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Five Takeaways From The First Episode Of The Last Season Of 'Insecure'

Spoiler alert: this is gonna be an emotional ride.

Culture & Entertainment

Sunday night was filled with watch parties, buzzing group chats, and never-ending social media posts all in celebration of the beginning of the end to HBO's Insecure. From debates surrounding friendship and relationships to healthy discussions around therapy, postpartum, and office culture, Insecure explored it all, and in a way that felt authentic and incredibly familiar. And while I'm a lover of many different types of television shows, I can honestly say Insecure is just different, special.


And I think I speak for a lot of us when I say as excited as I was for it to come back, I'm just as sad for its approaching end. But, if the first episode of season five is any indication of what's to come, they're definitely going out with a bang. And by that, I mean an emotional bang. Because this first episode was a lot to digest. By the way, I'm about to drop a lot of spoilers so if you haven't watched, head to HBO Max and then come back. But, for those of you that are caught up, here are some of our takeaways from the season five premiere episode.

1.Looking back helps you move forward.

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There was something so uniquely beautiful about the cast going back to Stanford (Issa Rae's actual alma mater) for their 10-year reunion. It showed them in a way we kind of always imagined, walking through campus, talking, laughing, and making the memories that formed the relationships we've seen throughout the show. I also have to believe it served as a really good reminder of the things the characters may have previously wanted out of life and how some of those things may have changed while others stayed the same.

For example in this episode, Issa Dee commented on how since Tiffany and Derrick's first date, everyone knew they were a match. And now, here the married couple was walking together happily on the same campus. On the other hand, there's Issa who, while in school, thought she'd become a lawyer and open a firm with Molly, yet there she was excitedly waiting to speak on a panel about being an entrepreneur.

Sometimes looking back allows you to remember the things you wanted, celebrate the things you have, and re-evaluate what's next.

2.It's OK to take meaningful risks.

Pretty early in the episode, we learn that Issa has been flewed out, thanks to her alma mater, and is on a special panel to talk about her new company, BLOCC (Black Life Opportunity, Culture, and Connection). However, when she stutters over what the acronym stands for, it becomes apparent that she's still ironing out the kinks. Nevertheless, during the panel, she's asked many intimidating questions like, "What's the biggest lesson you learned on your journey?" and "When did you know you were on the right path?" And for a moment, we see Issa appear uncomfortable after making one of those awkward yet hilarious outbursts we've grown accustomed to hearing.

But, then she does something else, she shares a transparent truth, that's she's not sure that she's made the right decision and wonders if she's wasting her time. And while that response may not have been a hit with the panel audience, it resonates with Insecure's. Because, thanks to layoffs and toxic office cultures coupled with social media's need to appear like we have it all together, many Insecure viewers know all too well about having to change career paths. And there's something so freeing in embracing uncertainty and chasing true fulfillment.

3.Some bonds are forever.

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As we know, Insecure always starts a lot of conversation. I mean, one of the best things about the episodes is the gender wars and Twitter threads that appear after they air. But, one pretty clear thing is that this show is full of passionate relationships. And I don't just mean romantically. Issa and Molly's friendship has been a highlight of the show, and when season five begins, we're not quite positive where they stand. I mean sure, they seem friendly, but they're supposed to be best friends.

Friendly isn't really a word I'd use to describe the chemistry between best friends, it's supposed to be much deeper and more comfortable, but the two are clearly putting forth an effort to fix it. However, when they're at gunpoint holding onto each other (thanks to that shady Cheyenne) and later belting out in laughter, it becomes apparent that they have a forever connection. That's how it is with some people. You can go a long time without talking or even suffer hurdles in the relationship, but you're still always going to care for them, and I think Issa and Molly are a really good example of that.

4.Friends can be your soulmates, too.

One of the things I really liked about this episode is that we learned even more about Kelli. Because while she's one of my favorite characters, I don't know as much about her as I do the others. And when the girls are in the car before all hell breaks loose, Kelli irritably shares an authentic truth: she feels like everyone only sees her as the "funny friend." And while the rest of the characters laugh, Tiffany looks at her sympathetically.

To me, that moment spoke to their relationship. Because sometimes when it seems that everyone else doesn't understand you, the person who truly gets you, always will. And at the end of the show when Tiffany verbalizes that emotion to the group by saying "she's my soulmate, sorry Derrick," as she apologizes to her husband, it was just a beautiful reminder of the people in my life I'm thankful for. And that sometimes, friends can be soulmates too.

5.Trust your gut.

Whew, this one was hard to type. Because I'm one of the people that is rooting for Issa and Lawrence to find their way back to each other. Now, I know it's been quite messy and he has a whole side baby now, but they clearly love each other! Still, if there's one thing this life has taught me, it's to trust your gut, intuition, or vibe – whatever you want to call it –it's there for a reason. And when Issa was riding in the car with Lawrence during that final scene, it was obvious there was something major she needed to get off her chest. And whether the decision to end things is temporary or permanent, it's good to know she trusted herself.

Who knows what would've happened if she stayed when she truly wanted to leave? Maybe she would have cheated on him again, maybe she would have ruined their relationship altogether, or even formed a wedge between him and his child. Now, I know that may have gone too far, but my point is it reminded me to always trust myself, even if it's difficult or uncomfortable to do so. Because you never know what the repercussions may be. Still, I hope they find their way back to each other.

But maybe she can grab dinner with Daniel before that because I'd like to see him on-screen one more time. (smiles)

Featured image by Giphy

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