Insecure Season 4: We just Got Their Best Season So Far

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One year, six months, and 13 days.

That is how long Issa Rae made us wait between seasons three and four of Insecure.

It was such a long time, and fans were getting antsy while Issa pursued other projects. 

Insecure Season 4

Luckily for us, it was definitely worth the wait! Issa gave us, arguably, the best season by far. The show is usually a comedy full of awkward moments, but this season we delved much deeper into the characters and their growth. Here are just a few reasons why it's a favorite.

Issa Got her Life Together (Mostly)

Let's be real. In the first couple of seasons, Issa was kind of a mess. 

She was in a dead-end job. She cheated on Lawrence. Then ended up sleeping on the couch of the guy with which she cheated. Sis had a 425 credit score. It was not looking good.

Microphone in Hand - Insecure

In season three, however, we started to see things turn around. She got a new job and her own apartment. She left Daniel and Lawrence behind (momentarily) and started seeing someone new. She then found her passion project.

After some encouragement from New Boo Nathan, Issa started to pursue throwing a block party showcasing Black talent in LA. We finally got to see this dream come to fruition, and it was a success (until that ending). Unfortunately for Issa, everyone in your circle won't support you. 

Issa and Molly Bump Heads

From the very beginning of the season, it seemed Issa and Molly were in a sort of cold war. As Issa told her in 4x03, "I feel like you've been coming for me."

And the attitude Molly had towards her for the majority of the season seemed to come out of nowhere. Why are you so bothered that Issa is working with Condola just because Condola's dating Lawrence now? This is business!

Friends - Insecure

In the past, Issa has always been available for Molly's every beck and call whenever she needed her. It seems as if Molly isn't used to Issa having something going on for herself. 

Molly knew how much this block party meant to Issa. When Schoolboy Q dropped out as headliner, Issa asked Molly to reach out to Andrew for a new headliner since he works at Live Nation. Molly refused, saying she didn't want to complicate her relationship with Andrew.

Sure, Molly, had a right to say no. But also, if this is your best friend, why wouldn't you want to help her? Even Andrew wondered himself why Molly just didn't ask him. 

Issa took matters into her own hands and just asked Nathan to ask Andrew. Andrew did it, and he didn't mind. And yet, Molly still had the nerve to get mad and cause a scene at the block party, which subsequently caused it to end. Did she WANT her best friend to fail?

Issa and Molly Block Party - Insecure

Issa eventually invited Molly to brunch to talk, and it seemed like things were getting back to normal. However, the episode ended with Molly suggesting they just grew apart. Issa agreed, and Molly got mad. I'm sorry, were you wanting Issa to beg? 

The girls had so much drama, and a lot of young women can relate. Sometimes you and your friends grow at different rates. Some friends struggle to balance friendships with their new relationship.

And sure enough, as soon as Molly and Andrew hit a rough patch, she went running back to Issa. If only that was a surprise.

Whether you're Team Issa or Team Molly in this war, we can all acknowledge their friendship is the true love story of this show. Their reunion was inevitable. Fingers crossed they actually work through their issues instead of sweeping them under the rug again.

Issa and Lawrence 2.0 - Insecure

Nathan Mystery Solved

In season three, Issa picked a young man up in her Lyft.

They went skinny dipping in a random person's backyard pool while taking a tour of LA. Eventually, they hooked up at Coachella. Thus began the romance of Nathan and Issa.

Nathan was a good guy who seemed really into Issa. That is until he ghosted her. He went missing out of nowhere for a month until he showed up in the season three finale, saying he was "in a bad place."

Many fans suspected it was mental illness, and it turns out that was exactly the case. In this season's penultimate episode, Nathan admits to Issa he didn't just disappear, but rather he received a bipolar diagnosis. 

Nathan's apology was sincere, and many viewers felt for him. Kendrick Sampson played the role well and really conveyed Nathan's agony at having lost Issa due to his illness.

Postpartum Depression

Nathan isn't the only one battling mental illness this season. At the beginning of the season, we see Tiffany and Derek had their baby. We soon learn it is not all happy endings after the baby arrives.

There were signs early on in the season that Tiffany was struggling. At Issa's block party, Derek was ready to get home to the baby, but Tiffany blew him off and decided to stay. This alone may not be a big deal, but it's obvious Tiffany was having issues.

Tiffany at a Party - Insecure

In the finale, Tiffany went missing, causing Issa, Molly, Kelly, and Derek to go on a goose chase. This storyline actually fell kind of flat, ending with them finding her in a hotel room. It would have been nice to see Tiffany's breakdown on screen, but not all mental illnesses present that way.

Lawrence and Issa 2.0

Lawrence and Issa have been through a lot over the years. They had a tumultuous breakup after Issa cheated on him with Daniel, dividing fans into #TeamLawrence and #TeamIssa.

Post-Condola, we see the two have a real conversation about their relationship and what went wrong. They both admitted what they did wrong and addressed the real problems they had. 

We got a blissful, albeit short-lived reunion. Lawrence got a new job, and they agreed to make the long-distance relationship work. It was all supposed to work out.

Reconciliation - Insecure

Then here comes Condolences. Sorry, Condola. Something had to have been up when she was so pressed to meet up and talk to Lawrence. Sure enough, the girl is pregnant, telling Lawrence he "can be as involved as [he] wants to."

The scene revealing the pregnancy was so well done. Executive Producer, Prentice Penny, said on Twitter, "I wanted Jay to be more empathetic to Issa and more angry with Condola." Jay Ellis definitely delivered.

The Social Media Conversation

One of the best things about watching Insecure is debating it on social media. The writers have done such a good job of portraying the black experience, which is why viewers take to their social media to talk about it for the whole week after a new episode airs.

It's not a black experience rooted in trauma, simply black people living their black lives. In a Q&A with Fast Company in 2016, Issa Rae said black people "don't get to just be boring" in most TV shows.

Speaking Engagement - Insecure

Issa Rae was completely right about that, and she has made excellent strides at making that change.

This season is further proof of that.

Over to you Fanatics! Do you think Issa will be a stepmom? Will she go back to Nathan? What's going to happen with Molly and Issa?

Share your thoughts about this season in the comments.

Berea Orange was a staff writer for TV Fanatic. She retired in November, 2020..

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Insecure Quotes

Molly: Whatchu got in here? Yes! A Capri-Sun! You know my heart.
Issa: Oh, no no no, girl--those are for passengers only.

We need to decide whether we're friends who don't have sex or acquaintances who just have sex. Because anything otherwise is a little muddy, and I need boundaries.