Adyia Gibson

27 February 2024

Dr. Whitener

English 102-021

Evaluation Essay

Insecure

Insecure is a show created by Issa Rae and was transformed from one of her web series

“The Misadventures of Awkward Black”. Insecure made its debut premiere on HBO Max on

September 26, 2016, and later showed weekly as of October 9, 2016. The show was filled with

adventure, drama, and satisfying comedy which demanded the viewers’ attention weekly. Issa

created this show because of the lack of shows about basic black people with everyday struggles.

This show portrayed real life events while they were going on in real time while they were

filming. Issa Rae used popular music created by many black artists throughout the show to

support artist and their music but also to support different messages in the scenes for each

episode. The show was based in Los Angles, California. Most of the scenes where shot in Issa

Rae’s hometown South L.A. Some of the main characters of the show was Issa Dee, Lawrence

Walker, Molly Carter, Kelli Prenny, and Tiffany DuBois. Issa Rae only wrote this show to last

for five seasons.

The main character of “Insecure” was Issa Dee. She was labeled as awkward during the

show, and she was determined to conquer each situation that occurred from day to day. Within

each challenge she faced she always found a way to face it and move on. During season three

Issa decided to quit her job at “We Got Y’all” which was a nonprofit organization that help kids

after school with their homework. After she quit her job, she started doing a side hustle called
Lyft to make a little money and she had to move out of her apartment because she could no

longer afford the rent anymore. She decided to move in with her best friend Molly for a moment

while trying to find a place to stay. After she left Molly place she lived with her ex-boyfriend

Daniel, for a while until she found a job and a place of her own. Issa found a job working as a

landlord at an apartment complex which allowed her rent to be reduced. One of Issa big dreams

was to throw a block party to help black artists and businesses. This idea took a lot of planning

and money. Once she planned out everything, she held a showcase to present her idea to different

sponsors who would allocate funds to sponsor her block party. Through the challenges that Issa

faced she still managed to be there for anyone that was closed to her.

In June of 2023, finally was able to watch Insecure when it was put on Netflix. After

finishing the series within a few days, the realization of how organized and well thought-out this

show was depicted piqued my interest. And was yearning for more seasons but had to remember

it was a five season show. A few months later I decided to watch the show again for the second

season and gained another opinion about the show. Before watching the show again, I thought

that Molly, who was Issa best friend, was a good friend. She was not a good friend because every

time they would have an argument Molly would blame everything on Issa and never take

accountability for what she did. For example, in season four and episode four Molly tells Issa

how she ran into an old college friend and the friend was telling her about therapy. During

college the friend was wild and had a few issues, but she was telling Molly how therapy helped

her. Molly defined therapy as a place for crazy people. Issa was trying to explain to Molly that

most people get the wrong idea when anyone mentions therapy. After that conversation Molly

was mad at Issa and lashed out at Issa saying maybe you need therapy because every time
something good comes into your life you mess it up. This argument happened after a charity

event for Issa job.

Later, during the other seasons Molly and Issa stopped communicating which lasted for a

few months. Eventually Issa reached out to go get breakfast at their favorite spot. Before Molly

arrives, Issa was very nervous because this situation could either go good or bad due to their past

altercations. Once Molly shows up, they both hug and talk about what has been happening since

they stopped communicating. Everything goes well but, they never talked about the situation that

led them to stop talking to each other. In the next episode Molly invites Issa and her boyfriend

Nathan, over for game night with Molly’s boyfriend Andrew, also. Everything seems to be going

good until Molly was trying to text her boyfriend saying “I’m trying” with her but instead

accidentally sent it to Issa. Once Issa receives the message she walks out and Molly follows her,

once Issa turns around her and Molly has a few words then Molly says “Maybe we just outgrew

each other” Issa agrees. Eventually at the end of series they rekindle their friendship. Issa was

even a bridesmaid at Molly wedding.

Another character that was questionable would-be Lawrence. Lawrence was Issa

boyfriend during the first season. On the first episode of Insecure it was Issa birthday and

Lawrence forgot that it was her birthday, and he recently just lost his job. So, for her birthday he

did not get her anything. All he did was lay on the couch and tell her happy birthday. Issa was

upset but her best friend Molly asked her to hang out. They decided to go to a karaoke club, at

the club Issa ran into her old friend Daniel and she decided to get on the stage and freestyle.

After Issa and Molly left the club, Daniel texted Issa. A few episodes later Laurence finds out

that Issa cheated on him with Daniel. Laurence was mad at Issa, but Issa excuse was that

Lawrence was depressed and he was not acting like her boyfriend, he was not doing sweet things
for her anymore. They decided to end their relationship and Lawrence moved out. By the of the

show Issa and Lawrence decided to work everything out and get back together but there were

still the problems. Once they finally decided to get back together, Lawrence found out that his

ex- girlfriend Condola was pregnant with his child, and she wanted to keep it, but Lawrence did

not. Eventually Lawrence told Issa and her reaction was that she was upset because she thought

that for once everything was going right in her life. They ended up breaking up again and going

their separate ways.

In conclusion, the show commanded my attention and kept me engaged. Insecure taught

many life lessons, especially how to maneuver in life when unexpected situations occur and how

to stay focused and strive for what is important. Issa was able to acknowledge what the issues

were and how to come up with a resolution. Even though some of the characters were

questionable, Issa was able to learn how to deal and handle each character in her own way. I was

not a fan of how that last season ended because everything was rushed into one episode. Each

character was able to have their happy ending and their friendship was stronger than ever. Just as

we must do in life today and keep moving. Once a person shows you their representative, you

should believe them and move accordingly. I feel like Issa did not have a proper ending, but it

shows that you can do everything to get away from a person and still end up with them.
 Works Cited

Giorgis, Hannah. “How Issa Rae Built the World of ‘Insecure.’” The Atlantic, Atlantic Media
Company, 25 Dec. 2021, www.theatlantic.com/culture/archive/2021/12/issa-rae-insecure-
hbo-series-finale/621100/.

Deggans, Eric. “HBO’s ‘insecure’ Soars by Staying True to Its Revolutionary Mission.” NPR,
NPR, 24 Oct. 2021, www.npr.org/2021/10/24/1048271938/hbos-insecure-soars-by-
staying-true-to-its-revolutionary-mission.