“I ain’t getting no woot woot’s on my phone”
The iconic dig Issa took at her ex Lawrence after their messy breakup.
If there’s one show that’s made us laugh, cry, and have weekly live-tweet “WTF” moments, it’s “Insecure.” Created by and starring the iconic Issa Rae, this HBO gem is a masterclass in capturing the quirks, complexities, and comedy that comes from being black and living in a big city. From wild dating escapades on dating apps and IRL to the chaos of friend groups, “Insecure” is a mid-20s, early-30s survival guide, full of characters who drop the most hard-hitting lessons I believe we have ever seen from a sitcom in the 2010s.
When I first watched Insecure, I was a college freshman. I was ready to break up with my then-boyfriend because all he brought to the table was a rap career, and a bed in his dad’s basement – which was cute and fun in my senior year of high school, but did not fit who I was becoming.
In comes “Insecure,” the show that brought me, my friends, and even my parents together for live discussions.
I revisit the show as a now 25-year-old who has had a 4-year relationship, lived with that person, planned out my life, realized he was awful, and broke up with him—also a rapper who lives with his dad, I did not learn.
My breakup in March was filled with a lot of crying, pasta, wine, and TV. Of course, the TV part included a one-month rewind and binge of “Insecure,” which ultimately led me to realize the missed lessons I wish I had paid more attention to.
So, grab your wine and get ready to dive into the many lessons of “Insecure” you might have missed in the riotously funny world of Issa Dee. I’ll be breaking down the show’s love lessons, relatable moments, and outrageous character dynamics.
Issa Dee: An Awkward Protagonist
When it comes to navigating love and life as a socially awkward babe, Issa Dee is our girl. From dealing with the problems of being Black in workspaces, to the drama and ugliness in relationships, she keeps it real, raw, and uncut (quite literally because HBO does not hold back on sex scenes *whew*). So, what can we learn from our iconic socially awkward queen?
Lesson 1: “Insecure” teaches us that it’s okay to embrace our quirks and imperfections. In fact, it’s a superpower. Out of everyone on the show, Issa knew herself and walked in her truth the most. Was it a journey? Absolutely. However, along the way, she never changed who she was at the core, she just evolved into better versions and expanded on the talents she already had.
Molly Carter: Get Some Boundaries, Baby
Molly is the queen of setting boundaries, and by that, we mean she tries really hard to set boundaries but often ends up in insane boundary-crossing situations. Her trials and tribulations in the dating world are a vivid reminder that finding love doesn’t mean compromising your self-respect.
Lesson 2: Molly’s journey in “Insecure” is a reminder to know your worth and never settle for less. Drama isn’t a prerequisite for love.
We’ve all been there. Trying to make something that clearly doesn’t fit just because we’re craving a connection—Molly’s blunders remind us that it’s totally okay to have some standards, and giving them up isn’t always the way to find happiness.
Lawrence Walker: From Broken Relationships to Silicon Dreams
Lawrence’s transformation from zero to hero will trigger you as a previous builder girlfriend. He spent two years in his and Issa’s five-year relationship being unemployed and trying (barely) to get his business off the ground. As much as we like to pretend finances don’t affect a relationship, it absolutely does. In fact, an article from Forbes cites 38% of married couples citing financial problems as the cause of their separation.
After his breakup, he went immediately to the typical cis-men coping strategy—dating someone else. Thus, he was constantly looking for Issa in other women and never found it, but ultimately realized this years later.
Lesson 3: Lawrence’s wild ride through “Insecure” is like a crash course in self-reinvention. It screams from the rooftops that you can hit the reset button, rediscover yourself, and find love again, even after a heartbreak. It also reminds us that therapy and being alone can help with healing. If Lawrence had stopped being so influenced by his friends and just taken any type of pause on love after his breakup, he may have been able to start his healing journey earlier.
Kelli Prenny: Baddie With Options
Kelli is the unapologetic, fiercely independent friend who reminds us to embrace our unique quirks and passions. Her vibrant personality, adventurous escapades, and unpredictable love life, are a testament to the importance of personal growth and self-expression.
Lesson 4: Kelli encourages us to pursue our passions and be unapologetically ourselves. Before you dive into a relationship, dive into yourself.
“Insecure” hammers home the idea that personal growth and fulfillment are vital before you get tangled up in a romantic relationship. So, pick up those hobbies, chase your dreams, and be just a self-loving baddie like Kelli.
Daniel King: Bored, Let’s Spin The Block
Daniel, Issa’s past love interest, provides us with a reminder that confronting the past is a necessary step in moving forward. Their reconnection highlights the importance of resolving unresolved feelings from previous relationships.
Lesson 5: Daniel teaches us that before you can fully commit to new love, you need to make peace with your past. Ghosts from relationships past don’t make great third wheels.
“Insecure” dishes out some valuable advice on the importance of resolving past issues and finding closure. After all, dragging the past into your present is like trying to have a threesome with your current partner and your ex—it’s just not going to work.
Nathan Campbell: Love, Mental Health, and Redemption
Nathan is a love interest in Issa’s life who possesses his own set of challenges. His presence in the show highlights the complexities of love, mental health, and the possibility of redemption.
Lesson 6: Nathan’s character teaches viewers about the importance of mental health awareness and communication in a relationship. His journey reminds us that addressing personal struggles and seeking help is a vital part of finding love and redemption. We’re reminded that some “betrayals” can be healed with vulnerability, communication, and patience.
Tiffany DuBois: Pretty Girls Need Love and Help Too
Tiffany is a pretty girl at heart (skee-wee to my Sorors). Her character provides insight into the challenges of maintaining a relationship while becoming a parent. Her storyline emphasizes the importance of adapting to change and supporting each other through life’s transitions.
Lesson 7: Tiffany’s character underscores the significance of communication and teamwork in a relationship, especially when facing major life changes like parenthood. Her experiences serve as a lesson in adapting together as a couple. She’s the only character with a partner the entire show; yet we still get to see her show up as a wife, friend, mother, and evolve through it all.
Derek DuBois: The True King of The Show
Derek, Tiffany’s husband, represents a stable, loving marriage that isn’t without its challenges. Their portrayal emphasizes the value of collaboration, understanding, and unwavering commitment in long-term relationships, even in the face of major life changes like parenthood.
Lesson 8: Derek and Tiffany remind us that marriage is a journey filled with highs and lows, and that’s what makes it beautiful.
“Insecure” underscores the importance of supporting each other through life’s transitions, like parenthood. After all, there are more baby bottles than wine bottles when you become a parent, but it’s all part of the adventure.
Condola Hayes: Mommy Issues
Condola, Lawrence’s ex-girlfriend and co-parenting partner, brings a unique set of challenges and opportunity to the table. Her character highlights the complexities of co-parenting and blended families.
Lesson 9: Condola’s presence in “Insecure” is a powerful lesson in effective communication, patience, and empathy when navigating the challenges of raising a child with an ex-partner.
“Insecure” teaches us about the importance of cooperation and a child-centered approach in co-parenting, even in challenging circumstances. Because, let’s be honest, parenting can be a battlefield, but it’s a battlefield where love should always prevail.
Issa’s Friend Group: Destiny’s Mess
Last but certainly not least, Issa’s friend group reminds us of the strength of sisterhood. Their unwavering friendship and support through thick and thin, are a testament to the significance of having a solid support network when navigating life’s challenges.
Lesson 10: “Insecure” emphasizes the importance of building solid friendships and maintaining a support network for emotional well-being and personal growth.
Issa’s friend group hilariously drives home the message that friends are the family we choose, and their loyalty and support are invaluable. You can always count on them to have your back, no matter how many crazy dating stories you bring to the table.
“Insecure” isn’t just a show; it’s a vibrant, funny guide to navigating love and life. From geeking yourself up with a daily freestyle like Issa, to taking that edible before the outing like Kelli, from boundary-setting to self-discovery, the iconic series will serve as a manual for black generations to come. The lessons from “Insecure” are delivered with humor, authenticity, and flair that will keep us laughing for years to come.
The characters are complex, but remind us so much of our cousins, moms, sisters, dads, neighbors, etc. As we get older, we realize the story of Issa Dee allowed us to connect again as a community and culture. So, when you go on your next “Insecure” binge, pay attention to all the free life and love lessons Issa and everyone around her give us. Embrace your quirks, set those boundaries, pursue personal growth, navigate love’s complexities, and when in doubt remember: live, laugh, Rossi.
