It's Almost Over, Okay?! Look Back At Our Fave 'Insecure' Moments Ahead of The Series Finale

By Rivea Ruff · Updated April 29, 2022

After five seasons of explosive drama and relatable hilarity, Insecure is finally giving final closure to the story of Issa, Molly, Kelly, and Tiffany.

Since 2016, the HBO drama-comedy has been a roller coaster ride of relationship lows and professional highs as the ladies embarked on their second coming-of-age; transitioning out of their fun fledgling late 20’s into their life-path-defining early 30’s. Our protagonist Issa Dee, in particular, has spent each season discovering who she is and what she truly wants through a series of major mistakes, bold decisions, and of course, bathroom mirror freestyles.

As we left off in the penultimate episode, each of the women are at a crossroads in their lives. Kelly is looking at making estate planning for Black families a key component of her financial advising career. Tiffany is preparing to uproot her life and relocate to Denver for her husband’s job. Molly is excelling at work and may have finally found a healthy relationship that she’s mentally and emotionally prepared for. Issa’s cultural event business is taking off just as she is on the crux of getting extra serious with Nathan…when new father Lawrence pops back up to let her know he’s still in love and needs her back in his life.

It’s about to get messy, okay?! But while we wait to see what Prentice Penny and Issa Rae have in store for us with Sunday’s grand finale, let’s take a look back at the moments that had us shook, seeing ourselves, and hella-hooked to our screens every weekend.

Insecure, you will truly be missed!

01

Broken P*ssy – (Season 1, Ep. 1: Insecure AF)

In the series premiere episode, we’re introduced to our awkward and unsure protagonist Issa, in the midst of celebrating her birthday (which her out-of-work couch potato boyfriend Lawrence apparently forgot all about) with her longtime best friend Molly. When she runs into her high school crush-turned music producer Daniel, she takes the opportunity to impress by putting her private mirror freestyle skills to work, hitting the open mic with an impromptu song based on her bestie’s tragic dating life. Sure it upset her homegirl for a moment, but as the season unfolds, we see that the bold move clearly had its desired effect…

02

Lawrence Claps Back (Season 1, Ep. 8: Broken AF)

Just as things seem to be calming down in the explosive first season, we end off with a banger of a cliffhanger. After Issa’s infidelity comes to light, she and Lawrence are in a state of limbo while he debates his next move. Understandably angry and “done” with Issa, he sleeps on a friend’s couch for a few days while ignoring Issa’s pleas to talk. A trip to the strip club makes him realize he misses her, and he calls her and tells her as much. Taking this as a cue, Issa rushes back from a girls’ trip to Malibu to reunite with her man…only to find the apartment cleared out and Lawrence nowhere to be found. Instead, he’s across town…um, releasing his frustrations with the pretty bank teller who’s been giving him eyes all season.

03

Molly Gets Entangled (Season 2, Ep. 5: Hella Shook)

Molly reconnects with her childhood friend Alejandro (Dro, for short), who’s married yet suspiciously flirtatious. He reveals to Molly that he and his wife have an open marriage arrangement and suggests that since they clearly have such great chemistry, he and Molly should turn their platonic relationship sexual. Initially somewhat offended, Molly refuses. She wants the type of love and affection her parents have always had. But when she discovers her own father’s old infidelity at her parents’ 35th anniversary party, she casts old values aside and decides to take a leap…straight into bed with Dro.

04

What Could Have Been (Season 2, Ep. 8: Hella Perspective)

Forced out of her apartment due to rapid gentrification and rent increases, Issa hurriedly gets rid of furniture while deciphering where she’ll go. However, she can’t seem to bring herself to sell the blue velvet couch she and Lawrence picked out together. In an effort to let Lawrence take the couch with contactless delivery, Issa invites him over to the empty apartment at a time she won’t be around. But to her surprise, Lawrence waits to meet up with her. They end up having a frank conversation about where their relationship went wrong, take accountability for each of their parts in it, and acknowledge the love they still have for each other (and likely always will). As they peacefully part ways, Issa has a poignant flash of what their life could have been like if things had never gone left – a proposal, a marriage, and an adorable baby all experienced together on that same sofa.

05

Molly Forgets To Flip Her Code Switch (Season 3, Ep. 3: Fresh-Like)

After feeling underappreciated and underpaid at the predominately white male law firm she worked at previously, Molly finally gets a fresh opportunity at a Black firm with plenty of women at the helm. But when resources and facilities aren’t quite at the level she’s used to, Molly is very vocal about the difference in standards. What she thinks are offhand comments are taken by her co-workers as condescending whines, and she makes a poor first impression at her new opportunity – much like the loud and boisterous DaDa did during Season 1.

06

The Beychella Ferris Wheel (Season 3, Ep. 5: High-Like)

All the ladies are at crossroads…but it’s nothing a few recreational drugs can’t assist with. While out in Palm Springs to catch Beyoncé’s Coachella performance, the ladies connect with Issa’s Lyft customer-turned-new potential bae Nathan and his crew of friends at a day party. Once the edibles and pills start flowing, the inhibitions come down. Issa and Nathan separate from the crew and decide to take a (rather momentous) ride on the famous Coachella Ferris wheel. Nathan is suddenly looking like a promising possibility to toss her “ho-tation” aside…

07

Molly & Issa Square Up (Season 4, Ep. 5: Lowkey Movin’ On)

After four episodes of palpable tension, sideways comments, and general frienemy pettiness, things boil over for these besties(?). Things seemed to begin to cool off as Issa’s big block party turned into a quick success and Molly finally settled comfortably into her relationship with Andrew…but a perceived betrayal discovered in the 11th hour nearly brings the homegirls to all-out blows. Let the #TeamMolly vs. #TeamIssa debate rekindle.

08

They Want That Old Thing Back (Season 4, Ep. 8: Lowkey Happy)

Issa and Lawrence reconnect for dinner. The two have finally gotten to a place where they can discuss their past with frank openness without getting upset, and we finally get a glimpse of what these two were like when they were happy and comfortable together. A few drinks, a few honest apologies, a couple of open realizations over a long walk through the arts district, and these two seem primed to rekindle things – especially after Issa makes her intentions clear and spends the night. Meanwhile, Lawrence is blowing off calls from his most recent ex (and Issa’s former associate) Condola. All leading up to…

09

Our ‘Condolences’ (Season 4, Ep. 10: Lowkey Lost)

The moment that dashed Issa and Lawrence’s perfect second chance at love once and for all. Lawrence’s very recent ex Condola (also known as Condolences, Controlla, Condoleeza, Conundrum, Condominium, Conspiracy, Canola Oil, or Con-Artist, depending on which fans you consult) has been blowing up his phone in the background of the action for several episodes. While we assume it’s just to get some sort of closure, it turns out that she actually just wanted to meet face to face to drop the bombshell that she’s pregnant and has decided to raise the child – on her own, if need be. This naturally throws a big-time monkey wrench into any plans Lawrence may have to reconcile with Issa.

10

Coparenting, Okay?! (Season 5, Ep. 3: Pressure, Okay?!)

Condola’s declaration to Lawrence that he can be just as involved or not as he pleases in their baby’s life is going just about as well as fans guessed it would. With Lawrence having moved to San Fransisco for a high-powered tech job, he’s been pretty much on a “need-to-know” basis with Condola via text her entire pregnancy. But once he gets word that his son has arrived, he’s suddenly emboldened to be an active participant and thrust into the awkward situation of figuring out fatherhood from 350 miles away.

11

“Eff them kids!” (Season 5, Ep. 6: Tired, Okay?!)

While Issa is at the hospital helping out Molly during her mother’s stroke, she runs into a seemingly reconciled Lawrence and Condola, taking their son to a doctor’s visit in another wing. She approaches them, says hello, asks that they pretend that the situation isn’t super-awkward, and even holds their child…before launching him like a free-throw shot and declaring “F*ck them kids!” She karate kicks Condola into a nearby laundry cart and cracks up laughing, bucking at Lawrence on her way back down the hallway. But relax…it’s only one of Issa’s famous daydreams.

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12

Waiting to Exhale-Like (Season 5, Ep. 7: Chillin’, Okay?!)

Tiffany, Molly, Issa, and Kelly have a night full of fun hijinks and true sisterhood when girls’ night out turns into an honest evening in for the four friends. Tiffany reveals that she and her family are moving to Denver and the ladies tearfully embrace upon realizing how much their lives and bond are about to change. We get some serious Robin, Bernadine, Savannah and Gloria vibes as they dance and laugh together around Issa’s living space, a visual homage to Waiting to Exhale.

13

(Fist) Fighting for Love (Season 5, Ep. 9: Out, Okay?!)

Lawrence debates skipping Tiffany and Derek’s going away bash with the knowledge that Issa will likely be in attendance. When his friend Jared points out that all should be water under the bridge since he didn’t bother to fight for Issa, Lawrence suddenly has a battery in his back to finally profess his feelings. With his heart (literally) on his sleeve in that Comme des Garçons sweater, Lawrence is dismayed to see Issa at the event with another man, whom he promptly takes thinly-veiled digs at. Despite all this, he pulls Issa aside to confront her with his love. In steps Issa’s boyfriend Nathan. With Lawrence refusing to back down, the two cause a HUGE scene at the swanky affair, having to be physically blocked from coming to blows.