In Insecure: Season 1, Issa and Molly are definitely not “killing it” the way most modern-day black women are portrayed. These best friends must deal with their own real-life flaws as they attempt to navigate different worlds and cope with an endless series of uncomfortable everyday experiences. Over the course of the season, Issa attempts to figure out what she wants out of life and how to take control of it, while Molly, a corporate attorney who appears to have everything together, struggles inside as she looks for external ways to fix her life.

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Giveaway Alert: Comment Below or Tweet @melodysimpson using #InsecureHBO what your favorite moment of Insecure Season One was for a chance to win the complete first season on Digital HD! Comment/Tweet by Friday, January 13 11:59pm ET. Winner will be announced within 24 hours and must respond within 48 hours or another winner will be chosen.

Insecure follows 29 year old, Issa Dee as she navigates her way through stereotypes at her job, standing by her boyfriend who struggles to find a job, and what she hypes herself up to be in the mirror when no one’s around vs. what she actually presents herself to be to the world.

On the show, Issa works for a non profit organization for underprivileged youth in urban areas and she is the token black girl on the staff.  I loved the dynamic of her in the workplace. I love how this setting shows viewers all over the world a snippet of what’s like, what’s expected from you as a black woman in the workplace and in (white) society overall. I love the no holds barred approach in showing, through Issa’s co-workers, that stereotyping people and growing up with the mentality that those things are actually true often stays with you…and even when trying to push against the norm that we’ve created, it’s not easy to let go of those misconceptions. The humor in that, both when people recognize it and when they don’t, is displayed masterfully here. If you watched and loved Issa Rae’s Awkward Black Girl, everything you loved about the heart of that show (and not just in the work setting) is brought over, so chances are, if you wanted a certain theme or topic explored more on that show, it has been or will be on this one.

Then there’s the romance. Issa’s been dating Lawrence for five years but for four of which, Lawrence has been “getting his life together” and Issa is, understandably, tired of it. She won’t settle for this. So she battles with what to do now that she’s 1) recognized the conflict and 2) decided to do something about it. When we come into their relationship, Lawrence is in a employment/financial rut. It’s okay to be in a rut about our circumstance, we all get stuck in ruts. But his overstays its welcome.

Watching Issa’s response…oh man, it’s such a wild roller coaster we go on in the first season. Especially considering Lawrence does find a job, and then an even better one but he questions whether to take the better one when he realizes the best one is what he can create on his own. And once again, without spoiling anything, Issa and Lawrence are on different pages. More often than not for these two, different pages.

Between Issa’s relationship drama and her best friend, Molly’s lack of a serious relationship for there to be drama, we explore what it’s like to misread signals, what it’s like to drive through mixed signals, and what it’s like looking for love, fighting for love, leaning on the rest. Through dating and the romantic relationship discussion on the show, we dive into the reality of 1) being a successful single black woman trying not to be intimidating to black men or settle for any man 2) sexuality in Black culture and the double standard with Black men who are gay/bisexual and 2) what’s accepted of you and what’s rejected from you in the dating pool by your own society of people. There’s so much to cover and I love, love, love the pacing of the show and how everything is being executed at this point.

From lovers to friends… my most cherished relationship dynamic on the show is that of best friends Issa and Molly. Siblings aside, no one can show you yourself like a best friend can. For better or for worse, we see it all. I LOVE the complexities of friendship, of best friendship brought to the screen. Seeing the tug of war between Issa and Molly when one is lying to themselves and the other is trying to knock some sense into them. When one needs the other to life them up personally, in their career, or otherwise. We see the good and the ugly and you guys, it’s so dynamic and so wonderful. It’s perhaps my favorite friendship of the 2015-2016 TV season. (Okay, it ties with a certain friendship on NBC’s The Good Place but that’s another discussion. Anyway…)

Through career choices, through lovers, through friends, through Issa’s life and those closest to her, we get to follow a group of people underestimating us, deceiving themselves, disappointing themselves…being insecure. It’s a breath of fresh air because that’s life. At least, as a black girl myself, living a life mirrored on this show, that’s mine. It’s nice to know I’m not alone in what Issa calls the prequel to #BlackGirlMagic.

If I had to sum up a moment in Insecure that is literally me, my everyday awkward black girl experience, it would have to be this:

This is a story about the waves of confidence and fear that we coast to get to where we want to be as we ride instead to where we really need to be. It’s about how society guides us along the way and how well we as individuals allow that guidance. It’s about what we do when strangers and people who think they know you and people who you think should know you, comment on your style and attitude and objectives and motives without thinking, with zero clue of what they’re talking about, with zero context. Add on top of that cultural markers and oh my God. Talk about endless material. There are countless moments in season one that I relate to, that other awkward black girls relate to. Based on season one alone, this is easily one of the most relatable shows that I’ve ever watched and I can’t even begin to express how thankful I am for that. Especially knowing that this show was created by, written by and is starring a young Black woman and the writer’s room is easily the most diverse writer’s room in the game right now.

Long story short, season one of Insecure gives me life. The awkward black girl experience is portrayed so genuinely and hilariously. It’s smart. It’s sexy. It’s heartwarming. It’s heartbreaking. What an explosive season finale! I cannot believe all of the goodness we got in just one season, in just eight episodes. And Episode 1.06 “Guilty As F**k” is directed by the legendary, Debbie Allen. Basically, Insecure is a true gem and you want this TV show in your collection.

Finally, on a side note, as someone who co-hosted and edited Gleek Squad Podcast almost a decade ago (hey, fellow Gleeks!), I got a real kick out of a certain moment. Which brings me to…my favorite quote of the entire first season? This exchange:

“Do you listen to yourself?” – Issa
“All the time. I have a podcast.” – Kelli

What were some of your favorite quotes from season one?

Special Features

On the Insecure Set with Issa Rae (4:35 minutes) – In this feature, we follow Issa Rae from 9am to 11pm on the set of Insecure, across various locations in Los Angeles. From the hair & makeup trailer to behind the scenes on set, this is an exciting look into the making of the show. At one point in the day, the crew stops traffic on Crenshaw Blvd. Talk about being a big deal. What’s really exciting about this feature is that throughout this long day, Issa Rae’s passion for what she’s doing never wavers. It’s beautiful to see which makes this a definite must watch.

Appearing in this Feature:
Hairstylist, Felicia Leatherwood
Showrunner, Prentice Penny
Director, Melina Matsoukas
Cast Members, Y’lan Noel, Tristen J. Winge, Neil Brown Jr., Jay Ellis

Insecure: In the Room (2:02 minutes) – In so little time, so much is covered here as the creatives reflect on their time in the writers room for the first season of the show and seeing what they envisioned come to life, the importance of bringing the diversity in the room to the screen, and the goal to follow home the black girl after she’s been pigeonholed all day by the majority. It’s a fun, quick reflection and recap of the heart of the show that you should definitely check out.

Appearing in this Feature:
Showrunner, Prentice Penny
Co-Executive Producer, Dayna Lynne North

Conjugal Visits (4:04 minutes) – In case you’re in the mood for an actual edit of the TV show that Issa and Lawrence watch on their down time, here it is in all its ridiculous glory.

Insecure: Season 1 is available now on Digital HD. Stay tuned for Season 2 of Insecure coming soon to HBO.