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Insecure AF.
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Insecure is a 2016 HBO series created by Issa Rae and Larry Wilmore, based (partially) on the former's web series Misadventures of Awkward Black Girl.

Rae stars as Issa, a young woman working for a nonprofit organization whose looming thirtieth birthday prompts her to start rethinking her life choices, including whether or not she should dump her deadbeat boyfriend Lawrence.

Issa's best friend Molly, however, seems to have it all together — except when it comes to romance. Despite her job as a successful lawyer, she can't seem to find a man worth keeping.

Insecure has received lots of acclaim since its debut, thanks in part to its nuanced portrayals of blackness and female friendship, as well as carrying over all the aspects of Awkward Black Girl that made it work with viewers.

It was announced in 2021 that the fifth season would be its last. It officially ended on December 26th that same year.

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Troped As Fuck:

  • A Mistake Is Born:
    • A light example, but Derek admits to Lawrence that he and Tiffany weren't planning on having a child for another few years before Simone was born. They love her dearly, nonetheless.
    • Even Issa's mother admits that both she and Ahmal were unintentional pregnancies, but they're also the best things that ever happened to her.
    • Played for Drama with Lawrence and Condola.
  • Acid Reflux Nightmare: "Obsessed-Like" has Issa wake up from a bunch of these about her teeth rotting out of her mouth...after consistently eating Raisinets before bed.
  • Almost Kiss: Issa and Nathan, after a day of walking, talking, and enjoying each other's company, go back to her place and have dinner. As they're about to kiss, Issa's tenant's son comes knocking on the door on his mother's behalf, effectively killing the moment...and loudly acknowledging that what he's doing.
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  • Annoying Younger Sibling: Though it isn't clear who's the elder between the two, Ahmal has many shades of this toward Issa. He takes any and every opportunity to get on her nerves.
  • Armor-Piercing Question: When Issa returns to the apartment and Lawrence confronts her about her cheating on him with Daniel.
    Lawrence: Did you fuck him?
  • Ascended Extras: Happens to a few characters:
    • Kelli and Tiffany, Issa's other friends, become main characters after being recurring characters in season 1.
    • Daniel becomes a main character in seasons 2 and 3 after being a recurring character in season 1.
    • Andrew becomes a main character in season 4 after being a recurring character in season 3.
    • Nathan becomes a main character in season 4 after being a recurring character in season 3.
  • Babies Ever After: Kelli reveals that she’s pregnant in the last episode of the show.
  • Bitch in Sheep's Clothing: Issa's boss, Joanne. When Issa did the follow-up calls for the schools with We Got Y'all and asked why they ended their partnerships, she brought this information to Joanne...who basically dressed her down and told her she's the source of the recent problems.
  • Big Fun: Kelli, the group's fat friend. However, it's deconstructed in that her hard partying, devil-may-care attitude makes it hard for people to talk to her about serious things and gets her and ther rest of her friends in trouble, too.
  • Black and Nerdy: Issa qualifies as this, as does Lawrence.
  • Boastful Rap: Issa makes rhymes as a hobby — not because she wants to become a rapper, but as a confidence-boosting exercise. She performs some in front of a crowd in the pilot episode, per her crush's suggestion.
  • Book Ends:
    • Season 4 ended the same way it began - playing a song by Tyler, the Creator, with different conversations happening each time; in the first episode, Issa declares that she doesn't fuck with Molly anymore but, in the season finale, she and Molly are in their favorite restaurant, talking to each other.
    • Even deeper than that, the last scene in Season 4 (the season with the longest gap between seasons) took place in the Merkato Ethiopian restaurant, the same restaurant where Issa and Molly were discussing relationships in the pilot episode. But instead of talking about relationships with other people, they're having a conversation about the relationship they have with one another.
    • The series itself ends with Issa and Molly talking about their relationships to the instrumental to Kelis's "I'm Bossy", the song that Issa rapped "Broken Pussy" over.
  • Both Sides Have a Point:
    • This happens twice in the episode "Real As Fuck." When Issa rightly confronts Daniel for showing up at her fundraiser event uninvited, he calls Issa out on how she wasn't a victim when it came to her cheating on Lawrence with him. The second time was with Issa and Molly. Issa was right to suggest therapy to Molly, due to the latter always having issues with relationships. Molly also calls Issa out on how she acts like the victim when it comes to her lifestyle. She also calls Issa out on how wrong she was to cheat on Lawrence and how Issa didn't deserve him.
    • Happens again between Lawrence and Condola after Elijah is born. Lawrence wants Condola to grant him some grace in regards to parenting Elijah because that's his son as well...but Condola takes time to warm up to him being around because, for all intents and purposes, he wasn't during her pregnancy, and they weren't exactly in a committed relationship when they conceived.
  • Bratty Half-Pint:
    • The kids in the school that Issa worked at, with Dayniece being the ringleader.
    • Trina's son, Benjamin.
  • Cassandra Truth: Lawrence asked Issa twice about the amount of times that the latter and Daniel had sex. He also asks Issa why she invited Daniel to her fundraiser (when really, Daniel just showed up uninvited). When Issa denies both of these allegations, Lawrence accuses her of lying. Downplayed, in that Lawrence was too angry at receiving the news to even believe her.
  • Call-Back: A very tune-out-and-you'll-miss-it example of the trope, but two of the musical artists that have made cameo appearances on the show have also had their songs added to the soundtrack.
  • Casting Gag: A major part of Molly's character is that she Really Gets Around (in fact, at one point, Issa asks her, "Can you teach me how to ho?") and uses a lot of profanity. The actress that plays her, Yvonne Orji, is, in fact, a devout Christian, who only does clean comedy, and is saving her virginity for marriage.
  • Character Development:
    • Issa starts making steps toward living more in line with her desires and goals, and tries harder to be more mindful of the people in her life and their needs. Molly's admonishment about her constantly needing a favor and using people clearly struck a chord with her.
    • Molly is, after four seasons of falling into certain patterns, finally taking risks to break away from old habits and grow...and it's worked out very well for her so far.
  • The Comically Serious: TAUREAN. Literally every interaction Molly has with him paints him as an uptight, rigid know-it-all who doesn't know how to relax and not take himself so seriously. And it's hilarious.
  • Continuity Porn: Quite a few of the notable, seemingly one-off jokes and one-liners turn out not to be one-offs, and show themselves in later episodes or even seasons.
  • Cranky Neighbor: Trina and Dante from Issa's new apartment building qualify. They both have a penchant for complaining about nothing...and when they DO have a reason to complain, they become MUCH worse.
  • Cringe Comedy: A lot of Issa's comedic beats come from the fact that she lacks a fully developed understanding of social cues and, thus, tends to insert awkward jokes into conversation as a method to break the tension.
  • Cute Clumsy Girl: Issa is gorgeous as hell. She also has word vomit at times and lacks grace in the physical realm. She's even stated herself that her happy dance looks like someone having a seizure.
  • Didn't Think This Through: Condola believed that because she had a large supporting family and a good job, it would have been easy for her to raise a child by herself. Reality slaps her hard in the face when her child is born and she realizes how difficult it really is to be a single mother. This causes her to resent Lawrence.
  • Earn Your Happy Ending: Molly ends up marrying Taurean after she’s dealt with so many failed relationships prior to Taurean.
  • Experimented in College: Played for Drama. Jared reveals in one episode that he experimented with his male friend (but considers himself straight after not enjoying the experience), which makes Molly uncomfortable. She asks her friends about it, and while Issa tells her that sexuality is a societal construct and she should stay with him, she takes the advice of her other friend, who says that experimenting makes Jared gay, and breaks up with him. She turns out to be VERY wrong when they run into each other later.
  • Fatal Flaw: The main three characters each have one.
    • Issa's awkwardness has her deep in her own head more often than not, and causes to hyperfocus on her own issues, thus showing a lack of sympathy for others, including Molly and Lawrence.
    • Molly's rigidity of character winds up biting her in the ass frequently. From relationship troubles to interpersonal interactions, she has a tendency to want things her way, no matter the cost.
    • Lawrence has an issue with comparison, particularly where he thinks he's supposed to be in life compared to his friends and family. It's part of the reason his relationship with Issa ended up on the rocks, and he's generally very surprised to see that things aren't running as smoothly as he believes they are for others in his life.
  • "Friends" Rent Control: Notably averted. Issa was forced to move away from The Dunes because of a rent increase she couldn't afford, and she's able to afford rent at her new place due to being the property manager AND driving for Lyft.
  • Green-Eyed Monster: It rears its ugly head in Daniel's case. He's very clearly envious of a fellow producer friend, Khalil (whom he mentored), to the point that Daniel ruins an opportunity to work with an artist by trying to upstage Khalil in front of them.
  • Hate Sink: The bratty children that Issa teaches in the beginning of the show.
  • High-Powered Career Woman: Molly is an impeccably well-dressed, career-driven attorney who struggles to get noticed at her law firm, not because she is a woman, but because (she believes) of systemic racism blinding her firm from seeing her worth. She also struggles in her dating life, partially because she applies the same clinical and critical approach she uses for work to her relationships. In later seasons however, she leaves her firm to work at an all-black law firm where her efforts are more readily recognized. She also learns to be less critical in her relationships and begins to date /eventually marry her coworker Taurean, who approaches work and life in a way similar to Molly.
  • Idiosyncratic Episode Naming: Every episode in the first season has the naming structure "___ As Fuck." The second season's episodes are "Hella ___". Season 3 is "____-like". Season 4's episodes are titled "Lowkey ___", and Season 5's episodes are titled "___, Okay?!".
  • I Just Want to Be Special: Molly does a lot of ill-advised things at her new law firm to stand out as a star player because she doesn't want to feel like just another woman at the firm.
  • Imagine Spot: Used as a frequent Running Gag from Issa. She imagines certain scenarios playing out in her mind (in a fashion that would seem more in line with a TV show), only to snap back to the real world, where something else entirely...and a bit more expected...happens.
  • Instant Humiliation: Just Add YouTube!: Issa's "Broken Pussy" rap becomes an embarrassment, as the kids at the school she volunteers at find the video and start repeating the lyrics.
  • Karmic STD: When Lawrence's bus comes back, there's a Sex Montage of him hooking up with various women, however, the montage ends with him being diagnosed with chlamydia.
  • Laser-Guided Karma: Aparna treats Lawrence exactly the way Lawrence treated Tasha the Teller. It’s well deserved since Lawrence intentionally strung Tasha along only for sex knowing that Tasha wanted a relationship.
  • Motor Mouth: Lawrence's friend, Chad, talks like he's trying to fit all of his thoughts into the 280-character limit of a tweet, and has a remarkable tendency to get off track with his thoughts...and still manage to loop it back around to his original point.
  • Never My Fault:
    • Issa. Her brother even brings this up to her, saying that she can never admit when she's wrong. Thankfully, she grows out of this...mostly.
    • Molly has this same problem, especially with Issa. Whenever she and Issa disagree, she always waits for Issa to come to her and apologize, instead of even considering initiating any apologies. This also bleeds into a lot of Molly's other relationships, where she refuses to see her own missteps in the handling of an issue.
    • Condola is revealed to have this trait in season 5. She resents Lawrence after their child is born and acts as though everything is his fault. This is ignoring the fact that she chose Lawrence as a parent for her baby and that Lawrence admitted that he had no intention of being a father when she revealed to Lawrence that she was pregnant. She ignores these red flags and refuses to hold herself accountable for her own actions that led to her being a single mother.
  • Parents as People: One of the major revelations that leads to Molly and Dro having their situationship was her discovery that her dad cheated on her mother years ago. It alters Molly's view of him, her parents' marriage, and relationships as a whole. It took her a whole season and a half to START reconciling with her father.
  • Plot-Mandated Friendship Failure: Issa and Molly in the midway point of Season 4. The two of them had been experiencing communication issues between each other for the entire season, culminating in a huge argument after Issa's block party which almost ended in the two coming to blows. Every interaction between them after that is palpably tense and uncomfortable until the last episode of the season, when they reach out to each other to finally have a conversation about what's been going on between the two of them lately. Downplayed, however, as the trailer for season 5 shows that they're still working on resolving whatever issues linger between them.
  • Put on a Bus: Lawrence in season 3. returns halfway through the season.
  • Race Fetish: Lawrence has a threesome with two non-black girls who are only with him because he's black (when he can't go a second round, they complain that previous black guys they'd scoped out for this exact reason could).
  • Really Gets Around: Kelly. If she's not banging somebody, she's usually plotting to. It's bad enough that she rarely remembers their names. This trope also applies to Molly to a lesser extent, in that she doesn't keep relationships for very long, but the sex is usually top-notch.
  • "The Reason You Suck" Speech:
    • Issa and Molly give each other these in the episode "Real As Fuck." Issa tells Molly that she is the common denominator in all her failed relationships with men, while Molly calls Issa out on how she complains about her job yet doesn’t make any effort to change it (she also talks about how Issa doesn’t deserve Lawrence because she cheated on him with her ex, Daniel).
    • They have another one with each other in the episode "Lowkey Moving On", addressing different flaws between each other. Molly calls Issa out for her tendency to focus on her own problems more than others' and use or rely on other people; in turn, Issa brings to Molly's attention the fact that she refuses to let go of her anger and any slights against her, however small, and her inability to admit (or even notice) that she can be wrong. It doesn't end well.
  • Reboot Snark: The In-Universe '90s sitcom Kev'yn gets awkwardly rebooted for the 2010s, with forced references to Colin Kaepernick's protests and the #MeToo movement.
  • Rejected Apology: This happens in episode 8 of season 1. When Issa attempts to apologize to Lawrence for cheating on him, Lawrence angrily rejects the apology.
  • Remake Cameo: Sujata Day (Cece in Awkward Black Girl) cameos as one of Issa's coworkers and Tristen J. Winger (Darius aka "Baby Voice") cameos as Issa and Lawrence's gang-member neighbor.
  • Running Gag: Thug Yoda. Even after Issa and Lawrence move out of The Dunes, he crops up around town at least once in every other season.
  • Sassy Black Woman: Issa and Molly actually tend to avoid this, Issa especially. This would actually apply more to Kelli.
  • Scenery Porn: One consistent feature of the show is its loving display of southern Los Angeles, Inglewood in particular.
  • Show Within a Show: Season 1 had a prison reality show Conjugal Visits, season 2 had Due North, a Soap Within a Show about slavery, and season 3 has Kev'yn, which seems to be Martin meets Living Single (complete with cameo from Erika Alexander) with a Cousin Oliver character. Season 4's show is Looking for Latoya, a True Crime parody.
  • Single Woman Seeks Good Man: Molly has the best luck finding good guys to date after a couple duds in Season 1. Now if only she could keep them around...
  • Skinny Dipping: Issa and Nathan, during their walking date, jumped into someone's pool, butt-naked...before getting chased out by the owner.
  • Soul-Crushing Desk Job: We Got Y'all becomes one when Issa is taken out of the field. Her coworkers don't like/respect her, her boss likes to blame her for everything, and her only friend at work is now her superior...meaning a touch of micromanagement. Now that she's no longer out actively helping children, she realizes that she has no passion for the job and that it ultimately fulfills her in no sense.
  • Stepford Smiler: Tiffany, mixed with Stepford Snarker. Oh, Tiffany...constantly saying "it's fine" will not make everything fine. It's rare that she lets the facade fall, but when it does...ya just wanna give her a hug.
  • Stereotype Flip: As stated above, Issa defies the stereotype of a put-together Sassy Black Woman who quips constantly and is highly confident. Instead she is awkward, often at a loss of words, and...well...insecure.
  • Suggested by...: Insecure was originally conceived as a Spin-Off of Awkward Black Girl, but it eventually turned into its own thing with new characters.
  • Surrounded by Idiots: How Issa perceives her (predominantly white) coworkers.
  • Surprise Pregnancy: Played for Drama. Lawrence's ex, Condola, comes back into his life in the last episode after disappearing in S 4 E 5, announcing that she's pregnant with his baby. Nobody saw this coming, especially Issa, and the timing couldn't have been worse. It's bad enough that it separates Issa and Lawrence from one another.
  • Throw the Dog a Bone: Molly finally marries the man of her dreams after dealing with so many bad relationships.
  • Toxic Friend Influence: Chad...Chad...CHAD. Every time Lawrence acts on advice given to him by Chad, the situation gets much worse before it gets any closer to better.
  • Twofer Token Minority: Molly at her old firm was made to appear as this, being a Black woman at a majority white firm. It got to the point that her senior partners wanted to put her picture on the company website, more than likely to display the "diversity" at the firm.
  • Went Crazy When They Left: Issa has a small bout of this after being ghosted by Nathan, to the point of badgering Molly into taking her to his house so she could snoop around his room for any sign of him. Even after finding nothing, she was plotting in her head how to get back there and was contemplating his open window.
  • All Women Are Lustful: There isn't a season goes by where Issa or Molly DON'T have sex. And Kelly? Hoo boy, Kelly.

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