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
- Everything We Know About 'Insecure' Season 4 - xoNecole ... ›
- Insecure Season 5 Premiere Episode, Takeaways - xoNecole: Women's Interest, Love, Wellness, Beauty ›
On set inside of a mid-city Los Angeles studio, it’s all eyes on Chlöe. She slightly shifts her body against a dark backdrop amidst camera clicks and whirs, giving a seductive pout here, and piercing eye contact there. Her chocolate locs are adorned with a few jewels that she requested to spice up the look, and on her shoulders rests a jeweled piece that she asked to be turned around to better showcase her neck (“I feel a bit old,” she said of the original direction). Her shapely figure is tucked into a strapless bodysuit with a deep v-neck that complements her décolletage.
Though subtle, her quiet wardrobe directives give the air of a woman who’s been here before, and certainly knows what she’s doing. At 24 years young, she’s a “Bossy” chick in training— one who’s politely unapologetic and learning the power of her own voice.
“I'm hesitant sometimes to truly speak my mind and speak up for myself and what I believe,” she later confessed to me a couple of weeks after the photoshoot. “It's always scary for me, but now I'm realizing that I have to, in order to gain respect as a Black woman— a young Black woman— who's still navigating who she is. And you know, I'm realizing that closed mouths don't get fed. And if I keep my mouth shut just because I'm afraid of what people's opinions of me will be or turn into, then that's not any way to live.”
For Chlöe, the journey into womanhood is about embracing who she is, without succumbing to the perceptions of what others think of her. From the waist up she’s everything you’d imagine. A gorgeous goddess with the kind of sex appeal that some work hard to embrace but fail to exude. But unbeknownst to anyone not on set, her bottom half is covered by a white robe, surprising coming from the girl who boasts “'Cause my booty so big, Lord, have mercy” on her first hit single “Have Mercy.”
But that’s the beauty of Chlöe. There’s more to her than meets the eye. More than what a few sensual photos sprinkled throughout an Instagram feed could ever tell you. Just like the photo-framing illusion of her portrayed from the waist up, what we know about the songstress is just the tip of the iceberg. There’s so much more beneath the surface.
Some hours later Chlöe leans back in a high chair as her locs are transformed from a formal updo to a seemingly Basquiat-inspired one. It’s pure art, and at her request, no wigs are a part of the day’s ensemble. She’s fully embracing her natural hair, a decision that wasn’t always a socially accepted one.
In the suburbs of Atlanta, Georgia, (Mableton, to be exact) Chlöe began to explore the foundation of her self-image. At an early age she and her younger sister, Halle, demonstrated a vocal prowess and knack for being in front of the camera that caught their parents’ attention. Soon after, they were sent on a parade of local talent shows and auditions, and eventually broke into the digital space with song covers on YouTube.
It was during these early years that Chlöe first learned that the entertainment industry could be unforgiving to those who didn’t fit a particular beauty standard. Despite the then three-year-old snagging a role as the younger version of Beyoncé’s character, Lilly, in Fighting Temptations, casting agents requested that her natural locs be exchanged for more Eurocentric tresses. Ironic, considering that growing up Chlöe saw her hair as no different than that of her peers. “I remember specifically in pre-K we had to do self-portraits and I drew myself with a regular straight ponytail, like how I would put my locs in a ponytail,” she says. “I just never saw myself any different.”
Chlöe would also learn the true meaning of a phrase that would later become an affirmation posted on her bedroom mirror: “Don’t Let the World Dim Your Light.” After attempting to wear wigs to fit in, the Bailey sisters instead chose to rock their locs with pride, which undoubtedly cost them casting roles. Yet they would have the last laugh when making headlines as the “Teen Dreadlocked Duo” who landed a million-dollar contract with Parkwood Entertainment, and the coveted opportunity to be groomed under the tutelage of a world-renowned superstar.
Credit: Derek Blanks
While that could be the end of a beautiful fairytale of self-empowerment, the reality is that it’s just the beginning of the story of her evolution. For most girls, the transition into womanhood takes place in the comfort of their own worlds, often limited to the number of people they allow to have access to them. But for Chlöe, it’s happening in front of millions of critiquing eyes just waiting for an opportunity to either uplift or dissect her through unwarranted commentary.
Many in her position wouldn’t be able to take that kind of pressure. But Chlöe is handling it with grace. “I feel like all of us as humans, we have the right to interpret things how we want,” she says. “I put art out into the world and it's up for interpretation. I'm learning that not everyone is going to always like me and that it's okay.”
Chlöe isn’t the first artist to receive criticism for her carnal content, and she certainly won’t be the last. In 2010, Ciara writhed and rode her way to banishment on BET when the then 24-year-old released her video for “Ride.” In 2006, 25-year-old Beyoncé received backlash for “Déjà Vu."
"I put art out into the world and it's up for interpretation. I'm learning that not everyone is going to always like me and that it's okay.”
So much so that over 5,000 fans signed an online petition demanding that her label re-shoot the video because it was “too sexual.” Even 27-year-old Janet didn’t escape critical headlines when she shed her image of innocence for a more risqué appearance with the 1993 release of janet.
It’s almost as if public reproach is a rite of passage for young Black women R&B singers on the road to stardom. Good girls seemingly “go bad” whenever they embrace the depths of their femininity, and fans only like you on top figuratively. But Chlöe has learned not to bow down to other people’s opinions, but to boss up and control the narrative. As the saying goes, well-behaved women seldom make history. If sex appeal is her weapon, she wields it well.
On set, Chlöe exudes the energy of Aphrodite in an apple red, off-shoulder dress with a sexy high split. In between shots, she mouths the lyrics to Yebba’s “Boomerang” as it echoes throughout the space in steady repetition at my recommendation. The hour grows late, yet Chlöe is heating things up as eyes stare in deep mesmerization of the girl on fire.
Credit: Derek Blanks
Through music, she explores the depths of her being, a journey that seems to be, at its foundation, rooted in self-discovery. Whereas their debut album The Kids Are Alright (2018) boasts a young Chloe x Halle empowering their generation to embrace who they are while finding their place in the world, their second album Ungodly Hour (2020) shows the Bailey sisters shedding the veil of innocence for a more unapologetic bravado.
What fans looked forward to seeing is who Chlöe shows herself to be on her debut solo album In Pieces. In an interview with PEOPLE, she confesses that releasing her first project without her sister was “scary.” "It was a moment of self-doubt where I was like, 'Can I do this without my sister?’”
Chlöe has never been shy about sharing her insecurities or her vulnerabilities, all of which are laced throughout the 14-track album. “I want people to have fun when they listen to it and to just realize that they're not alone and it's okay to be vulnerable and raw and open because none of us are perfect; we're all far from it. And I think it's healing when we all admit to that instead of putting up a facade.”
The gift of time has given the self-professed “big lover girl” more encounters with romance and heartbreak. Love songs once sung for their beautiful riffs and melodies become more than just abstract lyrics and are replaced by real-life experiences, which she tells me is definitely in the music.
In her single “Pray It Away,” for example, she contemplates going to God for healing instead of going at her ex-lover for revenge for his infidelities. “With anything dealing with art, I am completely vulnerable,” she says. “I'm completely myself, I'm completely open and transparent. So it's pretty much all of me and who I am right now.”
Has Chlöe been in love? That still remains to be said. Of course, she’s been linked to a few potential baes, but dating in the digital age isn’t as easy as a double tap or drop of a heart-eyes emoji. It requires a level of trust and vulnerability that’s hard to earn, and easy to mishandle. To let her guard down means to potentially set herself up for disappointment. “It’s difficult dating right now, honestly, because you really have to kind of keep your guard up and pay attention to who's really there for you. And you know, I'm such an affectionate person and I love hard.
"So when I meet the one person that I really, really am into, it's hard for me to see any others and I get attached pretty easily. And you know, I don't know, it's…it's a scary thing.”
Credit: Derek Blanks
“With anything dealing with art, I am completely vulnerable. I'm completely myself, I'm completely open and transparent. So it's pretty much all of me and who I am right now.”
While broken hearts yield good music (queue Adele), what’s in Chlöe’s prayer is the desire to be happy. What does that look like? Well, she’s still figuring that out herself. “Honestly, I'm the type of person who I don't truly learn unless I experience it. So it's like I can view and watch my parents and watch the loving relationships that I see in my life and be like, ‘Oh, I want that. I would love to have that.’ But then I also have to experience [love] on my own and see what my flaws or my faults might be or see what my good things about myself are. I feel like it's really all about self-reflection. And even though our base is our family and that's our foundation, we are still our own individuals and we have to find out specifically the things about ourselves that may be different from what we saw from our parents when we were growing up.”
Her ideal beau, she tells me, is someone she can feel safe to be her fun, goofy self with, but who also gives her the space to be the boss chick chasing her dreams. A man who understands that just because the world compliments her doesn’t mean she doesn’t want to hear those words from his lips or feel it in his touch. A bonus if he shows up on set after a long hard day of work with vegan cinnamon rolls. You know, the basic necessities. “I like whoever I'm with to constantly tell me they love me and that I look beautiful because I do the same. I am a very mushy person, and if I see something or you look good, I will never shy away from saying it out loud. And I want whoever I'm with to do the same, be very vocal. Tell me that you love me. Tell me what you love about me because I'm doing the same for you because that's just the person I am.”
Noted.
Until she meets her match she’s married to the game, and for now, that seems to be perfect matrimony.
Credit: Derek Blanks
On stage at the 2021 American Music Awards, Chlöe solidified her position as a force to be reckoned with. It was a full-circle moment. In 2012, bright-eyed and baby-faced Chloe and Halle would walk onto the set of The Ellen Degeneres Show and blow the audience away as they bellowed out their future mentor’s song. Ellen would present the sisters with tickets to attend the AMAs, assuring them that they would be back and had a promising future. Nine years later, Chlöe descends from the sky cloaked in a snow-white cape and matching midriff-baring bodysuit for her debut performance. It’s the first time she’s graced the stage of the very award show that she was once an audience member of.
As she shakes and shimmies and boom kack kacks out her eight counts, it’s clear that she’s in her element. Just like her VMA performance a couple of months prior, and the many more stages she’ll continue to grace, she brings an energy that has earned her comparisons to the beloved Queen Bey herself. An honorable statement, considering few R&B songstresses are getting accolades for their entertainment capabilities. It’s on these very stages, in front of hundreds of astonished eyes and millions more glued to their televisions at home, that she tells me she feels most sexy. Powerful, even.
But off stage, it’s a different story.
It’s more than just the commentary about her image and media-flamed rumors that get to her. Mentally, she’s in competition with herself. The desire to be the best burns at the back of her mind with every performance, every production, and every time she steps into the booth. Before, she could share the weight of this burden with her sister. Being a part of a duo meant she could turn to Halle for quiet confirmation and encouragement without a word being exchanged. But lately stepping on the stage means stepping out on her own. And despite being a breathtaking, five-time Grammy-nominated star, Chlöe doesn’t escape the reality that sometimes we can be our own worst critics.
Over the last year, she’s been coming to terms with who she is on her own while overcoming the fear of failing to become who she’s destined to be. While the world waits to see how Chlöe wins, the real triumph is in every day that she chooses herself and continues to walk in her purpose. “I don't really have anything all figured out, honestly. But what I try to do, a lot of prayer. I talk to God more and I just try to do things that calm my mind down and just breathe.”
To whom much is given, much will be required. She’s been chosen to walk this path for a reason. Once she fully embraces that everything she’s meant to be is already inside of her, she’ll be an unstoppable force. “My grandma, Elizabeth, she just passed away and my middle name is her [first] name. So I feel like I truly have a responsibility to live up to her legacy that she's left on this earth. I hope I can do that.”
There’s no doubt that she will. With a role in The Fighting Temptations at three years old, a million-dollar record deal, a main role on five seasons of Grown-ish, five Grammy nominations, a number one solo record in Urban and Rhythmic Radio, a debut solo album, and starring roles in recently released movies Praise Thisand Swarm (just to name a few), Chlöe’s certainly already made her mark, and she’s just getting started.
No flex.
Credits
Photographer & Creative Director: Derek Blanks
Executive Producer: Necole Kane
Co-Executive Producer: EJ Jamele
Producer: Erica Turnbull
Digitech: Chris Keller
DP: Alex Nikishin
Gaffer: Simeon Mihaylov
Photo Assistant: Chris Paschal
2nd Photo Assistant: Tyler Umprey
Features Editor: Kiah McBride
Special Projects: Tyeal Howell
Hair: Malcolm Marquez
Makeup: Yolonda Frederick
Fashion Styling: Ashley Sean Thomas
For More: Cover Story: Issa Rae Comes Full Circle
