marketing hook.
What does your protagonist bring to this tale that goes beyond their gender?
What unique perspective, background, or motivation changes the story in meaningful ways?
Address the Practical Challenges Head-On
One of the most frustrating things about many gender-flipped retellings is how they ignore the practical realities of how gender would actually affect the story.
They'll drop a modern woman into a historical setting and pretend that won't create any complications.
Connolly doesn't make this mistake.
Ellie disguises herself as a boy because she understands that medieval England isn't going to accept a female outlaw leader. She deals with the awkwardness of maintaining this disguise, the constant threat of discovery, and the frustration of having to hide her identity to be taken seriously.
This isn't about being historically accurate for accuracy's sake—it's about acknowledging that gender matters in your story world.
If it doesn't create any complications or challenges for your protagonist, then why did you flip it in the first place?
Subvert Expectations, Don't Just Reverse Them
Taking a male character and making them female without adding any new layers doesn't create depth—it just creates a mirror image.
Connolly's twist is that Ellie doesn't just become Robin Hood—she becomes Robin Hood through time travel, bringing modern sensibilities to a medieval legend. This creates genuine story tension.
How does someone with 21st-century ideas about justice navigate a world where might makes right? How does a teenager used to modern conveniences survive in medieval England?
The time travel element isn't just a gimmick—it's what makes the gender flip meaningful.
Ellie's modern perspective on women's rights, social justice, and individual agency creates conflict and character growth that wouldn't exist in a straight historical retelling.
Don't Weaken Other Characters to Make Your Heroine Look Strong
One of the most common mistakes in gender-flipped retellings is making all the male characters incompetent, bumbling, or useless so the heroine appears more capable by comparison.
This isn't empowerment—it's undermining your protagonist's actual strength.
Connolly gets this right in No Good Deed. Sir James is skilled, intelligent, and capable. Will Scarlett and Little John bring their own expertise to the group.
These supporting male characters don't need to be diminished for Ellie to shine.
In fact, the fact that these competent men respect her leadership makes her more impressive, not less.
Your heroine should be remarkable because of who she is and what she can do, not because everyone around her is incompetent.
When you surround her with other capable people who still recognize her unique value, you're showing real strength.
When you make everyone else weak to prop her up, you're undermining her by suggesting she cannot be strong unless other characters are made smaller.
Avoid the Romance Trap
This is where so many YA gender-flipped retellings go wrong.
They start with a promising premise—strong female protagonist taking on a classic male role—and then immediately bog down in romance. The heroine spends more time swooning over her love interest than actually being heroic.
Connolly includes romantic elements, but they're secondary to adventure and character development.
Ellie's relationships with Sir James and others support her growth as a leader, but they don't overshadow her heroic journey.
The romance serves the character arc, not the other way around.
Ask yourself: if I removed all the romantic elements from my story, would it still be compelling?
If the answer is no, you might be using romance as a crutch instead of developing your protagonist's heroic arc.
The Secret Sauce: Character First, Concept Second
Here's what it all comes down to: the best gender-flipped retellings work because they're about character, not concept.
Connolly didn't start with "What if Robin Hood was a girl?" She started with Ellie Hudson—a specific person with specific skills, flaws, and motivations—and then asked how that character would handle finding herself in Robin Hood's shoes.
Your gender flip should feel inevitable once readers know your protagonist.
Of course this particular character would end up in this particular situation.
Of course they would handle it this way.
Of course this would be their version of the classic tale.
When you get that right, the gender flip stops feeling like a gimmick and starts feeling like storytelling.
And that's when readers stop rolling their eyes and start turning pages.
The best retellings don't just ask "What if the gender was different?" They ask "What new story does this change unlock?"
Answer that question well, and you'll have a retelling that actually works.
