It’s back! Don’t act like you aren’t excited by it. It’s been about a year and half since we had a new episode of “Insecure,” and as this crazy world only seems to get crazier, it couldn’t have come at a better time. 

Let’s get to recapping! 

We’ll tackle Episode #1 of Season #5 (the final season), which had its debut on HBO this past Sunday, by going through each of the larger themes we think will play out this season. 

The Friend Group

As a friend group, the team appears to be strong, all deciding to attend their 10-year reunion at Stanford. Now, I’ll admit…I missed the part in the series where they explained that they are all college friends from Stanford, but I ain’t mad at it. More importantly, what it denoted to me is that this group’s roots go deep. As someone who has been out of college for a minute, I can attest to just how hard it is to maintain those friendships over a period of 10 years, especially when they originate at an age when many of us don’t understand and value that college is probably one of the last times in your life that you will l be immersed in an entirely new group of people that are open, and practically necessitated, to befriending new people. 

But alas, the group has made it here…back to campus. They’re all friends, and they are all talking. Even Molly and Issa are cool and seem to be cordial and friendly, yet also awkward around one another. Tiffany brought her boo, and she seems to be past her postpartum period as her and her husband seem to be at ease with their decision to leave their newborn at home. Kelli is as loud as ever until she realizes that the reunion organizers pronounce her dead in the reunion pamphlet. At first, Kelli sees this as an opportunity to have fun and pretend to be somebody else. But as she realizes people have not so fond memories of her, she begins to feel like no one takes her seriously and that she’s been leading a life that no one will remember. As a result, the crew ends up throwing her a fake funeral in which each of Kelli’s friends give pretend eulogies that profess just how profound and vital a life Kelli has led. 

Issa’s Reckoning with Growth

Over the first four seasons, Issa has definitely gone through different periods of growth. In the first season, a lot of it was around outgrowing people (Lawrence) and leveling up at work. The second season was about taking care of herself and meeting new people. The third season was a lot about growing as a friend group and keeping her goals together. Season 4 took it back to professional growth, as she followed quitting her job by throwing the infamous block party. 

In Season 5, Issa’s growth appears to be about “not going back”. In my mind, it’s as if Issa has decided that she needs to stop growing in the way that she has. Meaning that she has made enough foolish mistakes, and she has learned more than enough from making those mistakes, so she shouldn’t have to keep making the same mistakes over and over again to grow. Thus, it’s interesting that the episode kicks off with Issa talking to her collegiate self in the mirror, going over who she was then and who she has become now. Naturally, her former self takes some jabs at Issa’s inability to achieve all of her wildest dreams. But Issa’s current self looks healthy, has beautiful teeth–thanks to her old self’s braces, and she’s a big-time entrepreneur who will be on a panel about entrepreneurship during the reunion. All and all, Issa realizes she has grown but recognizes there is still work to be done. 

Speaking of the panel, Issa sits alongside some other alums who are also entrepreneurs (a filmmaker, an art director, and a start-up founder). Throughout most of the panel, Issa is trying to figure out how to get applause or laughs from the crowd and fails miserably as the other panelists seem to get her desired response with half the effort. But when a question comes up about “how you as an entrepreneur know when you are on the right track”, the other panelists are extremely confident in their answers and suggest that they knew they were on to something after some super evident point in their business’s life. However, Issa admits, publicly, that she doesn’t know if she’s on the right track. That she might be making a mistake. And that she may regret ever coming to start a company of her own. While this naturally depresses the crowd, it’s profound that Issa has suddenly realized the gravity of her decision to go on this path. Will she continue on it or give it up now that she sees the risk? 

Independent Molly 

Molly’s arrival at the reunion is with a thud, as she quickly iterates that she needs to take care of herself and be present at the reunion as she tries to recover from her boyfriend-breakup and all of the issues she has had at work. She has come to the realization that she is always doing too much, and now she just wants to do what’s right for her, and not always worry about what’s ahead. She’s also trying not to be too needy. But Molly is quickly tested when some of her old college friends start trying to hook her up with an old, now divorced, flame from college. For a minute, Molly is extremely tempted to pursue the guy as he keeps reaching out to her, but after a quick talk with Issa, she gathers herself and realizes that it’s that overly eager mindset that has gotten her in trouble in the past. Independent Molly ends up not going after the guy and instead just enjoys the company of her friends. 

Molly and Issa 

In front of the group, Issa and Molly are on their best, yet awkward, behavior. However, at one point, Molly turns to Kelli to ask how Kelli and Tiffany repaired their friendship. Kelli admits that it was hard work, but that she simply did her best to laugh at every one of Tiffany’s jokes and to support her in every way–even helping her grow her hair! Molly takes that to heart and starts trying to be the friend to Issa that she needs Issa to be to her. 

As Molly and Issa walk through the campus, grab lunch, and steal a couple of beers, they both reminisce about how fearless they used to be, how much fun they used to have, and how often they have been there for one another–including Molly going off on some lady while riding the bus off of Stanford’s campus. At first, the reminiscing is quite awkward as they’re trying to figure out how to be around one another. In fact, they almost seemingly come to the conclusion that things just might be awkward for a long time. 

However, on a trip to Oakland to relive some of their Reggae dancing days, the entire crew brings along an old, ratchet friend. Molly, Issa, and the friend get out of the car to get some liquor for the party. When they come out, they begin to get robbed at gunpoint. The ladies begin giving the thief all of their valuables. Issa is a little bit offended when the thief takes Molly’s heels but lets Issa keep her shoes. At one point though, the thief mentions the ratchet lady’s name and exposes that she’s in on the robbery. The ratchet lady, who again is their friend from college, snuggles up next to the thief and begins to ask Molly and Issa to come up off their stuff. After giving it all up, Issa and Molly walk back to the car where an unsuspecting Kelli and Tiffany ask them what happened to the liquor. Molly and Issa then look at each other, grimace, and then just burst out laughing and recalling moments during the robbery where each of them was scared out of their mind–causing them to laugh even harder. After all the pain they’ve been through over the past season or two, it appears this moment was what they needed to remember who really has their back in life and who they want to be in moments like that with. Friends forever again? 

Molly and Lawrence 

When we last left Lawrence and Issa, Lawrence was figuring out whether to take a job in San Francisco, rekindling his relationship with Issa, and of course, finding out that his old girlfriend, Condola, is now pregnant. So when Lawrence picks Issa up from the airport and they exchange a very close hug, we’re surprised that upon dropping her off at home, Issa breaks up with him, seemingly not ready to deal with the emotional baggage of being with Lawrence when he has a new baby on the way. Perhaps it was Issa realizing that she no longer wants to make the same mistakes when talking to herself in the mirror that caused her to dump him. Whatever it was, I’m sure this isn’t the last we’ve seen of Lawrence and Issa’s relationship. 

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