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 ›
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While speaking to xoNecole, Eva shares that she’s a lot like the beloved 1994 character in many ways. “Lyric is so me. She's the odd flower. A flower nonetheless, but definitely not a peony,” she tells us.
“She's not the average flower you see presented, and so she reminds me of myself. I'm a sunflower, beautiful, but different. And what I loved about her character then, and even more so now, is that she was very sure of herself.
"Sure of what she wanted in life and okay to sacrifice her moments right now, to get what she knew she deserved later. And that is me. I'm not an instant gratification kind of a person. I am a long game. I'm not a sprinter, I'm a marathon.
America first fell in love with Eva when she graced our screens on cycle 3 of America’s Next Top Model in 2004, which she emerged as the winner. Since then, she's ventured into different avenues, from acting on various TV series like House of Payne to starring on Real Housewives of Atlanta.
Je-Caryous Johnson Entertainment
Eva praises her castmates and the play’s producer, Je’Caryous for her positive experience. “You know what? Je’Caryous fuels my audacity car daily, ‘cause I consider myself an extremely audacious woman, and I believe in what I know, even if no one else knows it, because God gave it to me. So I know what I know. That is who Je’Caryous is.”
But the mom of three isn’t the only one in the family who enjoys acting. Eva reveals her daughter Marley has also caught the acting bug.
“It is the most adorable thing you can ever see. She’s got a part in her school play. She's in her chorus, and she loves it,” she says. “I don't know if she loves it, because it's like, mommy does it, so maybe I should do it, but there is something about her.”
Overall, Eva hopes that her contribution to the role and the play as a whole serves as motivation for others to reach for the stars.
“I want them to walk out with hope. I want them to re-vision their dreams. Whatever they were. Whatever they are. To re-see them and then have that thing inside of them say, ‘You know what? I'm going to do that. Whatever dream you put on the back burner, go pick it up.
"Whatever dream you've accomplished, make a new dream, but continue to reach for the stars. Continue to reach for what is beyond what people say we can do, especially as [a] Black collective but especially as Black women. When it comes to us and who we are and what we accept and what we're worth, it's not about having seen it before. It's about knowing that I deserve it.”
This interview has been edited for length and clarity.
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Feature image by Leon Bennett/WireImage
When I resolved to walk away from my 13-year relationship, admittedly, I wasn’t thinking about dating at all. My ex was a good man. He was kind, he was cool, but I knew he wasn’t my man. God knew that, too, even before I did.
We had reached a fork in the road: I was growing deeper in my faith, wanting to center God in every part of my life, including my purpose. He was walking a different path, and we were no longer aligned. Turns out, you can spend 13 years with someone and still be emotionally malnourished.
As our relationship came to its end, I learned that longevity isn’t proof of alignment. I learned that a man being “good” isn’t enough. A man can be kind but not called to walk beside you in your purpose. That being unclear about your values will always cost you time.
And delaying your desires in the name of comfort? That’ll cost you even more. I knew I never wanted to make that mistake again.
Still, even knowing it was right to let him go, walking away felt like mourning a death. I dated casually after that: flings and situationships here and there. But they took more than they gave. I was left depleted more than fulfilled, so I made a conscious decision to stop dating altogether.
Around the same time, my mother was diagnosed with a brain injury that left her unable to form short-term memories. My sister and I became her caregivers along with my dad. But just as I got her stabilized, my father was diagnosed with blood cancer. At one point, he was bedridden.
So no, I wasn’t thinking about love. I was thinking about survival.
For two years, I didn’t give out my number. Didn’t go on a single date. I was tired, mentally, emotionally, and spiritually. But not just from dating. From everything.
Those two years weren’t about fear, they were about focus. I was caregiving, grieving, and building a startup from the ground up. I had nothing left to give romantically. So when my birthday came around in September 2023, I knew I needed stillness to replenish what I had lost.
I went to Joshua Tree alone, I booked a tiny home in the middle of the desert, and I told myself: “I’m going to be still.” For five days, I read, prayed, fasted, and listened to jazz and classical music. No distractions.
Courtesy of Shirley Vernae
On the drive back to LAX, it hit me like a ton of bricks, and I couldn’t unsee it: I had invested in every other area of my life, except my love life. I realized then that my love life deserved a strategy, too.
So, I did what I always do when I want to grow in an area: I found someone wiser. I found an expert who could guide me in the form of a dating coach, and I hired him. Because love is too sacred to leave to chance. And I was finally ready to build it on purpose.
To some, hiring a dating coach might’ve looked like desperation. But desperation doesn’t look like pausing for two years, it looks like settling for crumbs and calling it a meal. You’ll mistake attention for affection, and chaos for chemistry. Desperation doesn’t discern. It just consumes.
That wasn’t me. Not only was I not desperate, but I was a little too comfortable being single.
I didn’t invest $10K+ in a dating coach because I was desperate. I invested because I was done repeating old patterns. Strategy is getting honest about your desire and then building a pathway toward it with clarity, with guidance, and with God.
I had invested in every other area of my life, my business, my health, and my growth. Why would my love life be the one place I left to chance?
So no, I wasn’t desperate. I was ready. Ready to stop guessing. Ready to stop wasting time. Ready to become the kind of woman who could receive the kind of love I prayed for.
But before I could become her, I had to face the parts of me still holding on to old beliefs.
When I walked away from that relationship and got into therapy, everything shifted. My therapist helped me unpack my wounds, my conditioning, and the patterns I couldn’t see on my own. And when the fog cleared, I was 100% sure: God had given me this desire. And I was not going to let doubt, distraction, or misalignment steal it from me.
This wasn’t just about having a plan, it was about being in divine alignment.
Between 2023 and now, I’ve invested close to $12,000 in coaching. I joined Anwar White’s Get Your Guy program in October 2023. The program was $7,500 over six months—that’s $1,250 a month, less than some people spend on luxury items they’ll outgrow. And for me? It made perfect sense.
After starting the program, I met my now-husband that December. We became official in spring 2024, and he proposed in January 2025.
But the real shift wasn’t him. It was me. I no longer chased anything—not men, not clients, not friendships. I stopped striving and started trusting. I started existing, and I let what was aligned come to me.
And when he came, he came steady. Consistent. Intentional. Reliable. Joyful. He was deeply committed to my happiness before anything else. He doesn’t move unless it’s with care for my heart.
With him, there is no performance. No eggshells. No pressure. Just alignment.
We walk together, in purpose. I now have a partner who is in service to me, not in competition with me. A partner who lightens my load. Mentally, emotionally, and spiritually. He helps me think. Helps me build. Helps me breathe. He makes my life easier, and that is something I had never experienced before.
I still reinvest in my love life by continuing to work with Anwar. His programs have taken me from dating, to courting, to exclusivity, to engaged, and now to being married. Because each of those phases required a new version of me. Because I had never been here before.
@shirleyvernae I hadn’t been on a single date in 2 years. Met my fiancé last year and got engaged 2 months ago. You’re the CEO of your love life. It’s time to act like it ❤️ # CEO ##Fiancé##Engaged##Relationships##Dating##Engagement
Through Anwar’s program, I was gifted the most pivotal mindset shift of them all:
That love doesn’t have to feel like a struggle. And that’s my new standard.
One of the most powerful things Anwar said to me was, “You can’t do the wrong thing to the right guy.” And that truth set me free.
Before working with him, I thought love had to be proved. Performed. Earned. I thought I had to be perfect. Healed. Small enough to fit into someone else’s version of love. But that was never true.
There are men who are devoted to creating ease in your life. Men who see your softness as strength and your boundaries as beauty.
My now-husband, Ty, is one of them. He is steady. He is consistent. And no matter how much I struggled, no matter how I tried to self-sabotage, he stayed anchored in one mission: to bring ease, to bring peace, to bring safety.
So the shift? I stopped performing. I started discerning. I raised my standards. I stopped doubting. And I let myself be held.
Yeah, the biggest shift was realizing I am worthy of love that doesn’t come with chaos. Love that’s safe. Love that’s solid. Love that’s soft.
That’s what happens when you stop settling and start showing up with faith, clarity, and strategy. That’s what happens when you become the CEO of your love life.
Being the CEO of my love life meant I stopped outsourcing it to luck, fate, or vibes. I no longer left it up to chance or timing, or wishful thinking. Just like I build businesses with vision, strategy, and intentional partnerships, I built a love life that reflects those same values.
A good CEO doesn’t try to do it all alone. A good CEO casts vision, brings the right experts to the table, delegates with wisdom, and trusts the process. That’s exactly how I approached love. I partnered with God. I partnered with mentors. I aligned my actions with my desires. That’s not control, that’s stewardship. And that’s what changed everything.
I knew sharing my journey online was going to stir something up. And it did. Some people were inspired. Some were uncomfortable. But their discomfort wasn’t about me. It was about what my story confronted in them: scarcity, shame, old beliefs about what’s “worth it” and what’s not.
And I’m okay with that. I’m not here to be liked. I’m here to be aligned. That’s my assignment.
To the woman who’s feeling discouraged, let me say this: Time is a tool, don’t let it become your tormentor. You are not late. You are not behind. You are not disqualified. Your desire for love is not shameful, it’s sacred.
Don’t let what society says, what the media projects, or what a non-believer has spoken over you define what’s possible. The only thing that’s true is what God has said. And God has said, “All things are possible to him that believes.”
If you’re feeling stuck, let that be your invitation to do something different. You don’t have to do this alone. Ask for help. Get support. Find a coach, a mentor, a couple you admire—not the shiny ones on social media, but the ones who’ve walked through fire and still chose each other.
Date with intention. Choose love on purpose. Marriage is a gift from God, and it is never too late to receive it. There is strength in being seen, supported, and walking in purpose together.
And for my Black women especially, softness is your superpower. Discernment is your birthright. You are the prizeand the picker. Dating with intention isn’t about being aggressive, it’s about being aligned.
We are not desperate. We are divine. Even in your healing, even in your becoming, know this: you can never do the wrong thing to the right guy.
And the right guy? He’ll meet you right there: in your wholeness, and in your work-in-progress.
To keep up with Shirley Vernae Williams and her journey as a storyteller, producer, and love life CEO, follow her on Instagram @shirleyvernae and learn more about her work at williebstudios.com.
Featured image courtesy of Shirley Vernae