10 Ways to Write a Dramedy Like Issa Rae’s Insecure

Loved HBO’s Insecure? Here’s how to write like Issa…

Writing a dramedy — a blend of drama and comedy — is no easy feat.

But Issa Rae’s Insecure has mastered the art of juggling real-life drama with hilarious, awkward moments.

If you’ve ever found yourself laughing one second and feeling heartbroken the next while watching the show, that’s the genius of dramedy at work.

Rae’s writing offers a goldmine of lessons for anyone looking to craft their own blend of humor and heart.

So how do you write a dramedy that hooks people in, much like Insecure does?

Here are 10 ways you can channel your inner Issa Rae to create something just as real, funny, and poignant.

1. Keep It Real

Issa Rae doesn’t sugarcoat anything.

Insecure is beloved because it paints an authentic picture of relationships, careers, and even those cringe-worthy moments in life where you just want to curl into a ball.

Whether it’s showing Issa rapping to herself in the mirror or struggling with her job, the show feels genuine.

For your own dramedy, aim for that same rawness.

Write characters that are flawed, human, and sometimes downright messy.

They should be relatable, like the friend who says exactly what everyone else is thinking but is too scared to admit it.

No one wants a perfect protagonist.

The key is to create moments that make your audience nod in recognition, as if you’ve written down their most embarrassing secrets.

Ask yourself: What are the awkward or painfully real moments in your life?

Then, figure out how you can turn them into comedy gold.

2. Embrace the Awkward

Some of the funniest and most memorable scenes in Insecure come from Issa’s awkward interactions.

Whether it’s bumbling through a breakup or navigating an uncomfortable work meeting, those cringe-worthy moments hit home because we’ve all been there.

Awkwardness is a treasure trove for dramedy.

It gives you room to build both tension and comedy.

Try incorporating situations where characters are forced to deal with uncomfortable truths, like being caught in a lie or running into an ex at the grocery store.

Awkwardness leads to vulnerability, and vulnerability leads to relatable drama.

Remember that humor doesn’t always have to be witty.

Sometimes, the most effective comedy comes from letting your characters flounder through life’s awkward messes, just like the rest of us.

3. Blend Drama and Comedy Seamlessly

What makes Insecure stand out is how effortlessly it shifts between drama and comedy.

One minute you’re laughing at Issa and her friends, and the next, you’re feeling the weight of a broken relationship.

It’s a delicate balance that makes the show so addictive.

When writing your dramedy, don’t force the humor.

Let it come naturally from the situations your characters find themselves in.

Maybe they’re dealing with a breakup, but something hilarious happens in the middle of the crying session — like a dog knocking over the wine bottle.

Life is messy, and the best dramedies reflect that.

Think about how real life often blends tears with laughter.

One doesn’t have to overshadow the other.

A truly great dramedy knows how to weave both emotions into a single, powerful narrative.

4. Create Multi-Dimensional Characters

No one on Insecure is one-dimensional.

Even side characters like Tiffany and Kelli have their own quirks and complexities.

Issa Rae excels at building characters who are layered and unpredictable, which is what makes them so relatable.

Your dramedy should have characters that feel like real people.

They shouldn’t just serve as punchlines or vehicles for drama.

Give them depth — like how Tiffany dealt with postpartum after having a baby and ran off.

Maybe your protagonist is a perfectionist at work but a complete disaster in their personal life.

Or perhaps they’re confident in social settings but struggle with self-doubt when they’re alone.

Great characters drive great stories.

Make sure each of your characters has something they want, something they fear, and something they’re willing to fight for.

That’s what will keep your audience invested.

5. Use Dialogue to Drive the Story

One of the standout features of Insecure is its witty, natural dialogue.

Conversations between Issa and her friends often feel like they could happen in real life, whether they’re texting, talking about relationships, or roasting each other.

Rae has a gift for making dialogue feel authentic while still pushing the story forward.

Your dramedy should use dialogue not just for laughs but to reveal character motivations, fears, and desires.

Think of dialogue as a tool to showcase your characters’ personalities.

Instead of exposition-heavy conversations, let the dialogue flow naturally, like friends chatting over brunch or co-workers gossiping during lunch.

But be mindful.

Good dialogue is more than banter.

Every line should serve a purpose, either deepening character relationships or pushing the plot along.

That’s what makes Insecure such a masterclass in writing.

6. Ground the Humor in Reality

While Insecure is hilarious, it never veers into slapstick or absurdity.

The humor is always grounded in real situations, like awkward sexual encounters or bad first dates.

It’s funny because it’s painfully true.

To emulate this in your dramedy, find the humor in everyday situations.

Maybe your character has a hilariously terrible job interview, or perhaps they’re trying to cook dinner for a date and accidentally set off the smoke alarm.

These are the kind of moments that will make your audience laugh out loud because they’ve probably experienced something similar.

The trick is to make sure your humor feels organic.

Avoid contrived jokes or forced punchlines.

Let the comedy arise from the natural absurdity of life, just like it does in Insecure.

7. Don’t Shy Away from Tough Topics

Insecure doesn’t just skate around serious issues — it tackles them head-on.

Whether it’s exploring gentrification in Los Angeles or discussing mental health, the show never hesitates to dive deep into tough conversations.

This is part of what makes it so powerful.

In your writing, don’t be afraid to explore difficult topics.

Drama comes from conflict, and conflict often arises from real-world issues.

Maybe your dramedy tackles themes of identity, relationships, or societal pressure.

The key is to handle these topics with sensitivity and depth while still allowing room for humor.

Issa Rae’s strength is in presenting these topics in a way that’s both thought-provoking and accessible.

You can do the same by giving your characters space to grapple with life’s challenges without losing the humor that makes your story engaging.

8. Let Characters Grow

One of the most satisfying things about Insecure is watching Issa evolve over the course of the series.

She’s not the same person she was in the first episode, and neither are her friends.

They make mistakes, learn from them, and sometimes fall back into old habits.

But they’re always growing.

Character growth is essential in a dramedy.

If your characters remain static, your audience will lose interest.

Allow your protagonist to change, even if it’s in small, subtle ways.

Maybe they learn to stand up for themselves, or perhaps they become more open to vulnerability.

Whatever the case, your characters should feel like they’ve undergone a journey by the end of the story.

The beauty of Insecure lies in its portrayal of imperfect, evolving characters.

That’s what keeps people watching, and it’s what will keep your readers hooked too.

9. Keep the Stakes Personal

In Insecure, the stakes are always personal.

The conflicts might not seem huge in the grand scheme of things, but they feel monumental to the characters.

Your dramedy should focus on personal stakes as well.

Maybe your protagonist isn’t trying to stop an alien invasion, but they are trying to mend a broken friendship or figure out their next career move.

These smaller, personal stakes often feel more relatable and impactful because they reflect the real struggles people face.

Don’t be afraid to dive deep into your character’s personal conflicts.

Sometimes the most compelling stories are the ones rooted in the everyday challenges we all face.

10. End with Hope (But Not Perfection)

One of the reasons Insecure resonates with so many viewers is that it doesn’t offer perfect, fairy-tale endings.

Relationships aren’t always neatly tied up, and characters don’t always get exactly what they want.

But there’s always a sense of hope and possibility at the end.

When writing your dramedy, aim for an ending that feels true to life.

Maybe everything doesn’t work out perfectly, but there’s a sense of growth and progress.

Your characters should be in a better place than where they started, even if they haven’t achieved all their goals.

Hope is the key to a satisfying dramedy ending.

It leaves the audience with a sense of possibility, even if not everything is wrapped up with a neat little bow.

Tying It All Together with Authenticity

Issa Rae’s Insecure works because it feels so real.

The characters are flawed, the humor is grounded, and the stakes are personal.

If you’re aiming to write a dramedy that resonates, these lessons are invaluable.

Keep it raw, embrace the awkward, and most importantly, let your characters be human.

Life is messy, and your writing should reflect that.

Whether you’re drawing from your own experiences or pulling from the absurdities of everyday life, a dramedy’s heart lies in its ability to make us laugh one minute and cry the next.

And if you can strike that balance, you’re well on your way to creating something as iconic as Insecure.

Happy writing!

Want More of This?

Enjoyed what you read? Want more? Hit that follow button and get a nonlinear dose of content on TV, movies, all things bookish, and whatever else that piques my interest or ruffles my tail feathers 😅

Or follow my other Medium page to learn how to make money online.

Check out my blog where I help authors with tips, tools, and resources to propel them to success on their author journey.

I also write about luxury travel.