Still Talking

What changes when you watch the same show from a different place in your life? A conversation between sisters, years later.

October 9, 2026

There are some people you can ask a question and trust the answer will come back neat.

My sister is not one of those people.

Neither am I, which is probably why this works.

As I thought about this anniversary, I knew I wanted her voice somewhere inside it. Not because I needed somebody to agree with me about Insecure. We have never required agreement to keep a conversation going.

I wanted to know what she sees now.

Ten years is enough time for a television show to stay exactly where you left it while your own life does absolutely no such thing. You get older. Your relationships change. Your friendships change. The things you once thought were obvious become considerably less obvious. Sometimes the character who got on your nerves starts making a little more sense.

Sometimes they still get on your nerves.

So I asked my sister to think about Insecure with me.

“Ugh, you’re making me use my brain.”

She used it.

THEN

ME: Okay so you started watching Insecure in 2017, when we were both in a different stage of life 😩😩 and I didn’t watch it until 2020 (which was also another wild time 👀).

What did the show feel like to you back then? Not just what you liked about it, but did it feel like it was showing you something about your own life, friendships, relationships, or the age we were at that you weren’t really seeing anywhere else?

MY SISTER: Originally when I started watching Insecure in 2017, and at the time I was unhappy, but the show felt like something good…for once.

At the time, Insecure felt like a sense of understanding of something I never really felt like took up much space in my life, and that was…friendship.

But the relationship piece showed me a lot, particularly with Molly. One word, RELAX! 🤣

The show was the perfect symbol of friendship for me, almost like something I dreamed of and now had a visual illustration. It wasn’t my reality, so Insecure made it real.

I remember really resonating with Issa’s character the most at that point. I never thought I was going to pivot, but I did. Whew. 😮‍💨

Molly is a good example of what a few years can do to an opinion.

At one age, you watch her and decide she is doing entirely too much.

A few years later, life hands you some additional information.

Not enough to make every Molly decision defensible. Let’s be reasonable.

But enough to understand that sometimes two people can love each other and still be standing in completely different places. One is up while the other is trying to figure out what comes next. One is ready for something the other hasn’t reached yet.

Nothing about Issa and Molly’s friendship has changed on the screen.

What changed is the woman watching it.

And suddenly, “Molly is insufferable” has a little more room around it.

My sister said something else about the show that I keep coming back to. When she thinks about Insecure, she thinks about the transition itself: exiting your twenties and entering your thirties.

Friends moving away. Families growing. Finding your space.

Still wanting to do things the way you used to until life happens and you realize, I can’t.

She said clips from different episodes flash through her mind when she thinks about the show.

Not one relationship.

A whole stretch of becoming.

NOW

ME:You talked about Insecure being so much about that transition from your late 20s into your 30s. Now that we’re on the other side of some of those transitions, what do you understand differently? Is there a character, friendship, relationship, choice, or even a whole storyline where you look at it now and think, “Ohhhh, I get that differently now”? And what changed for you?

MY SISTER: I think I understand Molly’s and Issa’s relationship a little better. The younger I was, I thought Molly was insufferable, but the older I got I realized that they were just two friends in two different stages in their lives.

What happens when one is up and the other isn’t?

I understand the changes that happen in friendships. You get older, you have kids, priorities change, you change. How do you stay connected when you really grow up?

I remember being so sad when Tiffany moved. The older I got I realized that that is life. You don’t spend as much time as you’d like. Responsibilities take over and oh shit I gotta be an adult???? 🤯

But then I learned that if it can withstand, friendship grows WITH the changes in life. BUT it takes work; it isn’t miraculous.

“It takes work; it isn’t miraculous.”

Then everybody goes and gets a life.

People get married. Have babies. Move. Change jobs. Get tired. Become responsible for people who need dinner at an unreasonable hour every single night.

And somehow the friendship has to find somewhere to live inside all of that.

So I understand why Tiffany moving looks different to my sister now.

When you’re younger, somebody leaving can feel like the group is breaking apart. Then you get older and realize sometimes your people are going to build lives in places that aren’t near you.

The friendship doesn’t necessarily end.

But access changes.

And maybe growing up is partly learning that those aren’t the same thing.

US

ME:This is probably the one I’m most curious about: why do you think Insecure became one of our shows?

We’ve watched plenty of things, but we still randomly bring this one up, dissect somebody’s choices, compare something happening in real life to something that happened on the show, or go back to a conversation we’ve already had about it.

What do you think Insecure gave us to talk about that has lasted this long?

MY SISTER: think Insecure became our show because WE ARE THE CHARACTERS to an extent.

We have experienced just about everything: situations, incidents, bullshit, the cries, the laughs, confusion, and everything in between.

We lived it and lowkey lived it together.

My sister and I have known enough versions of each other by now to have our own language.

Some of it comes from things we lived through together. Some of it comes from stories one of us has told so many times the other could probably tell them herself. Some of it is a look. A joke. A phrase that stopped needing an explanation years ago.

And some of ours came from Insecure.

There are moments when Malibu is the only appropriate response.

Others call for We Did Say.

And that’s it.

No explanation. No context. Neither one of us needs it.

They sit alongside everything else we’ve collected over the years—the references, jokes, stories and memories that somehow became part of the way we know each other.

We’ve known each other through enough versions by now to know that none of them lasts forever. Life changes. We change. What we need from each other changes too.

But there is something about having a person who knew the version before this one.

Someone who remembers what you were worried about then. What you thought you wanted. What you swore you would never do. Someone who can look at the life you have now and remember when it was still something you were trying to figure out.

Maybe that’s part of why Insecure became ours.

We got to watch these women grow up while we were busy doing some growing of our own.

And through all of it, we had each other.

MY SISTER: “Insecure is the show that reminds me that I never have to do it alone as long as I have you.”