With Insecure’s series finale, Issa Rae creates a world that’s difficult to leave

Insecure has always borrowed elements from its favorite genres. It can be a soap opera just as easily as it makes fun of dramatic soap opera tropes. It’s a funny hangout comedy and it’s a romantic comedy. Since Issa’s imaginary outbursts at We Got Y’all, the show has weaved elements of fantasy with a world where black women could be messy, horny hoes who make mistakes.

“Everything Gonna Be, Okay?!” highlights Insecure at its best: an intimate look at the moments in life when insecurity and doubt reign. When Issa is celebrating her 29th birthday in the show’s pilot, she’d been at the same job and in the same relationship for five years. Suddenly, a little voice in the mirror made Issa question everything about herself and her life.

Over the course of the show, we’ve watched Issa figure these things out. Issa has rarely had to rely on her mirror doppelgänger this season because she’s finally found some confidence. At the beginning of the finale, Issa wishes she could fast forward to the part of her life when everything is okay. What she doesn’t realize is that life does fast forward when you hit your stride. Just like five years with Lawrence and We Got Y’all flew by, “Everything Gonna Be, Okay?!” captures that same feeling. After Nathan and Lawrence’s fight, the episode cuts to Molly’s birthday a few weeks later. Then it’s Issa’s birthday. Suddenly, it’s a few months later and the girls are visiting Tiffany in Denver for her birthday.

As we get older, people get busy. We see each other less and grow apart. What ends up being important are the promises we keep to each other. Molly, Issa, Tiffany and Kelli promised to be there for each other’s birthdays. It’s a smart concept for a finale episode to center around that. It’s just as daring as season two’s finale “Hella Perspective.” In that episode, the timeline jumps between the same month from the perspectives of Molly, Issa, and Lawrence.

In this episode, Issa Rae’s script jumps between the rare personal moments we have with the people we love. Birthdays, weddings, deaths—these are the moments when it matters most for us to be there for each other. Molly and Issa have always been Insecure’s most important love story. Issa being there when Molly loses her mom and when she gets married is the triumph of their friendship. They made it work. Issa and Molly have finally found a way to give each other the security they were looking for without jealousy.

It didn’t always look like that would be the case. When Issa was sleeping on Daniel’s couch, it was hard to imagine she’d get the future she dreamed of with Lawrence. Hell, Molly squandered her chances with Sterling K. Brown. I figured she’d be headed towards some “I found happiness in my career”-standard trope professional black women are often stuck with. In fact, Insecure touched on this trope in its pilot when Issa spirals in a work meeting as a Frida recounts statistics on black women either struggling to get married, finding joy in their careers, or they fall into an abyss of nothingness. Molly and Issa have it all.

These girls were friends who could barely be honest with each other and now they quote each other’s quotes. As Kelli is famous for saying, “You know what that is? Growth.” And that’s what the show has always been about: two black women who got everything they wanted by evolving instead of settling. “Broken pussy” was Molly’s insecurity that Issa made fun of in the first season, in the finale they’ve reclaimed it in their own ways. The little voice in the mirror is gone.

Is it a satisfying ending? Absolutely. There are no cliffhangers. Even Nathan comes back to say he absolutely doesn’t regret ending things with Issa. We’ve loved these characters for a long time and it’s great to see them in the moments that matter. That being said, when the series is examined as a whole, it’s tough to say every moment really mattered. Did we need to spend so much time with Daniel’s sad beats in season three? Was season five really the time to dig into Nathan’s back story? “Everything Gonna Be, Okay?!” is an entire season in one episode and it just makes me wonder why that wasn’t the season we got.

I don’t think Nathan and Issa’s love story was so moving that it needed an entire season where they come back together. This season opened with a time jump to a year after Issa and Lawrence broke up, but would it have made a difference if we’d jumped to two years later and seen her relationship with Nasir instead of Nathan? I said last week’s penultimate episode suffered because it felt like the show was running out of time, but this week we get all the time in the world and it’s still not enough. Since there were a few time jumps, let’s break it down:

The episode starts right after Nathan and Lawrence’s fight. After the cold open, we jump to Molly’s birthday which is during scorpio season and it’s only a few weeks after Taurean was made partner (Insecure’s official Twitter account confirmed Molly and Issa’s signs, I suspect to help people follow the timeline in this episode). Also, Tiffany said she’d be back in town soon for Molly’s birthday in “Out, Okay?” Then we jump to Issa’s surprise party, which is during sagittarius season, so it’s only a few weeks later. It’s probably only been a few months when Nathan and Issa have their final goodbye.

From there, the timeline gets a little less clear. They’ve never celebrated Tiffany’s birthday on the show, but Molly’s mom dies before Kelli’s birthday. The first season ends with the girls going to Malibu for Kelli’s birthday, so about a season’s worth of life happens offscreen in this time. Eventually, it’s Molly’s birthday again and Issa is trading time with Taurean. Molly’s mother dying quickly sets off a string of events: Kelli gets pregnant. Issa and Lawrence get back together. Another year passes and Molly and Taurean get married. The episode ends on Issa’s birthday and Molly on her honeymoon (which means Molly got married right after her birthday?).

Logistically, everything makes sense! Even if I wasn’t a huge fan of Lawrence, I could accept Issa and Lawrence finding each other again years later. The biggest issue between them is that they could never give each other space. Issa loomed over all of Lawrence’s relationships and he was a gray area she never resolved. Yes, Issa cheated but she didn’t actually want to end things with Lawrence way back in season one. Showing us that the both of them went on to date other people and have their own lives makes it believable that they’d grow up enough to forget about the past. That’s how life really works. It isn’t a big romantic love triangle, but a series of choices. It’s deciding to be with the person you want to be with. It’s deciding to ignore that voice in the mirror because what does it really know? In the end, that’s what brings Issa and Lawrence together.

So why didn’t we spend more time watching these characters make more of those choices? Taurean and Molly are so charismatic together that you want to see how they navigated the loss of her mother. It would’ve been great to see Molly get her “engagement ring in the office” moment after the devastation it caused her in the first season. Of course, as viewers, it’ll never feel like enough but the final season has tried to place Issa at what feels like a crossroads. She thinks she only has two choices when it comes to her career. She thinks she has to decide between Nathan and Lawrence. Then “Everything Gonna Be, Okay?!” makes it clear that there is no crossroad. Issa just has to keep living life and trust that it’ll work out.

At the beginning of season five, Molly, Issa and Lawrence had to decide who they wanted to be and they had to make decisions that aligned with the images they created. They became the people they wanted to be and the last five seasons have been the journey to watch them get there. So, I can understand the pacing of this last season when it comes to their character development.

It’s harder to grasp when it comes to Tiffany and Kelli. Kelli has made only a few comments about how she hates kids, but it never seemed like enough for us to believe she didn’t want kids of her own some day. Especially after Simone was born and she loved being a godmother. Instead, the show says this change is because of her “near death” experience and the podcast she has that has been mentioned exactly four times in the series. Sadly, Kelli was never given the depth her character begged for and simply throwing a man and a baby at a character who didn’t prioritize those things doesn’t work.

Tiffany isn’t adjusting well to Denver and she’s pregnant again by the time of Molly’s wedding, but is that just Tiffany still trying to make things appear better than they seem? Derek and Tiffany are two characters who always hid their cracks and Tiffany telling her friends she’s miserable while putting on a brave face for Derek doesn’t seem great. Also her birthday will always be remembered as the day Molly’s mom died now.

I suppose it’s fair the biggest complaint anyone will have after this finale is that it’s just not enough (even though the episode was 40 minutes long). But, it’ll just never feel like we got enough time with these characters in this city. Issa Rae and the team behind Insecure crafted a world that’s difficult to leave. There was no perfect way to say goodbye, but “Everything Gonna Be, Okay” comes close.

Stray Observations

• This was the first episode written by Issa Rae since season four’s premiere “Lowkey Feelin’ Myself.” She certainly ended things on her terms.
• Okay, Lawrence Hive, you won. I still don’t buy the whole “Lawrence never fought for Issa” thing when the man tried to argue in a RiteAid though.
• They gave the Best Buy shirt a nod. We also said bye to We Got Y’all, The Dunes and Thug Yoda.
• Molly did not invite Dro to her wedding.
• Issa has a ring on so we have to assume Lawrence proposed. They have to know the fans wanted to see that!
• In season two, Molly’s mom says she’s saving money to pay for Molly’s wedding. I was sobbing when they showed her photo.
• Every shot of Los Angeles was beautiful, they really focused on saying goodbye to the city.
• I think people will be mad fan theories like Issa’s secret pregnancy or Tiffany’s affair never happened, but that was never the type of show Insecure was!
• Kelli leaves her office to work with Molly. I’m glad they created this story for her this season, but remember when Kelli was skeptical of working with black people when Molly was considering that firm originally? Again, it’s just sudden. Did we need to see Kelli becoming friends with the woman who works at Nathan’s shop when any of this other stuff would’ve been more interesting?
• We never got another update on Daniel.
• The final shot of the mirror was great.
• Well, this is my last Insecure review and the end of my time at The A.V. Club. It’s hard to believe I’m saying goodbye to this chapter, but I hope you’ve all had fun! I will never think I was too harsh on Lawrence, Issa supported him for two years! You can follow me on Twitter for TV opinions.