HBO's award-winning dramedy Insecure stars comedian Issa Rae as a fictionalized version of herself. Issa is a Los Angeles-based Black woman trying to make sense of life while navigating the trials and tribulations of her late twenties. With her clique of friends, lovers, and exes, Issa dives head-first into contemporary life.
Ultimately, romance plays a big role in the series. Whether it's Kelly's sexual exploits which she loves to describe in great detail — or Molly's struggle to balance love and a career, there's plenty of salacious activity to be found. This list showcases 10 of the most hilarious quotes about dating featured in Insecure.
"Of Course I Want My Man Back."
The first few seasons of Insecure focus on the relationship between Issa and Lawrence. The couple finds themselves in a rut after being together for five years, and the relationship implodes after Issa cheats on Lawrence with her ex, Daniel.
While Issa pretends to be okay with the break-up, she's really hurting inside. When she has a chance to try to make it work, she jumps at it. Ultimately, Issa and Lawrence part ways, both going on personal journeys of self-discovery.
"You Gotta Kiss A Lot Of Frogs To Get A Good Frog."
Issa's BFF Molly, an accomplished lawyer, shares this piece of advice with Issa in the wake of her breakup with Lawrence. While Molly uses more explicit language in the series, the bulk of the message remains in the quote above.
Issa goes on to "kiss many frogs" as the series progresses. She's at her best, though, when she focuses on herself.
"Girl, What Is So Crazy About Buying Fake Desserts To Bring To Andrew So I Can See If Nathan's Home?"
Season 3 features a new man in Issa's life in the sultry Nathan. After they finally make the moves on each other, Nathan ghosts Issa. Desperate to figure out why, Issa concocts a plan to show up at Nathan's house with Molly.
Issa and Molly bring desserts to Andrew, Nathan's roommate, in order to see if Nathan's home. It turns out he isn't, but Issa doesn't mind scouring his room for evidence of his whereabouts.
"I Make The Rules. Get In My Line-Up."
Issa strives toward complete independence in Insecure, and audiences feel she gets in season 4. She's enjoying casual sex, focusing on her career, and engaging with her community by planning a block party.
One of Issa's beaus in the new season is a TSA agent who doesn't disappoint in bed. Issa isn't in it for keeps, though, and she eventually moves on.
"We. Are. Not. Dating."
Issa and Molly rely on each other for a lot of emotional and mental support. While Issa works to get her act together and figure out who she is, she turns to Molly on the reg for help.
Molly keeps the boundaries clear, though, and she reminds Issa she's not her man. While Molly shows up as BFF, she doesn't want to play the role of a romantic partner for her girl.
"Why Can't Black Men Explore Their Sexuality Without Being Labeled As Gay Or Bi Or Whatever?"
Insecure's characters are predominantly straight, but the show tackles gender roles, homophobia, and sexual repression. Issa Rae often fills the series with important commentary about contemporary dating.
The show's male characters both highlight and subvert heteronormative standards. The series manages to open this important door without sacrificing its humor.
"It's My Sexy Walk."
Sex is front and center in Insecure. Instead of gliding around it, the series tackles sex head-on. Not only it is groundbreaking for the comedy to star a Black woman; it's also groundbreaking for Insecure to focus on Black female sexuality without reservation.
The jokes can be as tame as Issa doing her sexy walk in public, but they can also be dirty and graphic, which is what makes Insecure so wonderful and unique.
"Right, Because Everyone Automatically Listens To A Woman When She Opens Her Mouth."
Molly is a career woman who works as a lawyer, and sees through the office dynamics that impact her both as a woman and a Black woman.
Molly spends most of the series grappling with being true to herself and advancing her career. Her relatable storyline is made all the more entertaining by her sarcastic sense of humor.
"Honestly, I Want To Live By Myself."
Issa toggles between wanting independence and a relationship, especially in the wake of her long-term partnership with Lawrence. She'll wax poetic about independence and then bemoan her singlehood in the next breathe.
Issa comes to terms with her heartbreak and her past. She also finally gets her own place and does a great job decorating it.
"Just Because We Have Standards Does Not Make Us Difficult."
In addition to romance, Insecure also explores female camaraderie. Without being overly didactic, the series shows how women band together to support and love each other. These women deserve the absolute best out of love and life, and don't hesitate to remind their friends the same thing.