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Crafted by the ingenious minds of Issa Rae and Larry Wilmore, Insecure grew out to be not just an entertaining dramedy focused on young Black women in LA, but also a gold mine of relatability, poignant observations, and iconic memorable lines. Some of these audacious quotes resonated deeply with its global viewers. That is because they tackle the essence of modern struggles with love, friendship, stereotypes, and identity.
With 139 award nominations and 40 wins, Insecure proved to be an insightful mirror into modern relationships, social issues, and Black women’s lives. From the beginning of the series to Insecure’s ending, the show has become a cultural phenomenon for representing the real voices of Black women dealing with different aspects of contemporary life. The below quotes touch on womanhood, social and cultural nuances, and real-life lessons.
20 “Black Women Aren’t Bitter. They’re Just Tired Of Being Expected To Settle For Less.” – Issa
Issa Dee tried to promote her afterschool program “We Got Y’all” to middle schoolers, only to be met with skepticism about her “white” way of speaking. She ends up confronting them with the stereotype of Black women being “angry” or “bitter.” Issa gives this powerful quote to challenge societal prejudices. However, Issa can’t escape her awkwardness, and a student snarkily yells that her “outfit settled for less.”
19 “Okay, Listen, I Promise Jesus Isn’t Conspiring Against You And Your P*ssy.” – Issa
Issa contemplated the complexities of her 29th birthday in the first episode of Insecure: a stagnant relationship with her jobless boyfriend Lawrence and the seduction of her ex, Daniel. With all of this happening, she was not feeling down but rather contemplating her life and her choices. In one of the raw conversations between Issa and her best friend Molly, they discussed everything from career frustrations to romantic setbacks. Issa then reassures Molly, “Jesus isn’t conspiring against you,” using the familiar irreverent humor that continues and excels throughout the rest of one of the best HBO shows.
18 “I Know What That Sh*t Means. But Being Aggressively Passive Is What I Do Best.” – Issa
Issa’s journey confronting life’s challenges sometimes involves being “aggressively passive” as a coping mechanism that allows her to navigate complex emotional situations with a blend of indirectness and directness at the same time. Along with her awkward raps, her best friend Molly, who is a high-powered attorney, has her own complexities when it comes to relationships as well. Their friendship stands in contrast to how people use various strategies to face the multifaceted issues of modern life.
17 “It Would Just Be Great To Show The Kids That There’s Beauty In Their Own Backyard.” – Issa
One of the main messages of Insecure was the importance of local culture and community and how inspiration doesn’t always have to come from far-off places. Issa surprises Lawrence with breakfast, feeling guilty over cheating with Daniel, and suggests they have a date night. At work, she is distracted by texts from Daniel, so she suggested that “We Got Y’all” hold their next fundraising event somewhere near Inglewood to show the kids “there’s beauty in their own backyard.”
Related: The 10 Best Issa Rae Movies & TV Shows, Ranked According To IMDb
16 “You Gotta F*ck a Lot of Frogs to Get a Good Frog.” – Molly
Molly’s quippy line highlights the ups and downs of modern dating and the importance of going through many possible letdowns to find someone truly special. Issa was not happy that Lawrence forgot her birthday and went to Molly’s house. They had a self-care day to escape their troubles. Molly talks about her experiences with dating through an elite dating app and how women have to go through lots of disappointing encounters before finding someone who is willing to commit.
15 “I’m Molly, And I’m On Molly, So That Means I’m Molly-squared!” – Molly
In one of the most memorable episodes of Insecure, Issa and her friends go on a trip to Coachella, and lots of unexpected events occur. Their trip was supposed to shift away from the tension of their everyday challenges, and amidst this trip, Molly’s lighter side shines through when she gets high on Molly, showcasing her ability to embrace pure enjoyment. It was a refreshing representation of Molly away from her stresses about her job or her relationships, and it captured the essence of friendship and fleeting joy.
14 “Oh, So Now Y’all Wanna Be Woke When A Bitch Been An Alarm Clock Since Day One? Well, Beep Beep, M*th&rf*ck&rs!” – Issa
Issa was getting fed up with the superficial approach to social awareness often displayed by her colleagues at “We Got Y’all,” as it feels like more slogans than real, consistent actions. The staff’s one-dimensional and sometimes plain ignorant suggestions showcase their limited perspective, turning them into a running joke on Insecure. While Issa stayed feeling undervalued as a token Black employee, she started pursuing other gigs as a property manager. Insecure invites viewers to reflect on the complexities of social consciousness and the difference between taking a stance one day and taking the same stance every day.
13 “I’m With Molly On With This One. We Have To Do Better! We Can’t Just Leave It All Up To Chadwick Boseman.” –Tiffany
It’s hard to watch that scene without feeling sad about the late Chadwick Boseman’s death. In an honest discussion among Issa, Molly, Tiffany, and Kelly on the challenges faced by a Black businessperson, Molly expresses disappointment that her new firm lacks the same amenities as her former, predominantly white firm. Tiffany’s pointed remark served as both a tribute and a wake-up call. During this episode’s airing, it was the time when Black Panther was a global cultural phenomenon, and Insecure deliberately chose to recognize Boseman for his contributions to the Black community beyond the Marvel Cinematic Universe.
12 “Beyoncé Is A Better Mother Than Me!” –Tiffany
In the Golden Coachella episode of Insecure, pregnant Tiffany got high on a small piece of the weed brownie. She probably felt left out while her friends were enjoying their single lives. This quote is not just for comedy but a pointed commentary on societal expectations for mothers. Amid the dynamic scene, full of chaos and laughter, Tiffany crying and saying that Beyoncé is a better mother than her for portraying the perfect superhero mother resonates with lots of women who feel the constant pressure to conform to an idealized image of womanhood and motherhood.
11 “Every Black Girl That Went To College Likes Drake.” –Daniel
Insecure’s bad boy Daniel echoed some shared cultural experiences, particularly the sense of community around popular artists like Drake. Issa visited Daniel, and he invited her to drink from a bottle of Moscato. He then said that he thinks this is something that Drake would do. Daniel makes it clear, however, that his intentions are purely physical, leading Issa to a moment of realization that maybe this relationship isn’t good for her.
10 “Thug Yoda Spelled An Entire Sentence Today.” –Lawrence
“Thug Yoda” is the humorous name that Lawrence gives to Issa’s neighbor. A gang member who refuses to utter the letter C for gang rivalry offers constant comedic scenes. Thug Yoda also stands out in a touching scene where he corrects his daughter’s innocent use of the word “Care Bears” to “Bare Bears,” sticking to using gang lingo even in a sentimental moment with his daughter. Lawrence’s joke when he tells Issa over the phone that he spelled a whole sentence is pure comedy, especially when she replies, “That’s Brazy.”
9 “Chrissy Teigen Has A Dope Ass Cookbook.” —Molly
Molly mentioned her admiration for Chrissy Teigen’s cookbook in one of the first episodes of Insecure, reminding viewers that there’s always space for simple joys and hobbies. Issa responded with a cheeky response: “Are you in the kitchen? Please get the f*ck out,” encouraging her to go out and enjoy her single life. Even as Insecure’s characters deal with complex plot lines around relationships, careers, and identity, they still find time for self-care and lighter hobbies.
8 “Maybe It’s Dry As Hell, Maybe It Really Smells. Broken P*ssy. Maybe It’s Really Rough, Maybe It’s Had Enough. Broken P*ssy.” –Issa
In one of the most iconic rap lyrics in Insecure, Issa goes impromptu on an open mic night and raps about Molly’s “broken p*ssy.” Building on a brutally honest conversation with Molly about her relationship struggles, Issa freestyles, “Maybe it’s dry as hell; maybe it really smells… broken p*ssy.” Issa did not know that she was being filmed, and her freestyle rap ended up putting her in trouble at school when her students found out about her rendition on YouTube, which proved to be challenging as it was incredibly hard to control her students after that.
7 “Just Because We Have Standards Does Not Make Us Difficult.” –Molly
Womanhood in Insecure was a strong theme throughout the series, as female friends displayed unconditional support and love for each other without being preachy or condescending. Issa’s friends consistently affirmed their worth and were deserving of happiness from each other. This moment felt like an affirmation not only to Issa but to Molly herself as well. It is a call for confident women to be firm about their own standards and not settle for less.
6 “I Make The Rules. Get In My Line-up.” –Issa
In Insecure’s season 2, Issa introduces the “ho-tation” concept as she goes through the casual dating scene. She cleverly described this train of men that sometimes single women find themselves going through in a short period of time. Issa’s concept invites women to take ownership and set their own dating rules without apology. Women have the right to seek casual flings occasionally, too.
5 “One Day I Woke Up And My D*ck Meter Was All The Way On E.” –Molly
In one of the most hilarious exchanges between Molly and Issa in Insecure, she expressed the emotional fatigue that often happens in modern dating with her “D*ck Meter” metaphor. It is a relatable expression of the exhaustion many people feel from dating and entanglement, and that frustration was echoed by Issa, who answered, “Join the club, bitch. Dick on E, bank account on E. Life on E.” Molly’s phrase became so iconic that people printed it and added it to journals and stickers.
4 “I’m Not Pressed, I’m Just Pressed-Adjacent.” –Molly
This quote encapsulates Molly’s life throughout the entirety of Insecure. “Pressed-adjacent” highlights the pressure that Molly feels is put on her most of the time, especially as she navigates her successful law career and very unfortunate relationships. It captures the essence of being concerned without seeming too anxious, which is Molly’s clever way to face whatever life throws at her without losing control. Molly has been an example of continuously working towards having a balanced life, though a lot of times she put more of her time into her career, she was able to get there eventually.
3 “Maybe I Don’t Wanna Be A Happy Person, ‘Cause Happy People Are Just People Who Haven’t Been Hit With Some Real Sh*t Yet.” –Issa
People who have been through real pain or trauma would be able to relate to Issa’s quote. Some people take a long time to get over their cynical view that happiness is a result of naivety or a lack of exposure to life’s harsh realities. Issa changes her pessimistic view as the show progresses, but her quote invites viewers to explore what happiness truly means and whether it can coexist with the real challenges and struggles that most people will inevitably face at least once in their lives.
2 “You Know What That Is? Growth.” –Kelli
Kelli’s declaration of “You know what that is? Growth.” during Insecure’s season 3 party has become one of the most shareable memes on social media. Widely recognized as one of the best characters on HBO’s Insecure, Kelli delivered this line with humor and an incredibly well-delivered hand gesture mimicking a sprouting plant. This scene has since been shared among friends when they want to celebrate moments of personal growth and transformative life stages. Kelli captures the essence of being a constant, supportive friend in Issa’s life.
1 “Happiness Is A Choice.” –Lawrence
Lawrence and Issa had a long journey that brought them back to each other in Insecure‘s ending. Throughout the series, they both navigate an emotional roller coaster of love, betrayal, growth, and reconciliation. They realized that their happiness individually and together cannot be a result of fate or external circumstances, but a conscious choice they have to make. Whether it’s Issa deciding to work on herself or Lawrence contemplating the importance of loyalty and career ambition, this phrase encapsulates the hard decisions they’ve both made. Lawrence told Issa that he was choosing to be happy with her.