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Everything You Missed From The Newly Dropped 'Insecure' Season 5 Trailer

We are glowing and growing.

Culture & Entertainment

The newly dropped trailer for the fifth and final season of Insecure just dropped and we are feeling the glowed up and growed up teas felt all throughout the two-minute preview of what's to come. Since its debut in 2016, we have laughed, we have cried, we went back and forth about being Team Lawrence, we've gotten annoyed AF by the Molly in our lives, but most of all, we have collectively felt seen in a visual representation of what it means to be a Black woman navigating through life and its many uncertainties. Season 5 of Insecure, which is set to premiere October 24 on HBO Max, is sure to be the homegoing we didn't know we needed.


But in the meantime in between time, let's get caught up on everything you missed in the trailer of what's to come this season on Insecure.

Are Molly and Andrew still together?

HBO/YouTube

At the end of season four, we were left on a cliffhanger of how the conversation between Molly (Yvonne Orji) and Andrew ended. Though their witty banter was cute, that got old real quick as the two had to make adjustments in their lives to balance love and work, but also to manage relationship pains that naturally came about as you are embarking on a new relationship with someone. While Andrew seemed willing to move, Molly seemed a bit stuck in her ways, a reality that also seemed to show its hand in her rocky friendship with Issa (more on that in a few).

From the looks of the trailer, Molly and Asian Bae are no longer a thing.

Molly is putting herself first.

HBO/YouTube

You know what they say, when a woman cuts her hair, she changes her life. From what we saw in the trailer, Molly the character is borrowing some real-life self-love juice from the actress that plays her, Yvonne Orji. Yvonne did a big chop and rocks her natural hair quite often off the screen. Molly ditching the wigs and weaves (some of the time) to embrace her natural hair in the series as well, which we love to see!

She also mentioned to her mother that she is not looking to date, she is focusing on her damn self. Since the start of the series, Molly has always placed a huge emphasis on "having it all" and that included having a time clock on having a man. To see her take a step back to prioritize herself is a huge step. Yasss sis!

Issa and Molly are working on their friendship.

HBO/YouTube

Something that fans loved and were divided on was the friendship breakup Issa Dee and Molly were going through in much of season four's overarching storyline. But, it was really real. As the two friends' lives grew and their priorities shifted, it was like they forgot to have important conversations and then their friendship suffered as a result. In the trailer, Molly can be seen asking Kelli (Natasha Rothwell) how she and Tiffany navigated a similar season in their lives. It's a testament to the fact that sometimes friends can outgrow each other, yes, but if there is effort, it might be possible to grow together.

Tiffany seems back to normal again.

HBO/YouTube

After a bout of baby blues that was explored during an episode last season, Tiffany (Amanda Seales) seems to have bounced back to being her bad and bougie self. Based off her quips in the trailer at least. Last season, she was notably detached from her little one after giving birth, so much so Kelli had to step in and fill in in areas Tiffany couldn't be a part of due to her postpartum depression. She also seems to be settling into her role as a mother.

Kofi Siriboe is in the building.

HBO/YouTube

Kofi Siriboe has been pulling double-duty starring in Queen Sugarand hit Netflix movies like Really Love. This year, he starred in Doja Cat's "Streets" music video and has been making movies as a business owner with his brand, We're Not Kids Anymore. And now sir is about to be guest-starring in the final season of Insecure? Issa Rae, you are a visionary!

Issa is still insecure about her place in the world.

HBO/YouTube

Despite the professional glow-up of Issa's character walking away from the comfort zone of her job (We Got Y'all) to pursue the dream that set her soul on fire, sis is still battling life's many uncertainties. She leveled up by pulling off an incredible event last season and from the looks of it, that move has opened career doors. But as Issa said in the trailer, she's ready for her life to be in the place where she isn't so unsure about everything. Girl, aren't we all?

Some of the career doors that are opening for her are making her feel like she's playing a role versus walking a path where she's successful in reality. It's something that a lot of us are sure to find relatable, myself included, but what's beautiful is amid the self-doubt, there are pockets of joy as she acknowledges where she's come even if she still has a way to go.

What's up with Issa and Lawrence?

HBO/YouTube

Umm, we don't know for sure if Lawrence (Jay Ellis) and Issa are still a couple. But with that earth-shattering announcement he revealed in the season four finale, we can't imagine that their second chance at love survived it. But it's quite possible that the two are doing their best to work through it. Personally, we really see it for her and Nate (Kendrick Sampson). Just saying.

Only time and the season premiere will tell us definitively where she and Lawrence stand post-baby gate.

But also, whose baby is that?!?!

HBO/YouTube

Chile, we don't know. But we have our best guesses... Sips tea.

Watch the official trailer for 'Insecure' Season 5 below: 

Featured image by HBO/YouTube

You may not know her by Elisabeth Ovesen – writer and host of the love, sex and relationships advice podcast Asking for a Friend. But you definitely know her other alter ego, Karrine Steffans, the New York Times best-selling author who lit up the literary and entertainment world when she released what she called a “tell some” memoir, Confessions of a Video Vixen.

Her 2005 barn-burning book gave an inside look at the seemingly glamorous world of being a video vixen in the ‘90s and early 2000s, and exposed the industry’s culture of abuse, intimidation, and misogyny years before the Me Too Movement hit the mainstream. Her follow-up books, The Vixen Diaries (2007) and The Vixen Manual: How To Find, Seduce And Keep The Man You Want (2009) all topped the New York Times best-seller list. After a long social media break, she's back. xoNecole caught up with Ovesen about the impact of her groundbreaking book, what life is like for her now, and why she was never “before her time”– everyone else was just late to the revolution.

xoNecole: Tell me about your new podcast Asking for a Friend with Elisabeth Ovesen and how that came about.

Elisabeth Ovesen: I have a friend who is over [at Blavity] and he just asked me if I wanted to do something with him. And that's just kinda how it happened. It wasn't like some big master plan. Somebody over there was like, “Hey, we need content. We want to do this podcast. Can you do it?” And I was like, “Sure.” And that's that. That was around the holidays and so we started working on it.

xoNecole: Your life and work seem incredibly different from when you first broke out on the scene. Can you talk a bit about the change in your career and how your life is now?

EO: Not that different. I mean my life is very different, of course, but my work isn't really that different. My life is different, of course, because I'm 43. My career started when I was in my 20s, so we're looking at almost 20 years since the beginning of my career. So, naturally life has changed a lot since then.

I don’t think my career has changed a whole lot – not as far as my writing is concerned, and my stream of consciousness with my writing, and my concerns and the subject matter hasn’t changed much. I've always written about interpersonal relationships, sexual shame, male ego fragility, respectability politics – things like that. I always put myself in the center of that to make those points, which I think were greatly missed when I first started writing. I think that society has changed quite a bit. People are more aware. People tell me a lot that I have always been “before my time.” I was writing about things before other people were talking about that; I was concerned about things before my generation seemed to be concerned about things. I wasn't “before my time.” I think it just seems that way to people who are late to the revolution, you know what I mean?

I retired from publishing in 2015, which was always the plan to do 10 years and retire. I was retired from my pen name and just from the business in general in 2015, I could focus on my business, my education and other things, my family. I came back to writing in 2020 over at Medium. The same friend that got me into the podcast, actually as the vice president of content over at Medium and was like, “Hey, we need some content.” I guess I’m his go-to content creator.

xoNecole: Can you expound on why you went back to your birth name versus your stage name?

EO: No, it was nothing to expound upon. I mean, writers have pen names. That’s like asking Diddy, why did he go by Sean? I didn't go back. I've always used that. Nobody was paying attention. I've never not been myself. Karrine Steffans wrote a certain kind of book for a certain kind of audience. She was invented for the urban audience, particularly. She was never meant to live more than 10 years. I have other pen names as well. I write under several names. So, the other ones are just nobody's business right now. Different pen names write different things. And Elisabeth isn’t my real name either. So you'll never know who I really am and you’ll never know what my real name is, because part of being a writer is, for me at least, keeping some sort of anonymity. Anything I do in entertainment is going to amass quite a bit because who I am as a person in my private life isn't the same a lot of times as who I am publicly.

xoNecole: I want to go back to when you published Confessions of a Video Vixen. We are now in this time where people are reevaluating how the media mistreated women in the spotlight in the 2000s, namely women like Britney Spears. So I’d be interested to hear how you feel about that period of your life and how you were treated by the media?

EO: What I said earlier. I think that much of society has evolved quite a bit. When you look back at that time, it was actually shocking how old-fashioned the thinking still was. How women were still treated and how they're still treated now. I mean, it hasn't changed completely. I think that especially for the audience, I think it was shocking for them to see a woman – a woman of color – not be sexually ashamed.

I hate being like other people. I don't want to do what anyone else is doing. I can't conform. I will not conform. I think in 2005 when Confessions was published, that attitude, especially about sex, was very upsetting. Number one, it was upsetting to the men, especially within urban and hip-hop culture, which is built on misogyny and thrives off of it to this day. And the women who protect these men, I think, you know, addressing a demographic that is rooted in trauma that is rooted in sexual shame, trauma, slavery of all kinds, including slavery of the mind – I think it triggered a lot of people to see a Black woman be free in this way.

I think it said a lot about the people who were upset by it. And then there were some in “crossover media,” a lot of white folks were upset too, not gonna lie. But to see it from Black women – Tyra Banks was really upset [when she interviewed me about Confessions in 2005]. Oprah wasn't mad [when she interviewed me]. As long as Oprah wasn’t mad, I was good. I didn't care what anybody else had to say. Oprah was amazing. So, watching Black women defend men, and Black women who had a platform, defend the sexual blackmailing of men: “If you don't do this with me, you won't get this job”; “If you don't do this in my trailer, you're going to have to leave the set”– these are things that I dealt with.

I just happened to be the kind of woman who, because I was a single mother raising my child all by myself and never got any help at all – which I still don't. Like, I'm 24 in college – not a cheap college either – one of the best colleges in the country, and I'm still taking care of him all by myself as a 21-year-old, 20-year-old, young, single mother with no family and no support – I wasn’t about to say no to something that could help me feed my son for a month or two or three.

xoNecole: We are in this post-Me Too climate where women in Hollywood have come forward to talk about the powerful men who have abused them. In the music industry in particular, it seems nearly impossible for any substantive change or movement to take place within music. It's only now after three decades of allegations that R. Kelly has finally been convicted and other men like Russell Simmons continue to roam free despite the multiple allegations against him. Why do you think it's hard for the music industry to face its reckoning?

EO: That's not the music industry, that's urban music. That’s just Black folks who make music and nobody cares about that. That's the thing; nobody cares...Nobody cares. It's not the music industry. It's just an "urban" thing. And when I say "urban," I say that in quotations. Literally, it’s a Black thing, where nobody gives a shit what Black people do to Black people. And Russell didn't go on unchecked, he just had enough money to keep it quiet. But you know, anytime you're dealing with Black women being disrespected, especially by Black men, nobody gives a shit.

And Black people don't police themselves so it doesn't matter. Why should anybody care? And Black women don't care. They'll buy an R. Kelly album right now. They’ll stream that shit right now. They don’t care. So, nobody cares. Nobody cares. And if you're not going to police yourself, then nobody's ever going to care.

xoNecole: Do you have any regrets about anything you wrote or perhaps something you may have omitted?

EO: Absolutely not. No. There's nothing that I wish I would've gone back and said to myself, no. I don’t think at 20-something years old, I'm supposed to understand every little thing. I don't think the 20-something-year-old woman is supposed to understand the world and know exactly what she's doing. I think that one of my biggest regrets, which isn't my regret, but a regret, is that I didn't have better parents. Because a 20-something only knows what she knows based on what she’s seen and what she’s been taught and what she’s told. I had shitty parents and a horrible family. Just terrible. These people had no business having children. None of them. And a lot of our families are like that. And we may pass down those familial curses.

*This interview has been edited and condensed

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Feature image courtesy of Elisabeth Ovesen

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