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5 Takeaways: Insecure Season 4

June 22, 2020
4 min read time

Issa Rae’s Insecure, now in its fourth season, has truly hit its stride. Rae is excellent at creating characters you root for even when they’re in the wrong—or too busy making mistakes to realize how they might be breaking someone else’s heart. While previous seasons had viewers on the edge of their seats rooting for the right man for Issa (Lawrence vs Nathan), this season was all about the womance (and the deterioration thereof) between Issa and Molly. This examination of the girl-ationship is perhaps why season four of Insecure felt so special.

Here are Five Takeaways from this season to help screenwriters craft an infinitely watchable relationship to sustain a series past season one.

Warning: Spoilers ahead!


  1. Establishing Fatal Flaws. No one is perfect, especially Issa and Molly this season. Afterall, Rae created the show from her original web series, Awkward Black Girl. She does an excellent job reminding us of just what exactly gets under the skin of these two BFFs when Molly says Issa always attracts drama, and she’s right. As the season opens, Issa is doing her best to court friendship with Condola, who is helping her secure vendors for Issa’s upcoming Block Party. It’s soon revealed Condola is dating Lawrence, Issa’s long-time ex. On the other hand, Molly’s flaw is she always has to be right, hindering her ability to truly be vulnerable in her relationship with new beau Andrew. These fatal flaws are also what these two women love about each other. In previous seasons, Molly was always there to give advice when Issa found herself surrounded by drama, and Issa has always admired that Molly is a woman who gets what she wants. But in this season, their fatal flaws help fuel conflict. 
  1. Create Obstacles to How Things Used to Be. Season four is definitely about evolution for both Molly and Issa. On multiple occasions, they realize it’s not so easy to always drop everything and do a Self-Care Sunday or pick up the phone and talk for hours. But maybe this is a good thing, as both see personal strides in career and love. Issa’s burgeoning new career as an event planner is taking off, and Molly has a new relationship with Andrew. Unlike a traditional sitcom, these dynamic and layered women are growing and changing. However, thematically, they’re also left to wonder—is their long-time friendship still serving their busy lives? The thematic question deepens when Molly refuses to ask Andrew to help Issa secure talent for a big event at Issa’s request. The rift between the two deepens even more, and, as any good screenwriter knows, that rift is going to turn into an earthquake of disruption. 
  1. A Fight to End All Fights. Rae carefully plants the seed of conflict with Issa’s Block Party event and big ask of Molly’s music industry beau, Andrew. When Molly refuses to ask Andrew for help, Issa goes to Andrew’s roommate Nathan and asks for a connect to secure a big talent name for her Block Party. Andrew is happy to help, and ensures Issa can secure her big Block Party act, but neglects to inform Molly. When Molly discovers what all went down—while at the Block Party—the pair have it out in public. It’s the lowest moment of the season. A fight to end all fights. It’s the perfect high-low: Issa finally gets a professional triumph with the Block Party success, but she also gets knocked down by her very best friend. It’s the kind of fight that you wonder if the pair can recover from, and for a moment, you even wonder who to root for, as neither has done right by the other. 
  1. False Amends. After the fallout, Issa reaches out to make amends and at Andrew’s urgings, Molly agrees to meet for brunch. The women are cordial, but something is still off. This is a classic misdirection in screenwriting. A moment of calm before another likely storm. It’s a Band-Aid when some major gauze, therapy and conflict-resolution is needed. But it’s also a great device to keep viewers watching. Fans are still left to wonder what will become of this relationship that has so deeply anchored the show. This beautiful female friendship that made us tune in to know, life really is better with a best friend by your side. The Band-Aid is ripped off when Issa helps Nathan move out of Andrew’s place. Andrew invites Nathan and Issa to stay and celebrate with himself and Molly. But then Issa gets a text from Molly meant for Andrew that reads, “See, I’m really trying with her…” Issa is crushed. 
  1. Thematic Pay-Off. Rae did an excellent job of threading the girl-ationship throughout this season. She teased the rift that would serve as story engine in the first scene of the first episode when Issa confesses on the phone to a mystery caller,“I don’t really fuck with Molly anymore.” Rae then closed the season (no spoiler on the final episode) with excellent dramatic pay-off while still giving viewers a cliff-hanger on the Molly/Issa saga, letting us know there will undoubtedly be another season to indulge in. 

Final Takeaway:  If you are writing or studying the womance, there is possibly no better current study of the ups and downs of friendship love than this season of Insecure. Rae has written two nuanced and complete characters with Molly and Issa, who are both ready to open their hearts and break each others’, creating infinitely watchable television. So set the bromances aside and embrace the complicated relationship of female friendship.  


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