The Show Ended. The Conversations Didn’t.

Ten Years of Insecure, and Why We’re Still Talking About It

October 9, 2026

Every few months, for no particular reason, I get the urge to watch Insecure.

Not a clip. Not a favorite episode.

I want to be back in it.

So I’ll text my sister something like, I think it’s time to watch Insecure again.

And she knows exactly what I mean.

The question isn’t whether we’re watching. It’s where we’re starting.

Because we’re not necessarily going back to season one. We might start somewhere in season three. There might be one episode I want to see and then, three episodes later, I’m still sitting there. Sometimes one of us remembers a scene differently and that’s enough reason to go find it.

My fiancé thinks this is hilarious.

At this point, he’s probably wondering how many times two people can watch the same show and still have this much to say about it.

A lot, apparently.

Because every time I go back, I find something else.

And the funniest part about Insecure becoming one of those shows for me is that I was late.

Like, late late.

I remember everybody talking about it on Twitter before I had ever seen an episode.

Black Twitter, specifically.

What a time.

I knew there was an Issa. I knew there was a Lawrence. I knew people had feelings about these people because every week my timeline would turn into a debate I did not understand. There were memes I had no context for, screenshots from scenes I hadn’t seen, people arguing over who was wrong like these were their actual friends.

And I would just scroll right past it.

I don’t even know why.

Then 2020 happened.

I was home, like everybody else, looking for something to watch, and at some point I finally started Insecure.

Almost immediately I had one thought:

Why was I not watching this when everybody else was watching this?

Because now I understood.

Lawrence on that couch. Issa in that mirror. Molly being Molly.

All these people I had been seeing on my timeline for years suddenly made sense.

My sister had already been watching, so while I was making my way through those first four seasons, every now and then I’d call her.

I would have a question.

Or an opinion.

Usually an opinion.

Sometimes she’d answer me. Sometimes she’d tell me to keep watching. Sometimes she’d tell me to call her when I got to a certain part because whatever I was saying was clearly missing several pieces of information she was not about to give me.

And I kept watching.

Four seasons, one after another.

By the time I caught up, I finally got to do what I had missed all those years before: watch Insecure with everybody else.

For those final two seasons, I was there.

No catching up. No old Twitter arguments telling me something had happened before I got there. I got the episode and then the conversation.

And now, five years after the finale, I still go back.

Which is how you know a show has really gotten you.

The finale can air. Everybody can go home.

And somehow you’re still in their business.

It’s funny what stays with you.

Not always the big moments either.

Sometimes it’s one look. One line. Something Kelli said. One of Issa’s songs that had no business being as funny as it was. Sometimes it’s a word that escaped the show and became shorthand in your own life. Sometimes it’s a scene you remember one way, only to watch it years later and realize you understand everybody in the room a little differently.

That’s the fun of going back.

The big moments tell me what Insecure was about.

The little ones remind me what it felt like to love it.

And the more I return to it, the more I think Insecure was a love story.

Actually, it was a whole bunch of them.

That’s what made it so good.

You could come for Issa and Lawrence—and believe me, I have thoughts—but love was everywhere in this show.

It was Molly wanting it and sometimes getting in her own way before finding something that fit. Tiffany and Derek building a life that wasn’t nearly as effortless as it could look from the outside. Daniel belonging to one part of Issa’s life. Nathan belonging to another. Issa and Molly having to figure out whether a friendship could survive the people they were becoming.

And then there was Los Angeles.

Insecure loved that city.

You could see it.

Not some generic Los Angeles that could have been anywhere with palm trees. South L.A. had texture. Neighborhoods mattered. Restaurants mattered. Streets mattered. The city wasn’t scenery sitting politely behind the characters. It was part of their lives.

And I loved looking at this show.

I mean that literally.

The light. The color. The apartments. The hair. The clothes.

I watched the fashion almost as closely as I watched the people. Sometimes I loved what Issa had on. Sometimes I loved what Molly had on.

And then Molly would show up in those white boots.

I hated those boots.

Every time.

I have had years to reconsider this position.

I have not.

But even that is part of remembering Insecure for me.

There was always something to look at. An apartment could tell you where somebody was in her life. The clothes could tell you something before the person wearing them said a word. The city could feel intimate one minute and enormous the next. Even nighttime looked like somebody had thought about exactly how we should see these people moving through it.

The music knew where we were too.

It never felt like something dropped underneath a scene because silence needed filling. It belonged to the storytelling. Sometimes it carried the mood. Sometimes it introduced you to somebody you hadn’t heard before. Sometimes it arrived at exactly the right moment and made the scene impossible to remember without it.

All of those choices added up.

The clothes. The color. The skin. The awkward silences. The mirror raps. The parties. The apartments. The city at night.

Blackness was everywhere without the show having to stop and translate it.

It could just be.

Beautiful. Petty. Stylish. Awkward. Selfish. Ambitious. Funny. Wrong.

Human.

That’s part of what I mean when I call Insecure a love story. Love wasn’t sitting in one relationship waiting for us to find it.

It was all over the place.

And underneath all of those love stories, there was Issa learning to love her own life.

Not the one she thought she should have by a certain age.

Hers.

The messy one.

The one she kept changing.

I found the show at a time when a lot was changing in my own life. More than I knew how to make sense of then. Some things had ended. Other things were finding their way back. Work looked completely different. The whole world looked completely different.

And then here came Issa.

Uncertain. Funny. Awkward. Capable of making a decision that had me talking to the television like she could hear me.

Trying to figure out love and work and friendship and what exactly she was supposed to be doing with this life of hers.

I don’t think I realized then how much of myself I saw in her.

I’ve never really said that out loud.

But I did.

I do.

And now I don’t watch the show from the same place I watched it in 2020.

I’ve caught up to things I didn’t understand the first time. I’ve changed my mind about people. I’ve changed my mind about choices. Things that once looked simple don’t always look simple anymore.

There are characters I have more patience for now. Others I have less.

That’s what happens when you keep returning to a story while your own life keeps moving.

Eventually, you bring a different person back with you.

The characters were allowed to keep moving too.

We watched careers change, relationships end and begin again, friendships get tested, people become parents, lose parents, move away, come home, fall apart and figure out what came next.

Nobody had to know who they were before we were allowed to care about them.

People got to make bad decisions without those decisions becoming their permanent identities. Love could arrive at the wrong time. Friendship could fracture and find another shape. Growing up could look less like finally getting everything right and more like learning what was worth returning to.

Nobody had to be one thing.

And Insecure had time to let that happen.

Five seasons gave these people room to make a mess, live in it for a while and become somebody on the other side of it.

Rae has said she knew early on that this was a five-season story.

Then Insecure got to finish.

That matters too.

Black television has given us characters people are still talking about decades later. Scenes we recognize almost immediately. Shows that became part of the language inside Black homes and friendships.

It has also given us stories that disappeared before the people who loved them were ready. Stories that never got the luxury of deciding exactly how they wanted to leave us.

Insecure did.

And during those five seasons, it added something distinctly its own to the larger story of Black television.

These people didn’t have to represent all Black people.

That gave them room.

Issa could be awkward. Molly could be difficult. Lawrence could get things wrong. Kelli could be completely out of pocket. They could be ambitious, selfish, loving, petty, uncertain, successful, heartbroken, hilarious.

Sometimes they could just be wrong.

The show could care deeply about Black culture without turning Black culture into an exhibit.

It could assume we knew.

The hair didn’t need a footnote. Neither did the language, the music, the parties, the neighborhoods, the friendships or the thousand little things that made the world recognizable.

You could just walk in.

And for five seasons, we did.

FROM THE EDITOR

Before The Living Room Had a Name

There is one other reason this anniversary feels personal.

Before The Living Room had a name, I told my sister I wanted to do something like what Issa was doing with The Blocc.

I didn’t mean I wanted to make The Blocc. And I didn’t mean I wanted to make Insecure.

I recognized something in what she was creating.

I’m drawn to people who know how to build a world—to the details that make an idea feel lived in and make people want to enter it and stay awhile.

I had spent seasons watching Insecure do that through story.

Something about that stayed with me.

My own idea would change names and shapes before it became The Living Room.

Not my version of The Blocc.

Mine.

Insecure didn’t hand me a blueprint.

But seeing somebody make the thing she believed should exist made it easier to imagine that I could make mine too.

And now, ten years after Insecure premiered, I’m sitting inside something I once didn’t have a name for, making room in it to celebrate a show that helped me imagine building in the first place.

There are plenty of reasons to talk about what Insecure meant to television. To Black storytelling. To Los Angeles. To music. To the people whose work we discovered because of it.

All of that matters.

But sometimes I go back for a much simpler reason.

I miss them.

Not just the people we met at the beginning.

I miss who they became.

I miss the parts in between—the years when they were getting things wrong, changing their minds, losing things, finding other things, falling in love, growing up.

I miss the apartments and the birthdays and the arguments that should have ended twenty minutes earlier. I miss the clothes I loved and, apparently, the ones I hated enough to still be talking about ten years later.

I miss Los Angeles glowing in the background.

I miss the music coming in at exactly the right moment.

I miss the whole world of it.

Knowing where everybody ends up doesn’t ruin the beginning for me.

It makes me want to see it again.

Because when I go back now, I’m not only watching who these people were.

I know who they’re going to become.

I know some of the things they’re certain about won’t last. Some of the people they think they’ve lost will find their way back. Some relationships will change shape completely. There are losses they can’t see coming yet, and whole lives waiting for them on the other side of decisions they haven’t even made.

They don’t know any of that yet.

We do.

And there’s something about knowing how much life is waiting for people who can’t see it yet that gets me every time.

Maybe because none of us can.

So every few months, for no particular reason, I pick up my phone.

I think it’s time to watch Insecure.

My sister knows exactly what I mean.

Where are we starting?

I don’t know. How long do we feel like waiting for Lawrence to finally get off that damn couch?