Created by and starring the iconic Issa Rae, Insecure has always felt less like a TV show and more like a survival guide for Black women navigating their late 20s and early 30s.

It’s that stretch of life where the choices are questionable, the men are confused, the jobs are great (even when the colleagues and bosses are not) and the friendships feel like contracts written in spirit, long before we arrived on this earth.

If you’ve watched Issa and her best friend Molly spiralling for the third time and found yourself whispering, “Damn… I’ve lived through a version of this,” then hello. Welcome. Pull up a chair. Grab some popcorn. Let us unpack.

When HBO’s Insecure landed in South Africa in 2018, I was wrapping up my own Season 2 of Me: Let’s Try Again, But With Some Edges This Time.

The pandemic softened all of us, forcing compassion for ourselves and others. I took a break from giving people a piece of my mind.

By 2024, I’d stepped into Season 3 of Me: Sure, I Can Bend Over Backwards For You…But What Have You Done For Me Lately?

And 2025 shaped up to be Season 4 of Me: You Know What? I’m Just Going To Say This — But Louder (For the People in the Back).

Thirteen years into marriage and I’m still learning how to communicate. I’ve become more honest, more transparent, more accepting of my partner’s quirks, and he of mine (though I’m still reinventing myself, so who knows what he’ll think this year).

Most days, we’re doing better than Issa and Lawrence. I’ll take the win.

Watching Insecure again reminded me of all I learnt about relationships, romantic and otherwise, from watching Issa’s misadventures and Molly’s meltdowns, set to the soundtrack of my 20s and 30s.

It was a decade-long montage of reinvention, mistakes, survival, and moments of “Oh, so THAT’S who I am.”

So here they are, the lessons I’m wrapping up into a small love-offering to all the versions of Me between 25 and 35, with honesty, prayer, and a little shade:

1. Thou Shall Speak Up, Even When It’s Hard (And You’d Rather Rap in the Mirror)

In Season 1, Issa knew two truths:

She was deeply unsatisfied.

She absolutely wasn’t going to admit that to anyone, not even to Molly.

By day, she was the unofficial spokesperson for all Black people at her nonprofit.

By night, she was dating Lawrence, a man who had occupied the couch for so long he might as well have been a built-in fixture. Instead of expressing her needs, she took them to the mirror.

I understood that more than I’d like to admit.

A few years into my marriage, I was holding the household together, a toddler on one hip, an infant on the other, and the family budget in my back pocket.

Meanwhile, my husband was building a start-up with unreliable income and no sleep.

Instead of saying, “Hey, I’m drowning,” I followed the Issa Blueprint:

Step 1: Don’t communicate.

Step 2: Act out.

Step 3: Wonder why things are falling apart.

Season 1 of Me: Was Basically Struggling. Sound familiar?

2. Thou Shall Stop “Finding Yourself”. You Are Not a Set of Keys.

After her breakup, Issa enters her reinvention era, the one with new hair, new habits, new hustle, and new disasters.

In my late 20s, I was wandering through life asking the dramatic question: “Who am I? And why is finding out so exhausting?”

Eventually, I realised I wasn’t lost. I was simply unfinished.

I stopped searching and started creating myself instead.

My 30s became my glow-up mixtape. I reinvented. I birthed new dreams. I even started an agribusiness — who was she?!

In my 40s, the reinvention is quieter. More assured. I know what I like, what I want, and where I’m going. When I show up as myself, I show up better in my relationship.

The tricky part? Getting my partner on the same page, especially when he’s still reading from the Season 1 script.

3. Thou Shall Not Date Potential — Ever Again

If Insecure taught us anything, it’s that dating a man’s “potential” is a quick path to heartbreak… and poverty.

Issa spent years loving Lawrence 1.0 — unemployed, depressed, and emotionally absent. The moment she leaves?

Suddenly God releases Lawrence 3.0 — moisturised, gainfully employed, gym-going, and glowing like he slept in affirmations.

And who benefited? Every woman except Issa. If you know, you know.

I’ve dated potential too. I’ve even encountered a hobosexual — the man who sees your stable life and whispers, “Wow… what a lovely place for ME to live.”

Empathy is beautiful. But empathy that depletes you is (self) betrayal.

The real flex is loving yourself enough to walk away — even when the chemistry is chemisting, the sex is memorable, and the fantasy sweet. The math will never math.

4. Thou Shall Never Lose Your Real Friendships Over Love

Forget Issa and Lawrence.

Forget Nathan.

Forget Daniel.

The true romance of Insecure is Issa and Molly.

They are mirrors for each other — awkward, polished, chaotic, ambitious, insecure, loving, messy, and real.

They drag each other. They uplift each other. They annoy and adore each other. They fall out and they fall back in.

Adult friendships are complicated, but they are sacred.

Watching Issa and Molly reminded me that friendships are the emotional pillars that hold us up while we rebuild the rubble of everything else.

Your romantic partner may love you deeply, but your best friend will love you and tell you you’re being stupid.

Friendships are the real love story.

Life is messy.

Relationships are chaotic.

Communication sometimes comes out in the form of mirror raps.

But if Issa Dee can fumble through her 20s and 30s and still find joy, love, and herself, then what’s stopping you?